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1455 Cayots Corner Rd, Chesapeake City
$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:

3366 Belmont Ave, Glyndon
$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:

19700 Mulberry Fields Rd, Leonardtown
$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:

938 Old County Rd, Severna Park
$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:

5124 Wissioming Rd, Bethesda
$12,500,000
5 Beds ⋅ 8 Baths
Overlooking the Potomac River in scenic Glen Echo, Wissioming Road is a modernist masterpiece designed by the critically acclaimed Robert M. Gurney, FAIA. In the architect’s signature style, interconnected structures harmonize with the site’s natural topography to create a striking visual cohesion and uninterrupted views of the roaring river beyond. A spectacular addition by Christopher Tucker, constructed by Steve Howard of Square One Development, enhances Gurney’s original vision of Corten steel, rich wood, and expansive glass. The approach is both bold and intentional—anchored by a generous covered carport and an attached, heated four-car garage, offering exceptional space for the automobile enthusiast. A bridge crosses whimsical, High Line–inspired landscaping in the central courtyard, leading to the home’s dramatic main entrance. Inside, the main living area is a masterclass in luxurious minimalism. Slender steel window frames—laid out in a Mondrian-inspired pattern—frame sweeping views of the Potomac, while large, unbroken slabs of white terrazzo flooring reflect natural light to heighten the sense of space. Rich mahogany paneling conceals the television, and a floating bamboo vanity distinguishes the formal powder room. An adjacent screened-in porch with its own fireplace and television allows for four-season enjoyment. The chef’s kitchen is nestled beneath an upper-level mezzanine, illuminated by double-height, floor-to-ceiling windows with motorized shades. Sleek European Varenna by Poliform cabinetry conceals a suite of professional-grade Miele appliances, subtly accentuated by architectural Delta lighting. The space opens into a generous dining area, perfectly positioned to overlook the central courtyard and create a seamless indoor-outdoor experience. A full butler’s pantry with redundant appliances and access to the three-level elevator complete the main level. A floating steel staircase leads to the upper level, introduced by a frosted Shoji-paneled wall. Three secondary bedrooms—each with an ensuite bath and walk-in closet—are connected by a shared sitting room. The primary suite commands its own private wing, accessed via a floating glass bridge. Stained ebony floors and two private offices set the tone for the refined sanctuary that follows. Sweeping river views pour into the main sleeping area through floor-to-ceiling windows and continue onto the full-length private balcony, while custom blackout curtains allow for serene retreat. The limestone-clad bath is a study in indulgence, featuring a freestanding tub set against glass, a walk-in shower, sauna, and a separate dressing room. On the lower level, the main recreation area spans more than 52 feet. Polished concrete floors, a wet bar, and a temperature-controlled, illuminated 1,000-bottle wine cellar create an effortless environment for entertaining. In the opposite wing, a professional fitness center with padded flooring, its own HVAC system, and a Helo sauna connects to a fully self-sufficient guest suite complete with private bath, patio, and kitchenette. The lower level’s architectural pièce de résistance is a split-level library. A cozy upper-tier reading nook accesses a cantilevered glass bridge that overlooks the dramatic den below. An unbroken wall of built-ins spans both levels, anchored by a linear gas fireplace and double-height window wall with direct access to the lower patio. Out back, a magnificent 66-foot lap pool serves as the property’s showstopping centerpiece. A built-in grill and fireplace on the rear terrace facilitate al fresco entertaining, framed by dramatic views of the Potomac. An interconnected fortress of luxury, the residence features computer-controlled Lutron lighting, Sonos surround sound, Honeywell security, and video surveillance.

