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Featured Properties

$19,900,000
4 Beds ⋅ 5 Baths
Rarely… does such a unique, well-designed, constructed, and maintained world-class equestrian facility grace the international real estate market. Spanning 510 preserved acres, this iconic equestrian estate boasts a rich legacy and unparalleled amenities, including a state-of-the-art equestrian training facility built by B&D Builders, a nationally renowned custom builder. RiverEdge Farm is synonymous with world-class equestrian training, ideally suited to any discipline. The farm has previously housed numerous Olympic dressage and three-day event horses, operated as a top-class private thoroughbred breeding facility, and most recently served as a training mecca for world-class dressage. At the heart of the property is a spectacular 31-stall, 45,000-square-foot indoor dressage show barn. Built with unmatched craftsmanship and old-world charm second to none. Visitors are welcomed through a charming, covered porch and elegant, glass-paneled double doors into a grand reception area featuring a central stone fireplace and a private meeting room, all adorned with custom millwork throughout. Overlooking the 100’ x 200’ indoor dressage arena are stunning glass-enclosed observation areas on both the first and second floors, that are brilliantly filled with natural light and character. This impressive space includes twin service bars, a conveniently located commercial-grade kitchen, and a spacious area ideal for entertaining. An ornate wide-plank staircase leads to a lofted second level with private office suites, an exercise room, and a lounge area. The barn itself is thoughtfully designed, featuring barreled ceilings, six grooming/wash stalls, two well-appointed tack rooms, a central eat-in kitchen/break area, a laundry room, and a three-season sitting room offering panoramic views through grand window walls on two sides. The barn’s layout seamlessly flows through a bank of 31 spacious (mostly 14’ x 14’) stalls, curving into an additional wing with even more accommodations. Complementing the equestrian facilities is a beautifully appointed 9,000-square-foot brick manor home of Georgian architectural style, offering four bedrooms and 3 full & 2 half bathrooms. This wonderful home features an updated kitchen, brick and antique wood flooring, beamed ceilings, a sunken living room, multiple fireplaces, a spacious game room, and a detached three-car garage. The extensive grounds are thoughtfully and professionally landscaped. It artfully blends traditional character with modern conveniences—perfectly suited for today’s lifestyle. Also included within this breathtaking property is a luxurious guest home featuring a chef’s kitchen and an enclosed timber-framed pavilion over a heated indoor pool. Additionally, there is a 15-stall center-aisle block barn with a six-horse Kraft Eurocizer, as well as numerous ancillary operational buildings, including a fully functional brick office building—and numerous double-fenced fields and paddocks with approximately 10 miles of four-rail post-and-board fencing offering unparalleled views throughout the farm. RiverEdge is set within one of Maryland’s largest agricultural preservation areas and is protected by a conservation easement, ensuring its beauty and legacy for generations to come. The property includes 4 parcels: 0802016206 - 109.4 acres, 0802019078 - 186.7 acres, 0802029049 - 106 acres, and 0802029537 - 109.4 acres.

1455 Cayots Corner Rd, Chesapeake City

Listing courtesy of Monument Sotheby's International Realty. Contact: 3026546500
$18,000,000
4 Beds ⋅ 3 Baths
Rare opportunity to purchase 26 + acres of waterfront on the South River! This just does not happen! 5 separate lots. Zoned MA2, R1, RLD/OS. Features 1 lot with brick rancher 4 bedrooms and 3 baths. Deep water pier with gazebo and boat house. Total water frontage is approx. 1200 feet. Endless opportunities to develop this gem. Family compound, private estate, horses, lots of privacy and nature. Near South River Bridge. Selling as an entire package. Includes parcels 157,158, 378,159 and 154. Property Tax Records. 020200006760600, 020200006764800, 020200006765200, 020200006765000, 020200090083947. Agent related to owner. Appointment required.

27 Old South River Rd, Edgewater

Listing courtesy of Hoffman Real Estate Group, LLC. Contact:

$16,500,000
7 Beds ⋅ 10 Baths
Set in the heart of Maryland’s storied Worthington Valley, Sagamore Farm offers an extraordinary opportunity to own one of the most iconic estates in American Thoroughbred racing. Founded in 1925 by Isaac Emerson and later entrusted to Alfred G. Vanderbilt Jr., Sagamore rose to international prominence as a premier breeding and training ground, producing legendary racehorses and hosting generations of equestrian excellence. Today, the estate spans over 524± acres of rolling pastures framed by classic white board fencing, thoughtfully restored to honor its legacy while supporting modern operations. At its center, a stately 16,000+ square foot residence offers gracious, light-filled living spaces designed for both refined entertaining and everyday comfort. A richly appointed library provides a quiet retreat, while the formal dining room, scaled for memorable gatherings, sets the stage for elegant evenings. Each of the six upper-level bedrooms features its own en-suite bath, creating a private sanctuary for family and guests alike. The equestrian facilities are equally exceptional. A 3/4-mile (six-furlong) Tapeta synthetic training track delivers superior footing, complemented by the iconic Clocker’s Tower with a viewing lounge, kitchenette, and dining area offering an elevated vantage point for overseeing training or hosting with ease. The property includes a comprehensive collection of barns, including a stallion barn, training barn, broodmare barn, and foaling barn, along with expansive turnout paddocks. Vanderbilt's original home remains on the property, providing residence for a general manager, while the well-appointed bunkhouse provides comfortable accommodations for staff and jockeys. Also on the grounds is an historic natural spring house, adding a distinctive nod to the land’s enduring heritage. With its unmatched pedigree, world-class infrastructure, and timeless setting, Sagamore Farm represents a rare offering equally suited for a premier Thoroughbred operation or a visionary expansion into additional equestrian disciplines. A legacy property of remarkable scale, significance, and possibility. With effortless access to I-83, I-695, BWI Airport, Washington, D.C., New York, and central to the world’s most prestigious racing venues, Sagamore Farm stands ready for its next chapter.

3366 Belmont Ave, Glyndon

Listing courtesy of Monument Sotheby's International Realty. Contact: 4437087074
$15,000,000
6 Beds ⋅ 5 Baths
OPEN HOUSES BY APPOINTMENT. PLEASE COME AND TAKE A LOOK AT THIS MAGNIFICENT 500 ACRE ESTATE WHERE THE FOUNDING FATHER'S ONCE MINGLED! Mulberry Fields is one of those rare places where the land itself tells the story. The mile-long cedar avenue announces the approach, its rows planted at an ever-widening angle to draw the eye toward the Potomac below, a feat of 18th-century landscape design so precise it has appeared in gardening textbooks for centuries. At the end of that drive stands the last surviving Georgian manor house in St. Mary’s County, a ca. 1755 brick estate where the center hall, great room, and dining room are paneled in raised wood from floor to ceiling, the original moldings, doors, and mantels intact after nearly 270 years. Beyond the manor, two Georgian brick dependencies anchor a formal north courtyard, and the grounds unfold across just under 500 acres of fertile land before meeting 1,700 feet of white sand Potomac riverfront. There is simply no other property like this on the Eastern Seaboard.

19700 Mulberry Fields Rd, Leonardtown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$12,975,000
6 Beds ⋅ 11 Baths
This extraordinary gated 20-acre waterfront estate, featuring a French-inspired stone residence, sits prominently along the banks of the Severn River just minutes from downtown Annapolis and under an hour from Washington, DC. With coveted western exposure, the property offers breathtaking, year-round sunsets and over 23,000 square feet of combined living space across the main house, guest house, and carriage house—all set amid rolling lawns, formal gardens, mature trees, and natural surroundings. The main residence is designed for both grand entertaining and comfortable living, with ten sets of French doors opening to terraces and gardens. A dramatic two-story foyer with limestone and marble inlays leads to a soaring great room anchored by an 18th-century French carved limestone mantel. Additional main-level spaces include a formal dining room, library, and music room—each with its own fireplace—and a gourmet kitchen featuring dual marble-topped islands. Upstairs, an open gallery overlooks the great room and grounds, while the expansive primary suite offers a fireplace, private sitting room, and waterside balcony with sweeping river views. The lower level is equally impressive, with a family room, billiards room and bar, a striking stone wine cellar with tasting room, media room, full gym with bath and sauna, and an additional bedroom suite. A separate wing provides a dedicated art studio or craft space, complemented by a motor court and two three-car garages. Outdoor living is equally refined, with manicured lawns and gardens, an expansive patio, outdoor kitchen, hot tub, and charming details including a gardening shed, chicken coop, and raised beds. The approximately 6,000-square-foot guest house is ideal for hosting, centered around a pool with a covered veranda, outdoor fireplace, bar, and gazebo—all with water views. Inside, it offers spacious living and dining areas with a shared stone fireplace, three bedrooms, two full and two half baths, and a full catering kitchen with Viking appliances. A breezeway connects to the carriage house with an additional three-car garage. The estate’s 900 feet of shoreline is complemented by a 350-foot deep-water pier (8–9' MLW) with four slips, including two accommodating 60-foot vessels, and two boat lifts—perfect for boating, sailing, and enjoying life on the Severn River and Chesapeake Bay.

938 Old County Rd, Severna Park

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$12,950,000
6 Beds ⋅ 9 Baths
Imagine arriving home each day to a place where the pace slows, the views stretch for miles, and every amenity for recreation, relaxation, and entertaining is right outside your door. Tucked away along the Chesapeake Bay, this extraordinary waterfront retreat offers a lifestyle that few properties can match, a private oasis where luxury and nature exist in perfect balance. Originally constructed by the renowned Pyramid Builders and later transformed through an extraordinary $7 million top-to-bottom renovation, also completed by Pyramid Builders, the estate has been reimagined to an uncompromising standard. Every space, finish, and amenity was thoughtfully designed and curated to create a residence that is as functional as it is beautiful, blending timeless craftsmanship with modern luxury. State of the art features include the Crestron Home Automation and integrated Lutron lighting systems while the modern luxuries entail top of the line Miele appliances including a built-in coffee maker, microwave and convection oven, BlueStar range, radiant heated floors in all bedroom bathrooms and much more. Here, days can begin with coffee overlooking the pond and its abundant wildlife, followed by a swim in the heated saltwater pool, a match on the tennis or pickleball court, a workout in the gym, or a stroll down to the sandy beach. Evenings are spent gathered with family and friends around the pool and hot tub, watching the game on the hydraulic television that rises from the landscape, enjoying a glass of wine from the tasting room, or simply taking in the stars above the Bay. The ever-changing waterfront scenery, southern exposure, and remarkable sense of privacy create a backdrop that feels more like a luxury resort than a private residence. Designed for those who believe home should be a destination, the property offers an incredible collection of indoor and outdoor amenities rarely found in a single estate. Tennis, pickleball, basketball, a climbing wall, playground, in-ground trampoline, expansive lawns, sandy beach, pond with fountain, indoor racquetball court with basketball and volleyball capabilities, golf simulator, game room, fitness center, indoor lap pool, infrared sauna, wine tasting and cellar area, and countless spaces to gather ensure there is always something to enjoy for every generation. The residence itself is beautifully designed and thoughtfully appointed, with spacious living and entertaining areas, a wraparound screened porch that embraces the waterfront setting, private ensuite bedrooms throughout, and a dedicated guest or in-law suite that welcomes family and friends in comfort and style. Abundant storage, an attached two-car garage, and a detached garage with additional space for vehicles, golf carts, recreational equipment, and storage provide the functionality expected of a property of this caliber. What makes this estate truly special is not simply the remarkable list of amenities—it is the feeling it creates. The extraordinary combination of peace, beauty, privacy, and convenience is increasingly difficult to find. Just minutes from Annapolis, yet seemingly a world away, this is the kind of property where children spend their days outdoors, guests never want to leave, and every sunset reminds you why you chose to call it home. A rare opportunity to own a true Chesapeake Bay waterfront compound where every day feels like a vacation, every detail has been thoughtfully considered, and the lifestyle is every bit as exceptional as the home itself. Welcome Home!

2045 Maidstone Farm Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$12,500,000
5 Beds ⋅ 7 Baths
A rare opportunity on Spa Creek, this fully reimagined Murray Hill residence offers an extraordinary waterfront lifestyle just moments from downtown Annapolis. Completed in late 2023 after a full ground-up rebuild, the home spans 5,900+ sq. ft. of impeccably crafted living space, where natural materials, refined architectural details, and top-tier systems create a seamless blend of comfort and sophistication. Set on just under a half acre of level waterfront, the property showcases one of the most complete private pier systems in the area: a heavily built main pier, two floating docks, and three boat lifts (16,000lb, 8,000lb, and 2,500lb), plus lighting, water, 30/50-amp shore power, Tide Slide moorings, and 6' MLW at the 70' T-head. A charming boathouse and waterside deck capture the magic of Spa Creek from morning to sunset. Outdoor living is exceptional. A stunning 40' x 20' PebbleTec saltwater pool—rebuilt in 2024—anchors a series of Ipe decks and natural stone patios and decks designed for effortless entertaining. The outdoor kitchen with piped natural gas grill, refrigerator, and sink extends gatherings well into the warm months, while covered and uncovered spaces offer year-round enjoyment. The exterior speaks to enduring quality with Carderock stone foundations, mahogany trim and ceilings, Loewen windows, Canadian cedar siding, copper gutters and flashings, and custom mahogany entry doors. A detached heated and cooled two-car garage includes a beautifully finished upper level with kitchenette, laundry, living/sleeping area, and private bath—ideal for guests or an au pair. Inside, the home is defined by warm natural luxury featuring a stunning barrel vaulted mahogany ceiling with cove lighting. Additional curated details include: mahogany doors, black bronze hardware, 5" Cumaru flooring, custom cabinetry, and extensive millwork throughout. The chef’s kitchen features Sub-Zero and Wolf appliances with granite and soapstone surfaces. The main level Primary suite with inspiring view of pool and waterfront provides convenience and options for aging in place. The lower-level recreation spaces provide a relaxed retreat with a private bedroom suite, family room, wet bar, gym and full laundry room. An abundance of thoughtful design is presented throughout the home with multiple wet bars, radiant heated tile floors in five bathrooms and the main-level bar, and four separate laundry areas. Less than half a mile from Church Circle, this residence delivers the rare ability to live on the water while enjoying the full walk-everywhere lifestyle of historic Annapolis. This is Spa Creek living at its finest: sophisticated, effortless, and undeniably special. Welcome Home!