5124 Wissioming Rd, Bethesda

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

5 Franklin St, Annapolis
$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:

1546 Teal Dr, Ocean City
$11,995,000
4 Beds ⋅ 5 Baths
1546 Teal Drive, Ocean City, Maryland presents a singular opportunity: the bay’s only private island estate, offering more than three acres of privacy in the heart of Ocean City. Hidden from view behind a gated entrance, the arrival unfolds across a private 120-foot vehicular bridge to an extraordinary world of its own—native marshland, coastal landscape, abundant birdlife and panoramic open-water views, with both sunrise and sunset reflected across the bay. Just three blocks from the beach and iconic Ocean City Boardwalk, this remarkable setting offers the rare combination of seclusion and accessibility. By water, the Ocean City Inlet and Assateague Island are only minutes away, with Harbour Island—home of the internationally renowned White Marlin Open, the world’s largest billfish tournament—nearby. Included with the estate is an adjacent, buildable .29-acre waterfront parcel with approximately 95 feet of bulkheaded shoreline, boardwalk, paved driveway, irrigation and landscaping, creating possibilities for a future guest house or single-family residence, additional parking or expanded waterfront enjoyment. At the center of the island is an approximately 5,000-square-foot shingle-style residence inspired by the enduring coastal architecture of Nantucket and enhanced by renowned Lyman Perry Architects Ltd. of Nantucket, Massachusetts. Inside, craftsmanship and character reveal themselves through custom millwork, Carlisle wide-plank hand-finished pine floors and expansive Andersen doors framing the water beyond. A dramatic 24-foot atrium beneath an oversized skylight is anchored by a soaring Coral Rock wall with an integrated fireplace, creating a striking architectural focal point visible from both levels and connecting the surrounding living spaces. The kitchen and family room were designed for gathering, with custom solid-birch cabinetry by Premier Cabinetry of New Holland, Pennsylvania, and a custom 5-foot by 10-foot teak island. A private office with custom built-ins, guest suite and full bath complete this level. Upstairs, an open bridge overlooks the atrium and leads to the expansive four-room primary suite with bayfront deck, vaulted ceilings, custom cherry built-ins, generous dressing rooms and en-suite bath. Two additional bedrooms offer en-suite baths and private decks. Outdoors, the island becomes its own waterfront resort, with approximately 3,250 square feet of wraparound decking leading to a pool and spa, gazebo bar, full bath, private docking, 10,000-pound boat lift and fish-cleaning station—all surrounded by open water and coastal sky. Significant recent investment includes bulkhead improvements, reinforced helical pilings, bridge renovations, active security and surveillance systems, and maintained structural and mechanical systems. More than a waterfront residence, 1546 Teal Drive is a private island estate of extraordinary rarity—an irreplaceable setting where architecture, land, water and privacy converge in the heart of Ocean City.

1546 Teal Dr, Ocean City

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

933 Hillside, Lutherville Timonium
$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, Lutherville Timonium

Listing courtesy of Krauss Real Property Brokerage. Contact:

3344 Harness Creek Rd, Annapolis
$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:

1089 Nesbitt Rd, Colora
$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). Photos #6, #9, #13, #18, #28, #33, #39, #51, #58, and #61 are AI-generated conceptual images depicting potential improvements and/or uses for the Conference Center, Tenant House, and Lodge. These images are for illustrative purposes only and do not represent existing conditions.

1089 Nesbitt Rd, Colora

Listing courtesy of Engel & Volkers Annapolis. Contact:

8 Spa View Cir, Annapolis
$9,998,000
5 Beds ⋅ 6 Baths
NEW PRICE — $9,998,000. A rare opportunity to acquire an extraordinary Annapolis waterfront estate, now thoughtfully repositioned for today’s discerning buyer. Set along 168' of Spa Creek waterfront, this approximately 6,000 SF residence is privately positioned within an exclusive enclave of just three homes. The private deep-water dock offers approximately 8' MLW and accommodates a 60–70' sailboat or yacht with wide beam. Cruise to City Dock and downtown restaurants in minutes, or enjoy panoramic water and unobstructed Annapolis skyline views from home, including front-row views of the Blue Angels, fireworks and annual boat parade. The heated saltwater pool, expansive Ipe deck and beautifully landscaped grounds create exceptional waterfront entertaining. Meticulously maintained and extensively renovated by Pyramid Builders, the architecturally distinctive residence features a dramatic marble foyer, floor-to-ceiling windows, solid wood doors, rich stained black oak flooring and two striking gas fireplaces. The sophisticated white kitchen features Sub-Zero refrigeration, a eight-burner Viking cooktop, high-gloss Premier cabinetry and Neolith porcelain countertops, complemented by designer lighting and a striking floating staircase. A private speakeasy with a custom marble-topped bar creates an intimate setting for cocktails and entertaining. The residence offers 4–5 bedrooms and 5 full and 1 half baths, including a first-floor bedroom suite. A two-car garage, generous parking and private pier complete this exceptional Murray Hill waterfront offering. Enjoy deep-water boating, resort-style outdoor living, sophisticated entertaining and downtown Annapolis—all from one extraordinary private setting.