5 Franklin St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$11,995,000
4 Beds ⋅ 5 Baths
Private Island at 1546 Teal Drive, Ocean City, Maryland is a truly unique offering — the bay's only island estate. Included is an adjacent buildable waterfront lot just inside the entrance gates before crossing the private bridge. The improved .29-acre parcel features approximately 95 feet of bulkheaded shoreline with boardwalk, paved driveway, irrigation, and landscaping, offering flexibility for a future guest house or single-family residence, additional parking, or expanded waterfront enjoyment. Located off 15th Street in downtown Ocean City, the property offers seclusion and accessibility, 3 blocks to the Boardwalk and beach, minutes to the Ocean City Inlet and Assateague Island by boat, and a block from Harbor Island, home of the world-renowned White Marlin Open. Hidden behind a brick wall and accessed through a 6-foot gate, the arrival continues across a private 120-foot vehicular bridge from Mallard Island. The island encompasses more than 3 acres of native marshlands and coastal landscape with panoramic views of the open bay, the Rt. 50 Bridge to the south, Rt. 90 Bridge to the north, and the rare combination of breathtaking sunrises and sunsets across the water. Architecturally, the home is an iconic shingle-style residence inspired by Nantucket architecture, with exterior renovations and enhancements by renowned Lyman Perry Architects Ltd. of Nantucket, Massachusetts. The approximately 5,000-square-foot home features custom woodworking, Carlisle wide-plank hand-finished pine flooring, new Andersen doors throughout, approximately 3,250 square feet of wraparound decking, and expansive water views. Upon entering, a dramatic 24-foot atrium features a 12-foot by 15-foot overhead skylight and floor-to-ceiling Coral Rock fireplace feature connecting the surrounding living spaces. Designed to maximize open bay views throughout, the main living area features custom built-in cabinetry and flows into the separate dining and gathering spaces. The kitchen/family room creates an inviting area for entertaining, with custom solid birch painted cabinetry by Premier Cabinetry of New Holland, Pennsylvania, and a 5-foot by 8-foot teak island countertop. A custom wood spiral staircase provides secondary access between the main and upper levels. The main level also includes a home office with built-in cabinetry and pull-out file storage, plus an additional guest bedroom and full bath. Upstairs, an open bridge hallway overlooks the atrium while separating the primary suite from two guest bedroom suites. The four-room primary suite includes a bedroom retreat with bayfront deck, sitting/entertainment/dressing room with vaulted ceilings, custom cherry wood built-ins and four closets, en-suite bath with double vanity and dressing table, and a second dressing room with vaulted ceilings, four double-door deep closets, and an arched window with window seat dividing two built-in tall chests. Two additional bedrooms each feature en-suite baths and private decks. Outdoors, an island retreat features a pool and spa by Sea Glass Pools, expansive decking, gazebo bar with cabinetry and quartz countertops, full bath with shower, docking, 10,000-pound boat lift, and fish cleaning station. Significant recent investments include bulkhead improvements, reinforced helical pilings, bridge renovations, active security and surveillance systems, and maintained structural and mechanical systems. Surrounded by abundant birdlife and endless open-water vistas, this distinguished estate embodies timeless elegance.

1546 Teal Dr, Ocean City

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4105247000
$11,700,000
6 Beds ⋅ 9 Baths
Live authentically. Align forces with the internationally renowned designer Steven Gambrel. Cultivate your vision with a designer who draws inspiration from vernacular architectural details of the region and was honored as one of “today’s greatest talents in Architecture and Design” in Architectural Digest’s “AD 100.” A true artist and masterful conductor of form. Steven subscribes to the importance of properly proportioned structures and details, partnered always with a carefully curated collection of vintage, antique, and custom furniture designed by Steven himself. Embark on a journey to create a destination for you and your family. Enduring architecture and honed materials give you the experience of feeling settled and inspired all at once. The award-winning Delbert Adams Construction Group is here to help you realize your vision in all its brilliance. This 20-acre site is worthy of a legacy estate. Raw in its current state, awaiting to be shaped by new stewards. Two separately deeded building sites exist. Elevated main estate site overlooking idyllic pond teeming with life. Relish the long treelined drive with iconic old stone entry monuments. Glorious private setting. Ample room for pool, guest house, gardens, greenhouse, tennis courts, and whatever else might be on your mind. Rock outcroppings. Ponder the benefits of building exactly what you desire. Lively meandering stream and walking paths. Unleash your vision for living with an incredibly talented team to get you there. A site where the synergy of your creativity is elevated with the land. Tucked away in the heart of Greenspring Valley. One of the few sites left in the Valley. Incredibly accessible to Falls Rd, 83, and 695. Conservation easement exists. Photos are concepts for inspiration. Please do not visit the property without an appointment. The art of uniting human and home. Please see related listings. The seller is doing some site work and we will be back in the fall: Hillside | Land | MLS# MDBC2007018 933 Hillside Rd | Land | MLS# 1000113931- Temp off 933 Hillside Rd | Land | MLS# MDBC2026716 -Temp off 933 Hillside Lot A | Residential | MLS# MDBC2026352- Temp off 933 Hillside Lot A | Farm | MLS# MDBC2026534

933 Hillside Lot A, Lutherville Timonium

Listing courtesy of Krauss Real Property Brokerage. Contact: (410) 804-7921
$11,500,000
5 Beds ⋅ 6 Baths
Experience one of the few Annapolis waterfront estates where you can leave your private dock and arrive at City Dock in minutes. Ideally situated on Spa Creek, this exceptional property captures the essence of Annapolis waterfront living with panoramic water views, unobstructed views of the Annapolis skyline, and endless opportunities for boating, kayaking, paddleboarding, and entertaining. Cruise by boat to downtown Annapolis, waterfront restaurants, ice cream shops, and the historic City Dock, or enjoy spectacular views of the Blue Angels, fireworks, and the annual boat parade from your own private retreat. Set within an exclusive enclave of only three prominent waterfront residences, this property offers a rare combination of privacy, convenience, and lifestyle. The waterside heated saltwater pool, expansive Ipe deck, and beautifully landscaped grounds create the perfect setting for entertaining family and friends. Host sunset dinners, summer gatherings, or relaxed afternoons outdoors while enjoying the water views and the sparkling lights of the Annapolis skyline. Surrounded by lush boxwoods and specimen plantings, the grounds provide a peaceful escape just minutes from downtown. Architecturally distinctive and thoughtfully updated, the residence combines refined design with comfortable waterfront living. Extensive renovations by Pyramid Builders showcase exceptional craftsmanship, including a dramatic marble foyer, floor-to-ceiling windows, solid wood doors, and rich stained black oak flooring. The gourmet kitchen features Sub-Zero refrigeration, a white six-burner Viking cooktop, high-gloss Premier cabinetry, Neolith porcelain countertops, designer lighting, and a striking floating staircase. A custom marble-topped bar provides an ideal space for entertaining. Offering 4–5 bedrooms, 5 full baths, and 1 half bath, including a desirable first-floor bedroom suite, the home provides flexibility for family and guests. A two-car garage, generous parking, and deep-water pier complete this exceptional Annapolis waterfront offering. This is more than a home—it is a rare opportunity to experience the very best of Annapolis living, where boating, entertaining, and downtown charm come together in one extraordinary setting.

8 Spa View Cir, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$11,000,000
4 Beds ⋅ 5 Baths
Presenting "Middleville" (est. 1880), one of the largest waterfront farm and residential estates currently available in the State of Maryland. Spanning over 662 pristine acres in Talbot County, this once-in-a-lifetime landholding features 1.8 miles of shoreline and a world-class infrastructure for luxury living and elite conservation. The Residences & Amenities: The centerpiece of the Estate is the Tidewater Colonial Main Residence, meticulously renovated in 2025. Blending Coastal Charm with modern luxury, the home features: Gourmet Kitchen, equipped with custom cabinetry and top-tier luxury appliances. Waterfront Great Room, an architectural masterpiece with floor-to-ceiling glass offering expansive views of the Chesapeake Bay. Owner’s Wing, a first-floor primary suite featuring dual bathrooms and dual walk-in closets. Refined Finishes: Time-period hardwood flooring throughout, four brick wood-burning fireplaces, and durable HardiePlank siding with a metal roof. Outdoor Living: A tree-lined drive leads to a resort-style grounds featuring a swimming pool, pool house, built-in hot tub, and dedicated pickleball and basketball courts. Estate Infrastructure: 3-car garage, geothermal heating, backup generator, professional hardscaping and multiple barns and storage buildings . Additional Housing: The compound includes three private guest houses and a dedicated caretaker’s residence . The Land & Conservation: Comprised of five distinct parcels, the acreage is a diverse blend of productive agriculture and natural sanctuary. Acreage Breakdown: 390+/- acres of fertile, income-producing cropland and 175+/- acres of mature forest. Waterfowl & Wildlife: A premier destination for sportsmen, the property includes a 7+ acre stocked fishpond/waterfowl holding and six well-fed, water-controlled waterfowl impoundments designed for quality game management. Shoreline & Pier: Over 1,200 feet of shoreline revetment protects the coast. The private pier is equipped with two boat lifts and additional mooring capacity. Middleville is a "turn-key" legacy estate on Maryland’s Eastern Shore, offering a rare fusion of historic significance, 2025 modern luxury, and vast natural resources. In an era where land is the ultimate luxury, this is a unique opportunity to secure one of the region's most significant holdings.

29245 Howell Point Rd, Trappe

Listing courtesy of Holiday Real Estate. Contact: 4105247700
$10,850,000
4 Beds ⋅ 7 Baths
An extraordinary expression of waterfront luxury, this architecturally significant estate represents a rare convergence of world class design, craftsmanship, and lifestyle. Located within the prestigious enclave of Wimbledon Farms, surrounded by grand estates and moments from local vineyards and equestrian facilities, the residence was masterfully conceived by acclaimed architect Scarlett Breeding and flawlessly built by Pyramid Builders. A complete refit elevated the home to an uncompromising standard where timeless architecture and modern sophistication exist in perfect harmony. An enchanting winding crushed gravel driveway framed by Belgian block curbing sets the tone for the remarkable experience that awaits. Perfectly positioned with western exposure, the property captures breathtaking sunsets as golden light melts into the horizon across the river and the surrounding landscape. Professionally designed landscaping creates a lush resort like setting that enhances the home’s striking architectural presence. Inside, high lacquered woodwork, bespoke millwork, hidden passage doors, attention to detail, and coffered ceilings create an atmosphere of refined sophistication. Ultra luxe Chesneys fireplace surrounds anchor multiple living spaces with warmth and elegance, while expansive walls of glass frame sweeping water views and seamlessly connect the indoors with the surrounding waterfront setting. A richly appointed wood-clad office with custom built ins offers an executive retreat designed for both privacy and inspiration. At the heart of the residence, the extraordinary St. Charles kitchen rivals those found in internationally celebrated estates, featuring Premier custom cabinetry, a statement Le Cornue range and island, exquisite fixtures, and an artisan-crafted focal point range hood, all designed for elevated entertaining and effortless daily living. Outdoor living reaches resort caliber with an elevated spa and a spectacular four sided overflow vanishing edge pool, where the waterline sits flush with the pool edge, creating a seamless visual connection to the river beyond. Exotic Ipe hardwood decking surrounds the pool and expansive rear terrace, while pergolas and a screened porch provide beautifully designed spaces for entertaining and relaxation. A new private pier, private beach, and panoramic river and pond views complete this extraordinary waterfront lifestyle. The upper level offers four luxurious ensuite bedrooms, including a phenomenal primary suite with sweeping water views, barrel ceiling, a fireside sitting room, a boutique inspired dressing gallery, and a spa quality bath with a soaking tub overlooking the water. Integrated Control4 home automation delivers effortless comfort and convenience throughout. Tucked away on the coveted Annapolis Neck peninsula, Wimbledon Farms offers a rare blend of tranquility, exclusivity, and convenience. Just moments from Downtown Annapolis and major commuter routes, the setting feels worlds away, defined by peaceful surroundings and an unmistakable sense of retreat. Encompassing only 19 estate homesites, this intimate waterfront enclave is gracefully bordered by Harness Creek and the South River, creating a breathtaking backdrop for both sunrise and sunset vistas. Residents enjoy a warm yet private community atmosphere, highlighted by occasional neighborhood gatherings and an expansive marina on protected Harness Creek, a prized deep water haven known for its calm, sheltered waters and exceptional boating access. Welcome Home!

3344 Harness Creek Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$10,200,000
7 Beds ⋅ 7 Baths
Live authentically. Magnificent stone estate tucked away overlooking Worthington Valley and beyond. Upper Melinda awaits perched on 235.00+/- acres. Commanding views of the valley complement the strength grandeur of this enduring architectural masterpiece. Relish the meandering drive home through lush woodlands. A sanctuary of tranquility and serenity. Crafted by acclaimed architect Louis McLane Fisher and adorned by the legendary Baltimore native, Billy Baldwin. Discover the whispers of Baldwin’s timeless touches lingering in dashes of red lacquer accents and smokey mirrors throughout. Within, nine roaring fireplaces beckon conversation and radiate comforting warmth. Main level owner’s suite. Transform your nocturnal journey as you gaze across the valley before falling into restful slumber. Your inner chef will flourish in the cooking space. Partake in lighthearted fun and competition in the basement game room. Original cork flooring embellished with exotic animal inlays; intact. Immerse yourself in the opulence of rich landscaping as you explore your outdoor haven. Savor the stillness and go for an invigorating round of laps in the sublime pool.. Recharge in the ambiance. An expansive stone terrace embraced by abundant greenery beckons for an elevated outdoor dining experience. Other worldly views that are hard to grasp. A palpable depth of wonder permeates. A sensory experience. Vistas that mirror paintings. Gaze over glistening ponds in the distance. Truly a living canvas from which to paint the next chapter of your life. A legacy property. 5 +/- miles of extensive trail network throughout the grounds. Revel in the extreme privacy. Indulge in the vast beauty that unfolds around you. Enchanting stone guest house recently renovated. Four income generating tenant houses convey that are unable to be divided. Cultivate your existence. The art of uniting human and home. Do not drive to property without an appointment. Property is subject to conservation easement.

Glyndon

Listing courtesy of Krauss Real Property Brokerage. Contact: (410) 804-7921
$10,000,000
14 Beds ⋅ 14 Baths
This offering marks an extraordinary opportunity to acquire one of North America’s most prestigious properties. While the 437.5 acre farm is globally celebrated for its history of breeding, training, and raising excellence and many world-class sport horse champions, the focus now turns to the sale of the physical estate, a masterpiece of equestrian infrastructure and natural beauty now available for its next chapter. The property is defined by its remarkable landscape, featuring 200 wooded acres of mature trees, 220 acres of pastureland, and 15 acres of impervious structures across the gently rolling terrain of Cecil County. Bordered by 1.3 miles of tranquil waters of the Octoraro Creek, the land offers a rare combination of high-performance utility and serene privacy. The sale includes comprehensive, established equestrian infrastructure, highlighted by a 36-stall main barn, 2 outdoor arenas, 12 fields, 31 paddocks, 14 dwellings, 2 additional barns, and numerous equine facilities that have served as the benchmark for elite sport horse development for decades. The true value of Hilltop Farm’s footprint lies in its versatility; it is a canvas limited only by the scale of one’s imagination. While its equestrian pedigree is unrivaled, the estate invites a bold repurposing as a world-class Agri-Tourism Destination or a Private Legacy Compound. The riverfront and woodlands are perfectly suited for a Luxury Wellness Retreat, with riparian trails just a stone's throw from the urban corridors of Philadelphia, Baltimore, and DC. As this historic operational chapter concludes, the property is now positioned for a new curator to inherit a landscape of immense function and beauty. This is a rare chance to own a sanctuary that has been both a stage for international sport and a community standard-bearer. This property includes multiple parcels and should be referenced in conjunction with MLS# MDCC2020402 (Tax ID: 0806025811) and MLS# MDCC2020404 (Tax ID: 0806012450).

1089 Nesbitt Rd, Colora

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$9,995,000
7 Beds ⋅ 10 Baths
7112 Natelli Woods Lane, a stately new construction designed by GTM Architects. Envisioned as a seamless union of timeless elegance and modern luxury, this 13,000+ square foot estate rests on two sweeping acres of manicured landscape. A striking all-glass and steel pivot front door leads into a dramatic foyer, flanked by a formal study and grand dining room. The interiors are defined by bespoke finishes, including 9-foot Barausse Italian doors throughout, custom Italian cabinetry by Stossa Metropolis in the kitchen and bar, and meticulously tailored closets by ARAAN of Italy. The heart of the home—an exquisite chef’s kitchen with Miele appliances—flows effortlessly into a soaring family room with 22-foot ceilings, setting the stage for refined entertaining. Ambiance is perfected by a state-of-the-art Lutron lighting system, offering over 15 million combinations, paired with custom automated Lutron shades. A butler’s pantry, scullery, elevator, and stylish powder room add convenience. The main level features a lavish primary suite retreat with a spa-inspired bath, sitting room, and access to a covered porch. Additional highlights include a laundry room, pool bath, and five-car garage. A 30'x15' covered porch with arches, columns, heating, and a dual-sided fireplace invites all-season enjoyment with a view of the pool beyond. Upstairs, discover five secondary bedroom suites, an optional second primary suite, and a sunlit family lounge overlooking the grounds. The fully finished lower level is designed for indulgent recreation with a cinema, bar lounge, golf simulator, gym, billiards area, and a private guest suite.

7112 Natelli Woods Ln, Bethesda

Listing courtesy of TTR Sotheby's International Realty. Contact: 2029750873
$9,950,000
5 Beds ⋅ 10 Baths
Live authentically. Sunny Hill Farm circa 1937. Brilliantly designed by William McMillan, storied architect. McMillan was also commissioned locally to design Alfred Vanderbilt's residence at Sagamore. McMillan married Grace G. Roosevelt, granddaughter of Theodore Roosevelt. They lived their days out at Sunny Hill. This is the second time it has been offered. A significant estate perched on 261 glorious acres with spectacular panoramic views of Worthington Valley. Masterful architecture. This English Country estate was sited in a way that dances with the sun. Your sense of arrival is punctuated by a very purposeful Moon Gate. I can only imagine an architect who is just as avid of a yachtsman would incorporate such a feature to connect with a framed view of the cosmos. Remarkable. Poetic interior and exterior courtyards grace every space. Soothing fountains are placed just so. Artistically framed views abound. Dazzling use of expansion and contraction. Sunny Hill will have a profound effect on you. A place to be cherished for generations. A cultivated trail network exists... adventure through vast woodlands, streams, orchards, and rolling farmland. You will experience microclimates from one end of the property to the other. Teeming with wildlife. Stroll seamlessly into the great outdoors and never miss a sunrise or sunset from one of your many terraces. Exquisite pool and hot tub. Ample space to curate pasture and equestrian facilities if desired. Greenhouse. Amish built five bay barn. Additional potential densities. Cultivate your existence. The art of uniting human and home.

3600 Butler Rd, Glyndon

Listing courtesy of Krauss Real Property Brokerage. Contact: (410) 804-7921
$9,900,000
5 Beds ⋅ 6 Baths
Situated on one of the finest residential parcels in the country, Ship’s Point, is an estate with few rivals anywhere, at any price. The completely private 13+/- acre estate includes a deep water pier, and 270-degree views at the confluence of Trippe’s Creek and the Tred Avon River. The south-west facing manor house has been meticulously renovated by renowned builder Winchester Construction. A visit is necessary to understand the rarity of the views provided by the nearly one-half mile of shoreline that surrounds this home.

6010 Shipyard Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$9,500,000
6 Beds ⋅ 5 Baths
This 37-acre Waterfront Estate in the desirable West Ocean City Community of Captains Hill stands among Worcester County’s true legacy properties. A rare combination of Coastal Luxury, privacy, acreage and future opportunity. Set on a expansive rise overlooking the bay, the Estate commands sweeping water and skyline views that shift elegantly from sunrise to the golden glow of sunset. A long driveway leads you to the 8000+ Sq Ft Coastal Residence, a grand yet serene retreat surrounded by park-like grounds and mature landscape that creates an atmosphere of total privacy. The main Estate and grounds encompass 27 acres that feature a diverse landscape designed for both beauty and functionality. Such highlights include a 3-acre freshwater pond that anchors the properties tranquil setting, an outdoor pool with surrounding deck ideal for families and entertaining, an expansive lawn for gatherings and pets, a large covered porch perfect for enjoying the broad water views and nature, covered parking entrance and a three-car garage. The residence itself offers the architectural presence and scale expected of a Coastal Estate of this magnitude, with generous living spaces, impressive ceiling heights and endless potential for customization or enhancement. In addition, this Estate offers additional parcels and development potential that allows for flexibility for future use. Included in the offering is a 2.73-acre Waterfront Lot and 20 plated lots with their own road frontage. This rare land portfolio provides exceptional opportunities, ideal for a private compound, multi-generational retreat, curated development or long-term investment that makes this property uniquely valuable. Opportunities of this size, location and versatility rarely ever come to market. With commanding views, coastal proximity, and expansive acreage, this Captain’s Hill Estate stands as one of the region’s premier offerings, a property with both present-day grandeur and limitless future potential. A Coastal Treasure without equal.

12903 Windy Dr, Ocean City

Listing courtesy of Holiday Real Estate. Contact: 4105247700
$8,995,000
6 Beds ⋅ 5 Baths
Set on 93 private acres with 6,100 feet of shoreline along the picturesque Sassafras River and Cox Creek. The estate includes a main house, guest house, pool house and riverside pavilion, offering ample delightful space for large groups to gather, unwind and experience the activities and natural beauty of the upper Chesapeake. Showcasing exceptional design, materials, craftsmanship, the living spaces are framed by expansive views of the Sassafras River. The main residence includes six spacious bedrooms and four and a half baths. The heart of the home is a gourmet kitchen and adjacent generous breakfast room wrapped in 180-degree river views, a setting that enhances every meal. The home flows naturally into multiple large gathering spaces built for entertaining, and into quieter, more intimate rooms designed for reflection and rest. The guest house ensures that you can accommodate family and friends. With three generously sized bedrooms and one and a half baths, full kitchen, fireplace and brick patio, it offers a self-contained retreat that gives guests their own space while keeping everyone together on the estate. The pool complex redefines what a backyard amenity can be. At its center is a 52,000-gallon swimming pool with a retractable electric cover, positioned to frame sweeping panoramic river views. An adjoining heated spa and a oversized pool deck complete a setting that invites long, unhurried afternoons in the sun. Elevating the experience further, it offers a full bath, generous living and dining areas, and amenities more commonly found at a high-end resort - a large, well-equipped gym and an eight-person steam room -providing the perfect end to an active day. Perched at the water's edge, the recently constructed two-story pavilion is the social and recreational heart of the estate's waterfront. It's a front-row seat to everything that makes the Sassafras River so beloved: working crab boats in the early morning, sailboats gliding past at midday, and the sky turning gold over the water at dusk. Spend a lazy afternoon on the pavilion's upper level as the river life unfolds below, then head down to launch your own boat from the private boat lift or boat ramp. The Sassafras and Cox Creek offer boundless activities including boating, water skiing, tubing, wakeboarding, sailing, paddleboarding, and kayaking, all awaiting just steps away. After fun on the water, return to the pavilion for lunch, dinner, or simply a seat with one of the best views on the upper Bay. Adjacent to the grassy wharf, the nearly 1,000-foot private sandy beach is a rare and remarkable amenity ideal for an afternoon stroll with friends or a quiet moment watching the sunset or moon rise over the river. Other improvements along the waterfront include a 1000+ stone revetment protecting the shoreline, a 13,000lb boat lift, and a boat ramp. The grounds reflect a thoughtful balance of beauty, privacy, and long-term stewardship, with carefully planned enhancements designed to complement the natural setting while supporting comfortable estate living. Mature trees and established landscaping create a sense of arrival and continuity across the property, while curated sightlines and open lawn areas transition naturally into wooded edges and surrounding countryside. A network of trails invites exploration through the woods, offering quiet vantage points and seasonal changes that reinforce the property’s connection to the Eastern Shore landscape. The property's blend of fields, woods and waterfront habitats, complemented by offshore hunting rights offers productive hunting. The land supports healthy populations of deer, wild turkey, ducks & geese, creating a sportsman's haven throughout the seasons. Enjoy fishing and crabbing from the dock ideally located on the edge of the deep water channel. Major mid-Atlantic cities, international airports & train stations are within easy reach, making the estate accessible for full-time residents and weekend escapes.