8 Spa View Cir, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

6920 Travelers Rest Cir, Easton
$9,950,000
4 Beds ⋅ 6 Baths
Set on the coveted shores of the Tred Avon River, this extraordinary waterfront estate is a rare offering, combining deep-water boating, a private sandy beach, a substantial main residence, separate guest accommodations, and an exceptional collection of lifestyle amenities. From the first approach, the property unfolds as a private Eastern Shore compound, where elegant architecture, sweeping river views, and resort-caliber amenities are seamlessly integrated into a singular waterfront setting. The four-bedroom, five-and-a-half-bath main residence is both impressive and inviting. A dramatic two-story living room features hardwood floors, a fireplace, custom millwork, and abundant natural light, while the waterside den offers a more intimate retreat with a gas fireplace, custom bookshelves, and a wall of glass framing views across the Tred Avon. A spacious screened porch and expansive Ipe decking extend the living spaces outdoors and provide direct access to the waterfront. At the heart of the home, the kitchen is equipped with a Sub-Zero refrigerator, gas cooktop, double ovens, stainless steel dishwasher, granite countertops, and white cabinetry, along with generous space for casual dining. A first-floor office and laundry room add everyday convenience, while dual staircases provide easy access throughout the home. The first-floor waterfront primary suite is a private sanctuary with its own fireplace, sitting room with custom bookshelves, two walk-in closets with custom shelving, and a beautifully appointed bath featuring a waterside soaking tub, dual vanity, and walk-in steam shower. Each additional bedroom is en suite, creating comfortable and private accommodations for family and guests. Outside, the property transforms into a private waterfront retreat. A heated lap pool, hot tub, and sandy beach create distinct places to relax along the river, while a scenic walking path winds through wildflower gardens and open space, reinforcing the estate’s remarkable sense of privacy and scale. The pool house makes outdoor entertaining effortless, with a full kitchen, stainless steel appliances, gas range, laundry facilities, and an outdoor shower. A separate three-bedroom, two-bath guest residence provides exceptional additional accommodations with hardwood floors, a full kitchen, laundry, garage, and a large deck overlooking the Tred Avon—ideal for extended family, guests, or multi-generational living while preserving the privacy of the main residence. For those drawn to the water, the property delivers. A private pier offers 6+ feet of water at mean low water, three slips, two boat lifts, water and electric—providing exceptional deep-water access for a wide range of vessels. From here, spend the day cruising the Tred Avon and exploring the waterways of the Chesapeake Bay. A rip-rapped shoreline provides protection while preserving the property’s connection to the river. With a three-car garage, irrigation system, extensive custom millwork, guest and pool houses, heated pool, sandy beach, and substantial boating infrastructure, this is far more than a waterfront home. It is a complete Eastern Shore estate—a private compound where the residences, grounds, and waterfront amenities come together to create an exceptional lifestyle on the Tred Avon.

6920 Travelers Rest Cir, Easton

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

3285 Harness Creek Rd, Annapolis
$9,500,000
6 Beds ⋅ 10 Baths
Located on a private 2.5-acre lot in Wimbledon Farms, this waterfront estate home, designed by Cathy Purple Cherry and constructed by West River Builders, is truly a masterpiece in design and quality. The 3-level home – complete with elevator -- takes full advantage of its waterfront setting that includes 400 ft of shoreline. Facing Quiet Waters Park, the ever-changing view includes brilliant fall foliage, deer by the water’s edge, and osprey circling overhead. Stroll down to the 100 ft private pier with deep-water slips. There’s 7 ft water depth at the dock; Harness Creek is a recognized hurricane hole so this is the perfect spot for boats to ride out a storm. The 20 ft x 40 ft saltwater pool has a spacious ipe deck and two Hanso pergolas provide shade with wonderful water views. Six bedrooms, each with a private ensuite bath, a gourmet kitchen, and wrap-around screen porches and decks provide space for both casual living and grand entertaining. Upon entering, there is a gracious paneled foyer that opens to the living room. With Brazilian cherry floors, a gas fireplace with marble surround, and built-in bookcases, this room has fabulous water views and opens to one of the screened porches on this level that invite outdoor living. To the right is the heart of the home – the great room. It includes a just remodeled chef’s kitchen with multiple work areas, a family room, and the dining area. The kitchen includes Taj Mahal leathered countertops, two wall ovens, two Bosch dishwashers, a warming drawer, instant hot dispenser, Wolf 5-burner gas cooktop, and KitchenAid side-by-side refrigerator. There’s also a wet bar with beverage cooler. The family room has a wood-burning fireplace with raised hearth and stone surround; there’s also a spacious workspace with built-in bookshelves. The dining area overlooks the water, and there’s access to both screened porches. The main level also features a fabulous guest suite: there is a large bedroom with water views, walk-in closet, and a private bath with radiant heated floor. In addition, there are two powder rooms and a mudroom with three closets and an abundance of storage space. The main level has 10 ft ceilings and 8 ft interior doors. Upstairs, the primary suite is an owner’s dream escape. There’s a spacious bedroom with water views, dark cherry floors and a gas fireplace. The study, with wet bar, built-in shelves and file drawers, leads to a small reading room – with water views. The spa-like bathroom, with radiant heated floor, includes a separate water closet room, jetted tub with marble surround, oversized steam shower, and separate vanities. Step onto the private screened porch to enjoy a cup of coffee in the morning. The primary suite also includes two large walk-in closets and a laundry room. There are three additional water view bedrooms on the second floor, each with private bathroom and walk-in closet. The main laundry is in a dedicated room with ample storage. There’s also a walk-in cedar closet. All of the bedrooms and closets that have carpeting were re-carpeted in 2026. The walk-out lower level has a huge game room that includes a big screen TV, wet bar, and full bathroom. From here, you can step out to the bluestone patio that leads up to the pool. There is a half-bath off the patio, accessible for pool visitors. The 6th bedroom with ensuite bathroom also has peaceful views, and multiple closets. The main utility room houses the commercial grade water treatment system. It has a garage door for easy access to boat supplies and equipment servicing. A secondary utility room houses the elevator mechanism and reverse osmosis treatment system. A third unfinished area has the camera and internet systems. This exceptional home offers sophisticated waterfront living just minutes from the heart of Annapolis and the Chesapeake Bay. The year-round beauty of this scenic setting and unrivaled design is truly unsurpassed!