750 Cassidy Wharf Rd, Earleville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$8,950,000
24 Beds ⋅ 13 Baths
Parsons Creek Farm - A 255+/- Acre, Multi-Residence, Deep-Water, Waterfowl & Wildlife Estate at the Confluence of Parsons Creek and the Little Choptank River This once-in-a-lifetime Chesapeake Bay legacy holding is set upon 255.47 extraordinary acres of waterfront, wetlands, upland forest, and meticulously curated wildlife habitat making Parsons Creek Farm one of the most sophisticated private estates on Maryland's Eastern Shore. Masterfully blending historic charm, modern craftsmanship, high-performance land management, and recreational luxury, this turnkey, multi-residence compound stands unrivaled in scale, ecological design, and architectural execution. Positioned at the union of Parsons Creek and the Little Choptank River, the property enjoys nearly a mile of sandy, private shoreline, deep-water access, expansive water vistas, and complete seclusion - yet remains within a short drive to Cambridge, Annapolis, Baltimore, Washington, and the greater Mid-Atlantic corridor. A series of thoughtfully positioned structures - each with its own architectural identity - combine to create a private compound capable of sleeping more than 24 guests in total comfort. Elegantly sited to capture uninterrupted views across impoundments, woodlands, and water, the primary residence blends historic Maryland character with refined luxury. This meticulously designed, 9,583 sq. ft. luxury residence boasts an impressive array of distinct living areas, creating a home of both grand scale and exceptional comfort for family living and entertaining. The expansive property also features a charming, fully renovated, private 1,500 sq. ft. Cape Cod–style guest house that extends a warm welcome to visitors, and a third two-story residence complete with a full bedroom suite, full bathroom, laundry, and sweeping picture windows overlooking one of the ponds. Part of the estate's recreational opportunities is an over-the-water bar and game room, a gathering place where family and friends can cast a line into the pond while enjoying the comforts of a private lounge. Equestrian enthusiasts and entertainers alike will appreciate the impressive stable complex, complete with second-floor luxurious living quarters, a spacious game room, and full bar. Balconies at each end capture sweeping views of the surrounding woodland and water, creating an atmosphere of timeless elegance. Whether envisioned as a generational family compound, a private sporting estate, a conservation-forward investment property, or an exclusive corporate/hospitality retreat, Parsons Creek Farm offers a combination of luxury, ecological engineering, and rural waterfront beauty unmatched anywhere in the Mid-Atlantic. This remarkable waterfront estate is a unique opportunity that unites world-class waterfowl and upland hunting, meticulous wildlife management, and refined living—enhanced by impressive income potential. Having identified his replacement property, the seller is prepared to move forward and welcomes qualified offers.

964 Taylors Island Rd, Madison

Listing courtesy of National Land Realty, LLC. Contact: 4434128971
$8,750,000
5 Beds ⋅ 7 Baths
Commanding extraordinary panoramic Chesapeake Bay views from its south-facing setting, this exceptional waterfront estate offers 210 feet of shoreline on 3.10 private acres in the exclusive Maidstone Farm community. Designed to embrace its remarkable waterfront setting, the residence captures sweeping, unobstructed views from nearly every principal room, with magnificent sunrises, vibrant sunsets, and ever-changing Bay vistas creating a stunning backdrop for everyday living. Enjoy mornings overlooking the water, afternoons boating from your private pier, and evenings entertaining along the shoreline. The protected waters of Burley Creek feature a private pier with 6–7 feet MLW, a 34' x 15' platform, and a 10,000 lb lift, providing effortless access to the Chesapeake Bay. The shoreline offers the perfect launch point for kayaks and paddleboards, while the expansive level lawn creates an exceptional setting for outdoor entertaining and waterfront gatherings. Designed by ABS Architects and custom built in 2019, this exceptional residence blends timeless coastal architecture with sophisticated craftsmanship and modern amenities. The thoughtfully designed floor plan features expansive living spaces filled with natural light, five ensuite bedrooms, 6 full and 1 half baths, four fireplaces including two propane, extensive custom built-ins, and seamless indoor-outdoor living with covered porches and waterside verandas. Architectural details include coffered ceilings, extensive crown molding, 10-foot ceilings on the main level, 9-foot ceilings on the upper and lower levels, 8-foot solid wood doors, 8-inch baseboards, designer lighting, and provisions for a future elevator. The gourmet kitchen is designed for both everyday living and entertaining, featuring two oversized islands, Eucalyptus cabinetry, a La Cornue range, two Sub-Zero refrigerators, Sub-Zero refrigerator drawers, premium hardware, and mitered-edge countertops. The waterfront primary suite offers a private retreat with a barrel vaulted ceiling, sitting area, oversized walk-in closet, and sweeping Bay views. Additional ensuite bedrooms feature custom tile work and refined finishes. A four-car garage with a private flex space above includes a full bath and exercise room, ideal for guests, office, studio, or additional living space. The unfinished 3,664-square-foot lower level provides endless possibilities for future expansion. Additional highlights include a heated saltwater pool overlooking the water, circular driveway, six-zone HVAC, spray foam insulation, 400-amp electrical service, Kohler propane whole-house generator with 2,000-gallon tank, security system, and Control4 audio and lighting automation. Minutes from downtown Annapolis, City Dock, waterfront dining, shopping, and cultural attractions, this extraordinary Chesapeake Bay estate offers a rare opportunity to enjoy a private waterfront lifestyle defined by boating, entertaining, relaxation, and the beauty of the Bay.

2035 Maidstone Farm Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$8,750,000
8 Beds ⋅ 15 Baths
AMAZING OPPORTUNITY TO PURCHASE EXTRAORDINARY PROPERTY AT MAJORLY REDUCED PRICE!! QUALIFIED BUYERS WELCOME! OFFERS WELCOME!!DEAL of a LIFETIME!! "Fine Homes & Lifestyles" cover feature! Architecturally distinguished property. Custom built estate, luxury of modern-day amenities combined with imported, antique, historic, thoughtfully resourced building materials & detail bring centuries old world charm to this extraordinary 10-acre Potomac Tuscany inspired Villa. Minutes to Washington DC. 8 to 12 ensuite bedrooms, libraries, offices, spacious gathering & lecture areas. Land your helicopter-security & privacy; entertain large gatherings-wedding venues, stone chapel replica of ancient Italian estate w/ Della Robbia inspired bell; entertain fine arts displays or performances; host concert pianist recitals; house guests who travel from abroad to attend your venue - closest to downtown Washington DC, convenient location to northern Virginia and Baltimore; minutes to golf courses hosting major tournaments; Airbnb or bed & breakfast hosts' dream property, great place for a spa, relaxing Turkish baths; NIH, medical institution or University satellite location for gatherings to further education, enrichment, group meetings & presentations, international conferences; embassy or consulate ownership, consular offices, ambassadorial residences, government embassy, serene, gated, security & privacy convenient location close proximity to DC; high-level relocation for foreign service officers; relocation consultants, international organizations & consulates; tranquil, inspiring haven to host retreats or ceremonial gatherings; bring your horses; fish-carp filled pond; grow grapes, vineyard potential; artist's inspirational getaway w/studio to display creations; serenity ,writer's escape from hustle & bustle of city ; swim laps year round "against the current" indoor pool (specially designed HVAC system to reduce humidity) enjoy a game of pool volleyball w/ friends; cook in the true gourmet kitchen boasting a spectacular Lacanche stove imported from France; gracious home family, friends & guests can enjoy. Grand property, designed & built w/integrity & genuine craftmanship. Resources, research, history, the study of light and more combined to recreate the appearance of centuries old, Medieval, European influenced architecture and culture & modern comforts for prestigious living, welcome to "Albero del Segnale" Driveway built of centuries old, repurposed cobblestones, came to this country from Europe as ballasts on sailing ships and were then used to pave city streets. Pass through the iron gates, the double stone entrance pillars capped with custom made lanterns from Italy and along the driveway lined with antique streetlamps. Greeted by the front landing made of hand-hewn antique limestone pavers from Italy and twin Corinthian limestone columns also custom made in Italy. Front doors, supported by gold-plated, hand-chiseled hinges custom made in France, spectacular classic Italian design featuring iron grillwork in the glass transoms and a working "man door," door within a door - tradition dates to Medieval times. Grand foyer drenched with natural light from 2+ story windows, welcomed many renown performers and pianists, fantastic acoustics! Every room in this grand, glorious mansion is abundant with natural light, every angle of each room has magnificent windows connecting pastural rolling views with interior. Centuries-old hand-molded antique terra cotta floors w/imprints of the artisan's fingers & hands as well as occasional animal footprints are forever defined - imprinted before the tiles dried and were fired. Solid iron balusters & railings designed for this home &hand forged in Italy & so much more! No HOA offers many potential uses

13320 Signal Tree, Potomac

Listing courtesy of O'Conor, Mooney & Fitzgerald. Contact: (410) 321-8800
$8,750,000
6 Beds ⋅ 6 Baths
Wilderness Estate- REVISED OFFERING INCLUDES 5 PARCELS 6.27.25- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 234 acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look and appreciation for the scope of this offering. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that is the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite. The revised offering of The Wilderness, providing 234 acres comprised of 5 recorded parcels with over 3,000 feet of shoreline is a remarkable opportunity to witness life on the Shore.

27295 Southside Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$8,495,000
6 Beds ⋅ 11 Baths
NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/ over 400’ of direct water frontage is comprised of 3 magnificent structures: a grand main residence, guest cottage, & “party barn” all highlighted by a waterside pool, pier w/ 4’ MLW, pine grove, putting green, extensive landscaping & incomparable craftmanship. The 12,000 SF main residence, positioned to prioritize water views, welcomes you via prominent double lead-glass doors & a grand 3-story foyer w/ dual-staircase. The “river room” w/ 2-story octagon copula offers 270◦ views of the property & creek. The TV room w/ 3 exposures & gas-burning fireplace offers double French doors on two sides leading to the wrap-around flagstone patio. The stunning gourmet kitchen is a true chefs dream. Offering oversized island, built-in media/storage cabinet, coffered ceiling, fireplace, 3 sinks, double Subzero fridges w/ freezer drawers, 2 beverage drawers, 3 dishwashers, Wolf microwave & a stainless-steel Lacanche range with 6-burners, pot warmer, warming oven, & 2 ovens. Complimenting the kitchen is a large walk-in pantry w/ dishwasher, sink & extra freezer in hall. Off the kitchen is a covered porch w/ gas fireplace & “ghost’ screens, a perfect spot to enjoy evenings. A large open dining room has 2 custom built-in display cases. The grand salon w/ bay window, gas-fireplace & intricate mantel is reminiscent of Paris. Adjoining the salon is the handsome 2-story curly cherrywood library w/ custom display cases & leaded-glass pocket doors. The adjoining climate-controlled wine room has a wet bar & storage for 750+ bottles. Wood floors flow throughout the entire main level. The main level is completed by an office, powder room & laundry to service the pool, 2 additional powder rooms, elevator to all 4 levels, mud/dog room, rear spiral staircase, guest suite w/ ensuite bathroom, & 2-car attached garage. The 2nd level offers a generous primary suite w/ fireplace & full length terrace overlooking the water. Her wing features dressing room w/ custom built-ins, separate sitting room, & a luxurious bathroom w/ marble tile, separate shower, jetted tub, & vanity. His wing offers an office w/ fireplace, paneled closet leading to separate bathroom w/ shower, travertine stone, & vanity. From his office access the 2nd level of library, open to below. Just off of the primary suite is a bar area/kitchen. 3 additional bedrooms, each w/ ensuite bathroom, and a laundry room complete the 2nd level. The 3rd level offers theater/rec room, play area, bedroom w/ ensuite bathroom, powder room, & ample storage. The lower-level houses utilities, storage, & enough room for an exercise area. The charming guest cottage sits amongst extensive landscaping. The main level offers a full kitchen, dining area, living room, sunroom, large family room, 2 bedrooms w/ shared bathroom, additional guest bathroom, & large entertaining room. Upstairs is a full bedroom w/ ensuite bathroom. The unfinished lower level offers storage. The party barn originally built for boat storage was designed to look like an old Pennsylvania barn w/ 4’ of stone around the base. Flanked by 2 garage wings allowing for 4+ cars & capped w/ a cupola, the shingled-style barn has two large doors on either side of the building that allow for a trailered boat or 4+ more cars. The 2nd level is a loft w/ sleeping/living area w/ full bathroom, plumbed for potential kitchenette, front & rear terraces, & a spiral staircase to a crow’s nest w/ amazing views. There is a full property generator & a dog run w/ kennel just off the rear. Outside enjoy the benefits of beautiful shore living amongst the verdant grounds, mature landscaping & exceptional views. The pier offers 4’ MLW & the shoreline is fully rip-rapped w/ natural plantings.

8620 Bozman Neavitt, Saint Michaels

Listing courtesy of Washington Fine Properties, LLC. Contact: info@wfp.com
$8,250,000
7 Beds ⋅ 9 Baths
Introducing 8880 Bradley Blvd, a striking contemporary estate set on a fully gated two-acre parcel in one of Bethesda’s most prestigious enclaves. Designed for those who value architectural distinction, privacy, and resort-caliber living, this extraordinary residence offers approximately 13,750 square feet across three levels, with 7 bedrooms, 7 full baths, 2 half baths, and a custom hydraulic elevator serving every floor. From the moment of arrival, the estate makes a commanding impression. An app-controlled arched iron gate opens to a long, scenic approach, culminating in a circular motor court, manicured grounds, and a custom Italian bronze entry door. Inside, the dramatic foyer rises to 24-foot ceilings and is crowned by a sculptural custom light installation by Cameron Design of London, setting the tone for the home’s bold modern aesthetic and refined craftsmanship. Created for both grand entertaining and seamless daily living, the residence showcases expansive interiors, clean architectural lines, sophisticated finishes, and state-of-the-art smart home integration. The main kitchen is appointed with commercial-grade appliances and exceptional workspace, while a separate scullery kitchen with its own entrance provides ideal support for catered events, staff, or effortless everyday functionality. The home’s lower level delivers a true private wellness and entertainment retreat. Thoughtfully designed for leisure at the highest level, it features a Turkish bath with separate warm room and heated marble surfaces, a fully equipped fitness studio, state-of-the-art theater, wine and cigar lounge, and an additional kitchenette with full-size refrigerator, dishwasher, and microwave. Upstairs, the private quarters continue the home’s sense of elevated comfort and calm. The owner’s suite is a sanctuary unto itself, complete with a spa-inspired bath with heated floors, an expansive two-room dressing area, and a serene sitting room with morning bar. Each secondary bedroom is generously scaled and beautifully appointed. The exterior amenities rival those of a luxury resort. Framed by mature trees for exceptional privacy, the outdoor living environment includes a saltwater pool with infinity edge, mosaic-tiled spa, four gas fire pits, and a cabana pavilion with outdoor kitchen, fireplace, and generous entertaining areas. Whether envisioned as a private family compound, ambassadorial residence, or executive retreat, the estate offers a rare combination of grandeur and seclusion. A four-car attached garage with Porsche charging station, basketball hoop, and air conditioning adds further convenience. Throughout the home, remote-controlled window treatments, expansive windows, whole-house soundproofing and insulation, central vacuum, app-controlled surround sound, advanced security, five commercial-grade HVAC systems, two 75-gallon hot water tanks, and generator backup underscore the property’s exceptional infrastructure and readiness. Only minutes from the finest golf, acclaimed schools, upscale shopping, fine dining, and the heart of Washington, D.C., 8880 Bradley Blvd offers a lifestyle that is at once prestigious, private, and profoundly peaceful. Whether serving as a family legacy property, an ambassadorial residence, or a refined executive escape, this remarkable estate captures the essence of modern luxury—where striking design, uncompromising privacy, and the ease of a five-star resort are woven into everyday life.

8880 Bradley Blvd, Bethesda

Listing courtesy of TTR Sothebys International Realty. Contact: (703) 714-9030
$7,995,000
7 Beds ⋅ 9 Baths
Set behind automatic gates on over two landscaped acres in Potomac's Golden Horseshoe, this landmark Bradley Farms estate has undergone a complete transformation by Kent Construction & Development. Built in 1971, the residence has been reimagined from the inside out, preserving its Georgian Colonial proportions while introducing every expectation of contemporary luxury. A sweeping driveway crosses the front lawn to the stately façade, where new Pella windows, restored masonry, and a complementary garage addition bring the exterior forward without disturbing the home's country-estate ethos. The gloss black front door opens to a gracious foyer with checkerboard marble flooring and custom picture frame molding, introducing 14,300 total square feet of exceptional workmanship. Hand-stained solid oak flooring, intricate millwork, solid brass Emtek hardware in polished nickel, and designer fixtures carry a layered design narrative throughout. The main level balances grandeur and livability. The living room spans 35 feet with a roaring fireplace, one of four. Opposite, a dignified library offers a richly outfitted hideaway. A central dining room in a moody dark palette is juxtaposed by the light-filled solarium with flagstone flooring. Structural enhancements open the informal spaces to contemporary demands. At their heart is the bespoke kitchen and adjoining butler's pantry, where custom cabinetry handmade in Italy conceals a suite of Wolf, Sub-Zero, and Miele appliances. Calacatta Fantasy Quartzite clads the center island, farmhouse sink, and slab backsplash, paired with antique brass hardware and Waterworks fixtures. An open breakfast area and family room complete the level, alongside a mudroom accessing the four-car garage, with storage for six vehicles. The grand staircase rises to a primary suite in a dedicated wing. Its spa-inspired bath is clad in Bianco Puro marble, with a marble archway separating dual handcrafted walnut vanities from the freestanding tub and walk-in shower. Custom dressing room cabinetry, imported from Italy, features accent lighting complementing the Acquabelle marble island. Four additional bedroom suites and a laundry room complete the upper level. The top floor opens with a large living space punctuated by dormers in the slate roof. Two bedrooms share a hall bath, and bonus spaces flank either end. A kitchenette and breakfast room suit an in-law suite, au pair quarters, or extended guest stays. The lower level is announced by a custom glass wine cellar, glowing at the entrance to a professional home cinema. Conceived as a private screening room rather than a media space, it is finished with the same rigor as the formal rooms above: custom box molding detailing the walls, automatic Lutron shades, and an integrated Crestron system governing picture, sound, and light from a single control. An adjoining bar completes the experience, as suited to an evening with friends as to a film alone. The remainder is dedicated to wellness: a mirrored fitness room, massage room, sauna, and full bath. Nearly every infrastructure component has been replaced or modernized. Four new HVAC zones, new natural gas service, two 75-gallon water heaters, new electrical infrastructure with a dedicated Pepco transformer, new Comcast service, Lutron lighting automation, indoor and outdoor Sonos audio, integrated security, irrigation, landscape lighting, and renovated pool systems create an estate that performs as impressively as it presents. The fully fenced grounds are equally compelling: expanses of lawn framed by mature trees provide privacy, while the 50-foot lap pool, new stone terraces, extensive lighting, and irrigated landscape suit intimate evenings and large-scale entertaining al fresco. A union of Georgian Colonial architecture, rare craftsmanship, and sophisticated technology, 8901 Durham Drive stands among the finest estate homes along Potomac's Millionaire's Mile.

8901 Durham Dr, Potomac

Listing courtesy of TTR Sotheby's International Realty. Contact:

$7,950,000
7 Beds ⋅ 9 Baths
Presquile Manor House, originally built by the Lloyd Family circa 1800 as one of their three Plantation Houses, sits up high on the Wye River with due West Exposure. The Main House has recently gone through a two-year renovation process from top to bottom by West & Callahan Construction and Peter Zimmerman Architects Inc, with much thought and care to keep all of the historic attributes that this property deserves. The grounds are improved by a pool, tennis court, covered boat house with deep water, formal gardens, magnificent mature trees and a detached 1,670 sq ft caretaker's house. The main parcel is 10.48 acres with an additional 7.1-acre tree lined drive with a perpetual easement. This is a one-of-a-kind property and a true Talbot County piece of History. Furniture is negotiable.

26546 Presquile Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$7,900,000
4 Beds ⋅ 6 Baths
Welcome to this fabulous waterfront estate historically known as The POD. Set behind the gates of an extraordinary 7+ acre waterfront compound, The POD offers a rare blend of privacy, scale, and resort-caliber living along Forked Creek and the Severn River. Beautifully constructed and thoughtfully curated, the property unfolds as a true lifestyle destination, where every detail has been designed to elevate both everyday living and grand entertaining. A long, illuminated drive framed by mature crape myrtles leads to expansive, meticulously landscaped grounds. Outdoor living takes center stage with sweeping wraparound decks, multiple gathering spaces, and a heated saltwater pool surrounded by travertine stone, gazebo, and fire features. An outdoor kitchen, complete with EVO grill, gas burners, refrigeration, and bar seating, creates the perfect setting for waterfront entertaining, while the year-round spa and low-maintenance turf with putting green enhance the ease of ownership. The private pier is a standout, offering multiple slips, lifts, floating dock access, and approximately 10 feet of water depth. An exceptional experience that is ideal for boating enthusiasts seeking effortless access to the Severn River and beyond. Inside, the main residence spans approximately 8,000 square feet, where refined finishes and architectural details are complemented by a light-filled, flowing layout. A grand foyer introduces the home, leading to elegant living and dining spaces, a chef’s kitchen equipped with premium appliances, and a welcoming sunroom overlooking the pool and waterfront. The main level Primary suite with private balcony, fireplace and spa-like bath is the perfect retreat after a day in the pool or on the water. A conveniently located elevator provides seamless access to all 3 levels. Designed for both relaxation and recreation, the lower level transforms into a true entertainment hub, featuring a nightclub-inspired lounge with full bar, a state-of-the-art theater, and dedicated fitness and recreation spaces. Head upstairs where an additional 3 bedrooms, 2 baths and an awe-inspiring office with wrap around deck offer comfort and flexibility for family and guests. A separate guest house offers additional accommodations with its own kitchen, living spaces, 3 bedrooms 2 baths and private comforts, an ideal retreat for extended stays or hosting with ease. Advanced infrastructure and smart home technology, including whole-house automation, security, generator, and climate systems, ensure modern convenience is fully integrated into this exceptional offering. The POD is more than a home, it is a private waterfront retreat designed for those who value space, privacy, and a seamless connection to the water. A truly resort-inspired setting, this property offers an unparalleled opportunity to experience the waterfront lifestyle in its most complete and effortless form. Welcome Home!

423 Benfield Rd, Severna Park

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$7,900,000
8 Beds ⋅ 6 Baths
"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. The adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$7,675,000
5 Beds ⋅ 6 Baths
Sited along the storied Chesapeake Bay, with breathtaking views and beautiful landscaping, this spectacular waterfront Gibson Island property offers the perfect family setting to enjoy the marvels of life along the Bay. The five-bedroom, five and a half bath home sits on a rare double lot, and offers a 63-foot heated lap pool and panoramic views from Bay windows across the entire width of the house. Whether enjoying the mahogany paneled screen porch, the spacious and beautifully designed kitchen, the lovely sun porch or the cozy but richly fashioned library, you will be drawn to the natural setting around you, with lovely morning sun and 180-degree views of the Chesapeake Bay, Bay Bridge and extended Magothy River shoreline. Follow the beautiful hardwood floors throughout the house, including a first-floor bedroom suite with separate entrance. Ascend the elegant staircase to a gorgeous primary bedroom suite and enjoy all its amenities, including a steam bath and gas fireplace. Doors from the primary suite open to outer decks with crafted wooden railings. The second level includes three additional bedrooms, two full baths and a large cedar closet. The family experience extends to the finished basement, containing a pool table, weight and exercise room, and fully equipped sauna. A property of this caliber and scale—offering a lovely, well-cared for home, exceptional Chesapeake Bay waterfront and a double lot—rarely comes to market on Gibson Island. Whether sitting next to the Bayside pool or enjoying the views from the 10 rooms or porches that look out toward the Bay, your family will be surrounded by a natural charm and friendly intimacy befitting the special home that you have chosen. Information on Gibson Island: Gibson Island is a private island within one hour of Washington, D.C. and Baltimore offering an absolutely extraordinary setting. The Island comprises 1000 acres with seven miles of shoreline. Two thirds of the Island is undeveloped and is owned by the Gibson Island Corporation, the homeowners' association. The remaining third is residential home sites. Gibson Island is located on the western shore of Maryland, so there is no need to cross the Bay Bridge. On the Island is a 43-acre spring fed freshwater lake in which one may enjoy non-motorized watercraft activities such as paddleboarding, canoeing, kayaking, fishing and swimming. Gibson Island provides enormous privacy and security--there is an entry gatehouse staffed 24+Hours, and the Island is patrolled by the Gibson Island Police Force (GIPD). The Gibson Island Corporation Service Department offers yard maintenance and landscaping and other services for homeowners. There is a fully equipped yacht yard for boating needs, both power and sail. From the Island, it is just a 20-minute drive to BWI Airport and the neighboring Amtrak train station. The Island houses a private country club (membership by invitation) with a magnificent clubhouse, an award-winning and challenging Charles Blair Macdonald designed 9-hole golf course, swimming, yachting, both power and sail, year-round fine dining, tennis, paddle, pickle ball, summer camp for children, croquet, skeet shooting, and more. (C)

747 Bywater Rd, Gibson Island

Listing courtesy of Gibson Island Real Estate INC. Contact: 4102551341
$7,500,000
4 Beds ⋅ 3 Baths
Nestled within the prestigious St. Jeromes subdivision, this exquisite Bayfront residence offers an unparalleled lifestyle defined by luxury and tranquility. Spanning over 175 acres just with the main house, this coastal architectural masterpiece seamlessly blends sophisticated design with nature's beauty, providing a serene retreat for discerning homeowners. Step inside to discover a harmonious open floor plan adorned with rich hardwood. The expansive family room, complete with a cozy wood-burning fireplace and elegant mantel, invites relaxation and gatherings. The kitchen is a culinary enthusiast's dream, featuring an island, ample pantry space, and an inviting eat-in area. The primary suite is a sanctuary of comfort, boasting a Bayfront view, and a luxurious primary bath equipped with a walk-in shower. Additional highlights include built-ins, recessed lighting, and a dedicated entry-level bedroom, ensuring convenience and style throughout. The exterior of this residence is equally impressive, showcasing extensive hardscaping that enhances the property's aesthetic appeal. Enjoy the ultimate outdoor lifestyle with a private beach, perfect for sunbathing or leisurely strolls along the sandy shore. The roof deck offers panoramic views of the Chesapeake Bay, while the tennis court (should you choose to restore it) provides an active lifestyle option right at your doorstep. Multiple patios and decks create inviting spaces for al fresco dining and entertaining, all set against a backdrop of lush greenery and serene Chesapeake Bay views. This premium lot is a true gem, bordered by trees and offering a secluded atmosphere that feels worlds away from the hustle and bustle. With direct access to the Bay, indulge in fishing, boating, or simply soaking in the natural beauty that surrounds you. Ample parking with an attached garage and expansive driveway. Breathtaking views of the Bay, pond, and wooded areas create a picturesque setting that changes with the seasons. Located just steps from the water's edge, this home offers a unique opportunity to embrace a lifestyle centered around nature and luxury. With over 6,136 feet of water-frontage, this property provides direct access to the Chesapeake Bay, where swimming, kayaking, and water skiing await. This exceptional residence is not just a home; it's a lifestyle choice that embodies luxury, comfort, and the beauty of nature. Experience the ultimate in coastal living, where every day feels like a vacation. Sale includes 91 lots in St. Jeromes shores and 71 lots in Bay Harbor totaling approximately 280 acres. There is nothing else like this in Southern Maryland. Your legacy awaits.

50645 Holly Point Rd, Dameron

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169
$7,500,000
6 Beds ⋅ 8 Baths
Tucked away at the end of a quiet, private cul-de-sac in one of Potomac’s most sought-after neighborhoods sits something truly special: 2.6 acres of pure possibility. This is your chance to build a stunning contemporary residence of roughly 13,000 square feet that feels more like a private resort than a home. Imagine a beautifully designed estate with six bedrooms and nine bathrooms, anchored by an incredible primary suite complete with a spacious lounge area, a fireplace, massive closets, and a spa-like bathroom you’ll never want to leave. The rest of the house is just as thoughtful; there’s a dedicated office, a library, exquisite stone and woodwork throughout, and every smart-home feature you could possibly want. Outside, the fun really begins. You’ve got a cabana with a full outdoor kitchen, cascading waterfalls feeding into the pool, your own basketball/pickleball sport court, a private putting green, and plenty of inviting spots to gather with friends and family. There are organic gardens if you love to grow things, and we’ve even included space for a fantastic indoor spa so you can unwind year-round, no matter the weather. Picture this: hosting a lively ping-pong tournament on the sport court, practicing your short game on the putting green at golden hour, or gathering everyone around the fire pit with music flowing through the surround-sound system. With parking for up to ten cars, you can easily bring in a house full of guests. And when the party’s over, slip away to your home office or gym, then end the night soaking in the tub of your spa-inspired primary bath while enjoying those serene pool views. Every last detail here can be customized exactly the way you want it. This is more than just a luxury home; it’s your personal escape, where sophistication meets total tranquility. Ready to make it yours?

9933 Bentcross Dr, Potomac

Listing courtesy of TTR Sotheby's International Realty. Contact: 3015161212
$7,500,000
5 Beds ⋅ 7 Baths
This Severn River estate is a rare opportunity to own one of the area’s most spectacular properties. Showcasing a negative-edge pool with beach entry and hot tub, 2 private piers to accommodate a variety of vessel sizes including a 100 ft slip, sprawling yard and sweeping views of the river and Naval Academy Bridge. Imagine waking each morning to the sun sparkling off the Severn, its reflection dancing across the water and spilling into a home designed to embrace the view at every turn. This extraordinary residence is both a private retreat and an entertainer’s dream, with expansive balconies and roof decks on every level, making indoor/outdoor living a breeze. Inside, soaring ceilings and walls of glass frame the ever-changing views like a living masterpiece, while the grand chef’s kitchen, stone-floored sunroom, and elegant dining spaces invite gatherings large and small. The primary suite is an entire level of indulgence, complete with soaring ceilings, a fireplace, spa-like bath, wet bar, expansive dressing room, laundry, and its own private balcony for starlit evenings. Additional ensuite bedrooms and a guest suite with kitchenette ensure comfort for family and friends, while the lower level—with wine cellar, kitchenette, and direct access to the pool—extends the living space to the outdoors. With a sandy beach and two private piers, one tucked into Crouches Cove and the other stretching into the Severn river, this estate offers not just a home but a lifestyle of breathtaking vistas on the water, boating adventures at your doorstep, and the unmatched beauty of Annapolis waterfront living. Located in the Blue-Ribbon Broadneck School district and just 5 miles to downtown Annapolis, convenient to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., the location provides the very best this region has to offer in a 30-mile radius. If you are looking for a truly special property with EPIC water views, resort like amenities and a great private setting, this is the property you have been waiting for. Welcome Home!

125 S Winchester Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$7,500,000
6 Beds ⋅ 8 Baths
Set along the peaceful waters of Caulk Cove, this extraordinary waterfront estate offers luxury, privacy and natural beauty across more than 10 acres. The property features open farm fields and professionally landscaped, park-like grounds, with a tree-lined driveway creating a breathtaking approach to the residence. Built in 2013, the custom-designed home encompasses nearly 8,500 square feet of thoughtfully curated living space, positioned to capture sweeping waterfront views. A gracious front porch welcomes you into a grand foyer, setting the tone for the exceptional craftsmanship found throughout. The main level offers soaring 12-foot ceilings, rich hardwood floors, expansive windows and doors and custom millwork including crown molding, coffered and tray ceilings and elegant board-and-batten detailing. At the heart of the home, the living room serves as a remarkable gathering space with a dramatic floor-to-ceiling stone fireplace, custom built-ins, coffered ceilings, a wet bar and access to the rear porch. The kitchen is a stunning focal point, featuring a diamond coffered ceiling, custom handmade walnut cabinetry, two oversized islands, white and leathered granite countertops, and a Wolf six-burner, dual-oven range. A fully equipped butler’s pantry offers extensive cabinetry, generous counter space, a secondary refrigerator, dual dishwashers, a wine refrigerator and an electric oven. The open dining area flows seamlessly between the kitchen and living room. The primary suite is a private retreat with a tray ceiling, wood-burning fireplace, expansive walk-in closet with custom built-ins and vanity and a luxurious bath featuring heated floors, a jetted soaking tub, separate vanities, an open tile-and-glass shower and a private water closet. The suite is completed by a private sitting room with fireplace and wet bar, along with a private screened porch overlooking the gardens and serene waterfront. Four additional ensuite bedrooms each offer unique and luxurious bath designs. A well-appointed laundry room with ample cabinetry and generous counter space enhances everyday convenience and leads directly to a functional mudroom with access to the attached two-car garage. The second level features 9-foot ceilings and is anchored by a spacious family room with a stone hearth wood-burning fireplace and built-in window seating, flowing into a billiards area with wet bar, creating an ideal space for entertaining. The sixth bedroom currently includes custom built-in bunk beds but was originally designed as a home office and offers flexibility to be restored to its original use. The home’s exceptional design extends seamlessly outdoors, with a spacious screened porch leading to an open-air porch with a wood-burning fireplace and outdoor entertainment setup. Bluestone walkways and patios lead to a 20’ x 40’ lagoon-style Gunite pool with a waterfall feature, an outdoor kitchen and a waterside fire pit offering stunning sunset views over the cove. The property also includes a charming one-bedroom guest house with a luxury kitchen, open living area with fireplace and screened porch. A private dock with approximately 6’ MLW offers two boat slips, a floating dock and access to waterfront dining and premier fishing throughout the Chesapeake Bay and surrounding tributaries. Additional highlights to the home include a greenhouse with raised garden beds, a fenced garden area, professional landscaping with accent lighting, and a full irrigation system. This exceptional estate is truly one-of-a-kind!

7508 Cooper Point Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$7,250,000
4 Beds ⋅ 4 Baths
Perfectly positioned along the waterfront in the prestigious Murray Hill neighborhood of Annapolis, this extraordinary estate represents a rare opportunity to own a fully reimagined luxury residence where privacy, walkability, boating lifestyle, and architectural sophistication converge in one of the East Coast’s most coveted waterfront settings. RenownedBohan Contracting has been extensively renovating the home since October 2025. The home has not been lived in since completion, offering an exceptionally rare “like-new” experience where every finish, appliance, system, and curated detail remains untouched. Set on an unusually expansive waterfront lot for downtown Annapolis standards, the property delivers a sense of scale and privacy that is nearly impossible to replicate within Murray Hill. Mature landscaping, multiple outdoor living spaces, Brazilian Ipe decking, and panoramic water views create a setting that feels worlds away while remaining just moments from the energy and charm of downtown Annapolis. Designed for the discerning buyer seeking a refined waterfront retreat, the residence effortlessly balances elevated entertaining with relaxed coastal living. Whether arriving by boat after a day on the Chesapeake Bay, hosting sunset gatherings overlooking Spa Creek, or enjoying peaceful mornings watching sailboats drift by, the home was designed around an experience. Inside, timeless design and modern luxury unfold at every turn. The fully reimagined chef’s kitchen rivals those found in premier custom estates, anchored by a complete JennAir Noir appliance suite including a 48-inch dual-fuel range with double ovens, professional refrigeration, dual integrated dishwashers, multiple beverage centers, built-in ice maker, and a butler's pantry designed as both a prep and entertaining space. Custom Schrock “Trademark” maple cabinetry, designer-selected Waterworks fixtures, Calacatta Miraggio Cielo quartz with dramatic waterfall detailing, and layered architectural lighting elevate the space into a true showpiece. Throughout the residence, every finish was intentionally selected to create warmth, sophistication, and understated luxury. Wide-plank white oak flooring, custom white oak ceiling beams, Restoration Hardware lighting, Baldwin hardware, integrated Sonos audio throughout the home, Lutron lighting controls, custom plaster fireplaces, upgraded insulation for sound attenuation, and CAT6 wiring provide the seamless blend of craftsmanship and modern infrastructure expected at this caliber of home. The primary suite serves as a private sanctuary, complete with custom built-ins, boutique-style California Closets systems, integrated laundry, and a bespoke fireplace designed to create an atmosphere reminiscent of a luxury waterfront hotel suite. Every secondary space continues the same level of thoughtful execution and design continuity rarely achieved in residential renovations. Outside, the waterfront experience becomes truly exceptional. A private pier with electric, boat lift, paver stone extended driveway, refinished gates, and oversized outdoor entertaining areas creates a lifestyle tailored for effortless luxury. The property’s unique positioning offers both protected water access and breathtaking views while maintaining an uncommon sense of seclusion in the heart of Annapolis. Located just minutes from Downtown Annapolis, the United States Naval Academy, award-winning restaurants, yacht clubs, boutique shopping, and private aviation access, this home is ideally suited for the executive or entrepreneur seeking an uncompromising second home or primary waterfront residence within easy reach of Washington D.C., Northern Virginia, Philadelphia, and New York. The ability to enjoy a true luxury waterfront lifestyle with boating access, walkability, privacy, and substantial land all within one of Annapolis’ most prestigious neighborhoods is extraordinarily rare.

11 S Acton Pl, Annapolis

Listing courtesy of Real Broker, LLC - Severna Park. Contact: 8445517325
$6,995,000
4 Beds ⋅ 6 Baths
Set on a spectacular point of land where the South River meets the Chesapeake Bay, this extraordinary waterfront estate captures some of the most breathtaking views in Annapolis. With coveted southern exposure, the property is immersed in sunlight from dawn to dusk, creating an ever-changing backdrop of sparkling water, passing sailboats, and panoramic Chesapeake vistas. Completely reimagined in 2017 by renowned architect Cathy Purple Cherry, this residence was rebuilt and renovated to an exceptional standard, blending timeless coastal architecture with modern luxury and uncompromising construction quality. Spray-foam insulated walls and roof, steel reinforcement, double plywood construction, four-zone HVAC with humidifiers, gas backup heat, tankless propane water heaters, water treatment systems, generator backup, Sonos audio, and Lutron lighting create a home that is as efficient and functional as it is beautiful. Designed for both grand-scale entertaining and comfortable everyday living, the interior offers over-the-top craftsmanship and thoughtful details throughout. Maple hardwood flooring flows through elegant yet inviting spaces including a dramatic waterfront living room with a custom wet bar, an informal gathering room with built-in bookshelves, a private office with custom cabinetry, wet bar, balcony, and commanding views stretching down the Chesapeake Bay, and a state-of-the-art theater room complete with its own wet bar, refrigerator, and ice maker. The chef’s kitchen is a masterpiece featuring double Wolf ovens, Wolf cooktop, Sub-Zero refrigerator, three dishwashers, wine cooler, ice maker, built-in microwave, instant hot water, walk-in pantry with custom built-ins, and a sun-filled breakfast nook overlooking the water. The luxurious primary suite serves as a private waterfront retreat, highlighted by a stunning spa bath finished with Italian water-cut marble. Three additional bedrooms feature ensuite baths, while a full bath on the main level conveniently serves the pool and outdoor entertaining areas. Outdoor living rivals the finest resorts. Expansive Ipe decking surrounds a heated PebbleTec pool and spa, complemented by an outdoor kitchen, fire pit, integrated sound system, and extensive landscape lighting. The private pier is equipped with water, electric, approximately 4 feet of MLW, a 12,000-pound boat lift, an 8,500-pound boat lift, and a 1,500-pound personal watercraft lift, providing immediate access to the Chesapeake Bay and beyond. Offering 4 bedrooms, 5 full baths, 1 half bath, a dedicated office, and a deep four-car garage, this is a rare opportunity to own one of Annapolis’ premier waterfront properties in a setting where extraordinary architecture, unmatched craftsmanship, and world-class outdoor living come together on the shores of the Chesapeake.

3728 Ramsgate Dr, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$6,995,000
7 Beds ⋅ 6 Baths
Escape to another world with this striking French modern waterfront estate. Exquisitely sited on a premium and private 4.15 acre lot with 600 feet of impressively rip-rapped water frontage, coveted waterfront pool, tennis court and picturesque views of the serene waters of Whitehall Creek. This ultra-luxe 9,000+ square-foot, 7 bedroom, 5.5 bathroom custom built home has been completely renovated. It is evident from the moment you walk in the front door that no expense was spared with this stunning home. Curated with premium quality, top of the line materials, combined with the tranquil views, exquisite design, and top-tier finishes, 1524 Cedar Lane Farm Road is truly one-of-a-kind and showcases unparalleled craftsmanship. The property both inside and out is an absolute entertainer's dream. The lush lawn and landscaping gracefully extends to the water's edge and leads to the well-appointed multi-slip IPE pier with boat lifts, 2 jet ski lifts, upgraded power, water and great lighting including underwater LED fishing lights. Inside, this stunning home boasts an awe-inspiring Great Room with soaring ceilings, architectural beams, and panoramic water views and features brushed Teak hardwood flooring, renovated high-end gourmet Kitchen with marble counters, 10 burner Wolf range, 5 fireplaces, Restoration Hardware lighting, renovated bathrooms throughout and much more! Fall asleep to captivating, sweeping views from the Primary's suite, enjoy watching the early morning wildlife activity on the water. Located on Whitehall Creek which flows out to Whitehall Bay and beyond to the Chesapeake Bay, you are perfectly located to take advantage of the Bay's best cruising and fishing areas. Attractive destinations such as the Annapolis Harbor, Baltimore's Inner Harbor, St. Michaels, Oxford, and Solomon's Island are only a short cruise away and just minutes from accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!

1524 Cedar Lane Farm Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$6,975,000
4 Beds ⋅ 4 Baths
NEW AND IMPROVED PRICE - now offered at $6,975,000! Stoney Springs Farm is unique, recreational, and extraordinary - 315+/- acres crafted for collectors, hunters, equestrians, and agritourism visionaries alike. Just 30 miles from Washington, DC, the property commands breathtaking panoramic views stretching from Sugarloaf Mountain to downtown Bethesda. The anchor of the property is a masterfully BOWA-built, timber-framed bank barn. Spanning 8,200 square feet on three secure and climate-controlled levels, it features Douglas Fir beams and flooring, commercial-grade capability including a chain hoist and hydraulic lift, a full kitchen with high-end appliances, 1.5 baths, and the infrastructure to showcase and care for a collection of up to 20 exotic cars. This estate also caters to the huntsman, offering mature woods, open fields, and strategically placed stands and food plots creating exceptional habitat and trophy opportunities. The custom built, 4-bedroom, 3.5 bath colonial farmhouse is comprised of 4,800 finished square feet and features a coveted main level primary bedroom suite, a country kitchen with top-of-line appliances, gorgeous reclaimed oak floors, custom millwork, an oversized and versatile upper bonus room with rear staircase, inviting front and rear covered porches offering tranquil vista and spectacular sunsets, and is equipped with Geothermal HVAC. Completing the property is a detached three-car garage with workroom and covered porch, and a substantial and functional four-bay agricultural shed. There are two high-producing wells, multiple productive crop fields and cultivable land, and it is perc approved for an additional 6-bedroom house. Nationally acclaimed magnet Poolesville High School cluster and the quaint Town of Poolesville are located less than three miles away. As one of the largest private estates in western Montgomery County, Stoney Springs offers unmatched versatility and a rare opportunity to invest in an irreplaceable landscape, shape a lasting legacy, and bring your vision to life! NOTE: There is no sign on property - please do not walk or drive on property without permission from listing agent. Cross reference MLS #MDMC2156274

21100 W Offutt Rd, Poolesville

Listing courtesy of TTR Sotheby's International Realty. Contact: chevychase@ttrsir.com
$6,800,000
5 Beds ⋅ 6 Baths
Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design. The custom brick exterior is crowned by a new cedar shake roof with copper caps and bands, creating a refined profile that blends seamlessly into the natural surroundings. Double mahogany doors with full-view, artistically designed leaded glass open to a luminous foyer with immediate, breathtaking views of the water. Inside, riff-sawn red oak floors flow through expansive formal and informal living areas. Vaulted ceilings add architectural drama, while curated lighting provides warmth and sophistication throughout. The main level features formal living and dining rooms, a stunning gourmet kitchen, and multiple spaces designed for both relaxation and entertaining. The kitchen is a chef’s dream—equipped with top-tier appliances, a large center island, sitting area with fireplace, and an eat-in dining space. Just off the kitchen, a beautifully crafted screened porch with an octagonal ceiling offers a peaceful, year-round retreat. A walk-in pantry and custom-designed bar enhance both function and hospitality. Also on the main level is a striking private office wrapped in Anigre wood paneling, featuring custom built-ins and a circular backlit ceiling. A separate guest wing includes a spacious family/recreation room with spectacular river views and two guest suites with ensuite baths. The primary suite enjoys its own private wing, with serene water views, a cozy sitting area and fireplace, dual walk-in closets, and an elegant dressing hall. The luxurious, spa-inspired bath includes a soaking tub and glass-enclosed shower, creating a true sanctuary of comfort and privacy. Upstairs, dual wings on opposite sides of the home offer two additional guest suites with ensuite baths, a bonus/music room, and a dedicated fitness room. Five fireplaces handcrafted by Collecio Brothers Stone Masons bring warmth and timeless character throughout the home. Modern systems include geothermal heating and cooling, a new Honeywell HVAC control system, Vantage lighting automation, a fully encapsulated crawlspace, and a Generac generator. In addition to the oversized 3+ car attached garage, a separate detached two-bay garage offers equipment storage, a workshop, and a half bath. Outdoors, the estate is designed for both grand entertaining and quiet waterfront living. Features include an extended waterside patio, beautiful pool house with a fully equipped outdoor kitchen, two dressing rooms, an outdoor shower, and an in-ground pool with heated spa. Over 1,000 feet of riprapped shoreline and a 210-foot private dock with two slips, a floating dock, and 7-foot MLW offer direct access to the Chesapeake Bay. This remarkable estate was built for luxurious living, effortless entertaining, and a deep connection to the natural beauty of Maryland’s Eastern Shore. *Current taxes are based on homestead credit.

7090 Cooper Point Rd, Bozman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$6,500,000
7 Beds ⋅ 9 Baths
Tucked away behind the nationally-renowned Congressional Country Club, its namesake Country Club Drive is one of Bethesda’s most prestigious streets, with a mere 26 of the very finest estate homes dotted along sweeping curves in a picturesque setting. Within this rarified air, at the apex of a verdant cul-de-sac, is this quintessential colonial estate home. Tucked away far back from the street, its elegant approach is via an elegant circular driveway, revealing a white brick facade capped by a cedar shake roof evoking cues of classic old-world New England colonials situated on large swaths of land, and exuding an ethos of quiet luxury. Contrasting black shutters infuse the classic exterior with a modicum of modernity as one approaches the central front door via flagstone walkway. The blend of tradition and currency is further carried through the interiors, which have been comprehensively reimagined to suit the tastes of a contemporary luxury clientele while retaining its quintessential elegance. A traditional center hall foyer is flanked by embassy sized formal living and dining rooms. The former can be discreetly closed off via pocket doors, enjoying an ethereal palette augmented by natural light flooding in from the Palladian window on its far side, illuminating the roaring fireplace wall flanked by custom built-ins. The latter also showcases a fireplace, one of five in the home, this one featuring a bold, dark marble surround to complement the moody, sophisticated palette à la fine dining establishment – for sophisticated large scale entertaining. A transverse gallery bifurcates the main level’s formal and informal spaces, with the large family room and its wall of glass, rustic floor-to-ceiling stone fireplace wall, and patio access serving as a midpoint. The chef’s kitchen is the heart of the informal wing. Enjoying almost a European-level of minimalism, its white shaker cabinetry and matching counters conceal a comprehensive suite of state-of-the-art appliances, and are contrasted by a dark, full-height backsplash wall. A large family entrance and mudroom, additional powder room, connection to the butler’s pantry, and direct access to the oversized three-car garage are conveniently tucked away in this wing. A private library with built-ins connected to a spacious den surrounded by glass, both with coffered ceilings, completes the main level. A transverse hallway on the upper level commences at the top of the sweeping staircase and mirrors that of the gallery below. The exquisite primary suite spans the entire width of the upper level, with a large bedroom overlooking the lush grounds. The central dressing room is akin to a luxury boutique in scale and layout, with multiple nooks all surrounded by extensive illuminated built-ins. Minimalist yet still lavish, the primary bath boasts the ubiquitous double vanity, freestanding soaking tub, separate water closet, and walk-in shower. Three additional generously proportioned bedrooms, each with a designer ensuite bath, complete the upper level alongside a spacious and conveniently located laundry room. A finished third level comprises two additional private bedroom suites, ideal for young adults, a fitness studio, bonus space, or a fully private telecommuting solution, as well as ample storage space. A comprehensive entertainment zone, the lower level revolves around a substantial recreation room which spans over 47 feet in length. A professional home cinema is found at one end, while a large fitness center and step-down game room, currently set up as a golf simulator, are found at the other. A spa-inspired bath including a full sauna completes the space. The home’s outdoor space is another certain highlight, occupying 2.06 coveted acres in a proximate Bethesda location. The manicured landscaping is complemented by a flagstone patio, comprising a pergola above a modern linear fire pit, full outdoor kitchen, and sunken hot tub.

8611 Country Club Dr, Bethesda

Listing courtesy of TTR Sotheby's International Realty. Contact:

$6,500,000
7 Beds ⋅ 9 Baths
A truly iconic Annapolis offering, this extraordinarily rare waterfront estate is gracefully set on 7.5 remarkably private acres, showcasing what may be the most breathtaking panoramic views in all of Annapolis. With endless, horizon-stretching vistas that evoke the feel of an oceanfront retreat, the Chesapeake Bay unfolds before you with the Bay Bridge creating a dramatic backdrop in the distance, while Annapolis’ beloved summer sailboat races become part of your everyday scenery. A setting of this magnitude—offering serenity, privacy, and commanding water views—is simply irreplaceable. Encompassing more than 9,000 square feet, this grand residence was thoughtfully designed to maximize its extraordinary setting, with jaw-dropping water views greeting you the moment you step through the front door and drawing your eye through the soaring two-story family room straight to the Chesapeake beyond. The architectural footprint and flow are exceptional, creating the perfect canvas for a visionary buyer to elevate this estate into a world-class showpiece. The main level is anchored by an expansive waterfront primary retreat, a sanctuary unto itself featuring dual walk-in closets, a spa-inspired bath with a jetted soaking tub, oversized skylit shower, separate vanities, a bidet, and a private spiral staircase leading directly to the lower-level fitness and hot tub retreat. Two additional generously sized en suite bedrooms with walk-in closets are also conveniently located on the main level, along with a richly appointed study/library, elegant formal dining room, spacious kitchen with island and breakfast area, plus an additional family gathering space designed for effortless everyday living and entertaining. Upstairs, two exceptional en suite bedrooms each offer walk-in closets, fireplaces, private waterfront balconies, and spectacular elevated views that feel suspended above the Bay. The walkout lower level is equally impressive, designed for entertaining and multigenerational flexibility, featuring expansive recreation spaces opening directly to the waterfront patio, plus a fully self-contained in-law or au pair apartment complete with its own kitchen, family room, full bath, separate entrance, and—of course—those same extraordinary views. What sets this offering even further apart is the remarkable future potential already in motion. With public sewer and an extraordinary 7.5-acre footprint, the possibilities are nearly limitless. Seller-approved county plans—transferable to the next owner—dramatically accelerate the vision, including plans for shoreline improvements, tree clearing to further expand views, bank reshaping, revetment enhancements, a new tram and stair access to the pier, a widened driveway with a new entrance feature, a detached guest house with its own private entrance from Lyons Dr, a pickleball court, a gazebo, and additional grounds enhancements. This is more than a home—it is one of Annapolis’ most extraordinary legacy properties, offering a once-in-a-generation opportunity to create an unparalleled waterfront masterpiece.

2562 Carrollton Rd, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$6,500,000
4 Beds ⋅ 8 Baths
Live authentically. Blissfield… A vision realized. Set upon 54 acres in the heart of Maryland’s legendary horse country. Blissfield is a dazzling architectural masterpiece. Born of a resolute appreciation of form, scale and intrinsic quality, the entire estate bespeaks reverence for bold vision, artistic creativity, and thoughtful collaboration among different disciplines, which has produced a property of undeniable elan. A creation of indisputable beauty befitting the glorious grounds upon which it sits, Blissfield is both a sanctuary and a triumph. A tree-lined drive leads you to the reveal of an epic glistening pond with an authentic English Manor estate perched just so. Impeccable finishes abound in both the exterior and interiors. Exterior walls, built of Gettysburg Stone. Custom limestone sills and entrance. Copper standing seam roof, gutters, downspouts, and flashing. Custom, hand-forged iron railings, balcony, gates, and hardware. Hand-crafted cabinetry and paneling of wormy chestnut, vintage pine, satinwood, cherry, English oak and pecan. Flooring of vintage oak, pine, and quarter-sawn travertine marble. Eight Rumford-style fireplaces. Heated flooring. Field-built trusses of vintage hand-hewn beams. Antique marble mantles. Antique French bronze chandeliers. Satinwood lady’s dressing room and distinguished gentleman’s dressing room. Hardscapes of Belgian block and bluestone. Every room has been designed to reflect a human scale, and to take advantage of glorious vistas. The estate includes light-filled wings, french doors, and casement windows that allow one to connect to the many gardens and terraces. The home includes four-bedroom suites, eight bathrooms, family room, sun room, great room, library, dining room, eat-in kitchen, morning room, two master dressing rooms, mud room with kennels, and elevator. English club-style lower level with wine room, billiards room, and bar. Private office in main house. The grounds and the home have been designed to complement and take advantage of the stunning views across a two-acre, 12 foot deep, spring-fed, stocked pond. The outbuildings include: a potting shed, equipment shed, and pool pavilion, all with copper roofs. Bank barn, c.1860 with stable with tack room, stalls, and wash-down. Dairy barn, including a second floor apartment with two bedrooms, baths, and a full kitchen, wainscoting, heat, A/C, and fireplace. A guest home with three bedrooms, three full baths, fireplace is also on the grounds. (Barn and other structures currently generate strong rental income.) In-ground heated swimming pool. Twenty acres of fenced paddocks, with run-in sheds and automatic waterer. Two streams and one bridge. Formal English gardens. In-ground automatic sprinkler system. Generator, four generous wells, and natural gas. Stately and eminently livable, Blissfield beckons. Convenient access to Baltimore and Washington, D.C. One of America’s finest estates. Cultivate your existence. The art of uniting human and home. Architect: Robert Hollendonner | Interiors: LeVanis Associates, Inc. | Landscape Architect: Stratton Semmes, Annapolis | Builder: GYC Group, Ltd. | Date completed: 1999.

14921 Old York Rd, Phoenix

Listing courtesy of Krauss Real Property Brokerage. Contact: (410) 804-7921
$6,499,900
7 Beds ⋅ 9 Baths
Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with a sprawling island, Wolf range, and access to a four-season room that opens fully to the outdoors through custom bi-fold doors. The main-level primary suite spans nearly 900 sq ft with a private balcony, soaking tub, his-and-her vanities, and a massive walk-in closet. Enjoy five fireplaces, an indoor pool with fountains and a full bath, and three levels of outdoor living, including an outdoor kitchen, built-in hot tub with gazebo, outdoor shower, and deck drainage system to keep lower levels dry. Entertain with ease in the rec room with an industrial-style bar, climate-controlled wine cellar, and fully equipped gym. Three attached garages connect to a locker-style mudroom, with a lower-level garage ideal for a side-by-side or lake toys. Radiant heat, a whole-house generator, and three dock slips make this property as functional as it is flawless. A rare opportunity to own a true statement home in one of Deep Creek Lake’s most prestigious communities. Call today for your private tour!

47 Holy Cross, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$6,495,000
4 Beds ⋅ 5 Baths
Irish Creek Waterfront Estate Set along more than 1,000 +/- feet of pristine, navigable waterfront on Irish Creek, this remarkable 22.14 +/- acre waterfront estate captures the very essence of luxury living on Maryland’s Eastern Shore. Surrounded by sweeping southwest-facing water views and unspoiled natural beauty, the property offers exceptional privacy and scale just minutes from the charming towns of Easton and St. Michaels. Approached by a long, private paved drive, the stately Colonial residence blends timeless architecture with comfortable sophistication, designed for both elegant entertaining and relaxed waterfront living. Inside, refined interiors feature rich hardwood flooring, extensive crown molding, custom built-ins, and four wood-burning fireplaces, creating warm gathering spaces throughout the home. The main level is thoughtfully designed for hosting and everyday living, with gracious formal and informal spaces that flow effortlessly together. A formal dining room, expansive living and family rooms, and a well-appointed kitchen with island and pantry create the perfect setting for gatherings with family and friends. The main-level primary suite offers a peaceful retreat with its own fireplace, walk-in closet, and spa-inspired bath. Upstairs, three additional bedrooms and two full baths comfortably accommodate guests for extended weekends on the Shore. Outdoors, the estate unfolds as a private waterfront retreat designed for unforgettable weekends and celebrations. Spend warm summer days by the Gunite pool and outdoor spa, gather around the built-in fire pit at sunset, or enjoy a friendly match on the bocce court. A tranquil pond and expansive grounds enhance the sense of serenity, while the vaulted three-season porch provides the perfect vantage point for watching boats drift by and taking in the breathtaking evening sunsets over Irish Creek. The property is exceptionally well-suited for hosting, with a charming pool house and a separate two-bedroom guest apartment above the detached four-car side-entry garage—ideal for visiting family, weekend guests, or extended stays. Located in the coveted Royal Oak waterfront community, and within easy reach of Easton, St. Michaels, and the Chesapeake Bay, this extraordinary offering is less than two hours from Washington, D.C., Baltimore, and Philadelphia, making it the perfect luxury retreat for weekend escapes or year-round living on the Eastern Shore. Here, life slows down—boating at sunset, long summer weekends with family and friends, and the timeless beauty of Chesapeake Bay living.

24679 Deep Neck Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$6,375,000
2 Beds ⋅ 3 Baths
Duvall Farm is a rare Eastern Shore offering — a 408± acre farm that blends meaningful conservation efforts with immense easement potential, productive farmland, and refined residential improvements in a location between Easton and Oxford. Significant in both scale and character, the farm is comprised of 20 recorded parcels, presenting long-term value and a wide range of opportunities. The land itself is remarkable. With significant acreage enrolled in the Conservation Reserve Program, over 185± acres provide restored habitat for wildlife and waterfowl. Another 50± acres remain under active cultivation, sustaining the farm’s agricultural heritage. The balance of the property presents a diverse mix of wetlands, mature woodland, wooded buffers, upland habitat, and scenic fields. These varied landscapes support habitat restoration and sporting use, while offering beautiful vistas in every season. A carefully maintained network of trails, and farm lanes provide access throughout the property, making it well-suited for recreation, hunting, and conservation management. At the heart of Duvall Farm is Duvall Lodge, constructed in 2006 by Ilex Construction. Drawing inspiration from Tennessee Pioneer architecture, the lodge is both timeless and inviting. The design embraces rustic authenticity while incorporating every modern comfort. Inside, the great room makes a dramatic impression with soaring ceilings, reclaimed timbers, wide-plank wood floors, and a massive stone fireplace that anchors the space. Exposed beams and natural materials create a warm ambiance, while broad windows and doors seamlessly connect the interior to the surrounding landscape. One of the lodge’s defining features is its full wraparound screened porch, offering sweeping views over a tranquil pond, stocked with bass and with a small pier. Whether for quiet mornings or gatherings with friends, the porch underscores the property’s seamless blend of indoor and outdoor living. Nearby, a hand-hewn log guest cabin extends the accommodations, creating a setting well suited to hosting family and friends. The improvements are understated yet thoughtful, designed to complement rather than dominate the landscape. They reflect the same stewardship evident across the farm itself — an approach that values authenticity, conservation, and the enduring character of the land. Duvall Farm is more than acreage; it is a complete environment, where agricultural productivity, habitat diversity, and architectural charm intersect. Few properties on Maryland’s Eastern Shore offer this combination of size, recorded parcels, conservation value, and a central lodge that feels historic with modern amenities. The location, just minutes from Easton and Oxford, places Duvall Farm within easy reach of the region’s cultural and culinary attractions, while the sheer scale of the farm ensures privacy and a retreat-like atmosphere. For those seeking a legacy property, conservation showcase, sporting retreat, or family compound, Duvall Farm represents an unparalleled opportunity. With its rich mix of land, water, and architecture, it is a property of enduring importance — one that honors the past while offering a wide horizon for the future. Please Note, tax ID and Property Taxes are showing the information on record for the improved parcel. Please contact agent for additional parcel information.

6150 Oxford Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$6,299,000
9 Beds ⋅ 9 Baths
A Masterpiece on the Potomac The largest and most iconic sale in Prince George’s County—a breathtaking sanctuary of luxury and distinction. Nestled on 10.57 acres of pristine landscape, this palatial 16,000 plus -square-foot residence offers an unparalleled blend of grandeur and comfort, boasting 700 feet of Potomac River waterfront—the largest in the county. A gated entrance opens to a stately extended driveway, leading to a graceful roundabout and a grand, oversized entrance framed by majestic exterior steps. Inside, a two-story atrium foyer with marble floors and a sweeping double-curved staircase welcomes you to an environment of timeless elegance. The main level is designed for both lavish entertaining and relaxed living, featuring two formal dining rooms, a spacious living room, a game room, and a large open kitchen with an extended island eat-in area adjacent to the family room. Direct access to the rear balcony offers seamless indoor-outdoor flow and panoramic views. The indoor pool, visible from the main level, invites serenity, complemented by a pool deck with steps to the lower pool area. The estate’s expansive layout includes 9 total bedrooms, a bonus room, 7 total full bathrooms, and 1 half bathroom. The upper level showcases five bedrooms, a bonus/sitting room, and an opulent primary suite with a private terrace capturing sweeping views of the Potomac River, the Woodrow Wilson Bridge, and neighboring Alexandria, VA. A fully functional attic space provides versatility with a spacious bedroom, a multi-use flex room, and an upper loft. The meticulously designed basement offers a 2-bedroom apartment with a full bathroom and a large eat-in kitchen, a theater room, a lounge area, and direct access to the in-ground pool area and a side 5-car garage. Embrace the ultimate in luxury living where architectural beauty, sophisticated interiors, and unrivaled waterfront vistas create an extraordinary residence without peer.

11501 Riverview Rd, Fort Washington

Listing courtesy of TTR Sotheby's International Realty. Contact: 3015161212
$5,999,999
5 Beds ⋅ 5 Baths
Welcome to “The Nautilus” – one of the most breathtaking waterfront properties in all of Maryland. This stunning 4-story home is located in the quiet harbor area of West Ocean City and offers unmatched views in every direction. Look out over the Ocean City Inlet, downtown skyline, Assateague Island, and the Atlantic Ocean—all from your own home. It truly feels like you’re living on a luxury cruise ship, surrounded by water and endless horizons, while enjoying the calm and privacy of the bay. Enjoy 5 bedrooms, 3 full and 2 half bathrooms, 2 full kitchens, a private elevator, and an incredible rooftop deck with sunrise and sunset views. Step out your back door to your private dock with a boat slip and lift, giving you direct access to the water. This location offers both peace and convenience—tucked away in a quiet neighborhood but just minutes from Ocean City’s beaches, restaurants, and marinas. The Nautilus is more than a home—it’s a once-in-a-lifetime property with views you won’t find anywhere else.

12957 Harbor Rd, Ocean City

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382
$5,995,000
8 Beds ⋅ 6 Baths
See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$5,995,000
6 Beds ⋅ 6 Baths
Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47± acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that was at one time, the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite.

27293 Southside Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$5,950,000
8 Beds ⋅ 10 Baths
Permit ready, New Construction Opportunity: Nestled on a premier, level 0.57-acre lot in the prestigious Arrowood subdivision, this exquisite new construction estate designed by renowned GTM Architects (completion 2027) embodies the pinnacle of luxury living and offers approximately 9,800sf of conditioned space. A harmonious blend of traditional and transitional design, the residence boasts an all-brick or stucco exterior, elegant cast stone entry porch, and meticulously curated finishes across four spectacular levels. <br> <br> Inside, a grand center-hall foyer is flanked by formal living and dining rooms, flowing seamlessly into an expansive family room and a chef’s gourmet kitchen outfitted with a butler’s pantry and custom built-ins. Designed for effortless multigenerational living and unmatched privacy, the estate features 8 spacious bedrooms—each with an ensuite bath and large closet—plus two elegant powder rooms. <br> <br> The Ultimate Entertainment Oasis - The fully finished, daylight lower level with five large south facing windows features soaring almost ten-foot ceilings and is primed for world-class leisure: a state-of-the-art integrated surround sound system in the recreation room, a sophisticated 19th hole bar overlooking the dedicated golf simulator room with almost eleven-foot ceiling, and large exercise room with glass door. <br> <br> Attic-Level Wellness Retreat - Escape to the top floor, a thoughtfully designed wellness space illuminated by three large skylights featuring a private sauna, beverage bar, 6th bedroom up, and full bathroom complete with oversized tub shower. <br> <br> Resort-Style Outdoor Living - Transition outdoors to your private paradise, featuring heated saltwater pool, beautifully landscaped grounds, and pool bar with full bathroom and laundry. Enjoy twilight entertaining on the screened porch with grilling area, or central covered porch with skylights, fully illuminated by custom exterior lighting. <br> <br> Luxury & Convenience - Elevator serving multiple levels for long-term accessibility. Main level bedroom or office with connected full bathroom. <br> <br> • 4-Car Garage Capacity: Oversized attached garage with 12-foot ceilings, perfectly outfitted for stacking lifts, plus side bay and abundant overhead storage. <br> <br> • Smart & Secure: Advanced security measures, central vacuum system, two laundry rooms, and three cozy gas fireplaces. <br> <br> Experience the epitome of modern sophistication, where every detail can be tailored for the discerning homeowner. Note: Final pricing depends on selected options and lot settlement timing. See approved floor-plans in photo stream.

9113 Redwood Ave, Bethesda

Listing courtesy of Premier Properties, LLC. Contact: (301) 873-3221
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