3285 Harness Creek Rd, Annapolis

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

12903 Windy Dr, Ocean City
$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:

7112 Natelli Woods Ln, Bethesda
$8,995,000
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:

750 Cassidy Wharf Rd, Earleville
$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:

964 Taylors Island Rd, Madison
$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:

2035 Maidstone Farm Rd, Annapolis
$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:

13320 Signal Tree, Potomac
$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:

27295 Southside Island Creek Rd, Trappe
$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:

8620 Bozman Neavitt, Saint Michaels
$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:

8880 Bradley Blvd, Bethesda
$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 Sotheby's International Realty. Contact:

3600 Butler Rd, Glyndon
$8,200,000
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:

7600 Exeter Rd, Bethesda
$7,995,000
8 Beds ⋅ 8 Baths
Originally built in 1918 by renowned Washington architect Robert F. Beresford, this extraordinary Tudor Revival estate stands as one of Edgemoor's most significant grande dames. More than a century later, the home continues to embody the timeless elegance and architectural integrity that first distinguished it. From 2016 to 2018, the residence underwent a comprehensive restoration and renovation led by Hutchinson & Associates LLC in conjunction with John L. duFief, Inc., with interiors curated by Maureen A. Daly & Associates. Set on a remarkably serene and impeccably landscaped one-acre lot, this exceptional property combines historic significance, meticulous craftsmanship, and thoughtful architectural design rarely found today. Spanning more than 7,500 square feet of finished interior space, 7600 Exeter Road offers eight bedrooms and seven-and-a-half bathrooms. Ideal for Washington’s most discreet homeowner, the welcoming horseshoe driveway provides an elegant entrance for entertaining, while everyday access flows from a side entrance through a separate driveway and expansive motor court with parking for six vehicles, complemented by an oversized two-car detached garage. The grand entrance foyer introduces exquisitely restored interiors, with direct views of the estate's majestic rear grounds designed by Fritz & Gignoux Landscape Architects. Beautifully proportioned entertaining spaces include a formal living room with custom built-ins and fireplace, a spacious family room or formal dining room with window seat and fireplace, and a handsome library with custom built-ins and fireplace. A spectacular conservatory-style eat-in kitchen addition by Tanglewood Conservatories serves as the heart of the home, featuring custom sapele mahogany millwork, radiant-heated bluestone flooring, top-of-the-line appliances, a large stainless-steel island, butler’s pantry, and abundant natural light. The northern wing includes a sitting room with private garden access, kitchenette, laundry area, guest bedroom suite with sitting area and ensuite bath, additional full bath, and oversized laundry room. A secluded powder room, multiple coat closets, and back staircase complete the main level. The sun-drenched front staircase leads to a luxurious primary suite with fireplace, private sleeping porch, multiple walk-in closets, dedicated dressing room, and dual primary bathrooms. Three additional bedrooms—two with fireplaces and ensuite baths—plus a full hallway bath and laundry/linen closet complete the second level. The third floor offers three additional bedrooms, a full hallway bath, laundry room, and large conditioned attic storage. The lower level provides finished space ideal for recreation or future customization, along with a large utility room with exterior access. The estate's rear grounds are among its most coveted features. Mature trees and established landscape screening create a rare level of seclusion, while award-winning landscape designers reimagined the property with extensive plantings, a fruit orchard, multi-zone irrigation, landscape lighting, enclosed fencing, elegant Serra Stone masonry, an enchanting water feature, and an oversized pergola draped with cascading vines. Ample space for recreation and gatherings is complemented by a secluded spa surrounded by lush greenery. Despite its exceptional privacy, 7600 Exeter Road is within easy walking distance of downtown Bethesda's boutique shopping, acclaimed dining, parks, trails, entertainment, and public transportation. The historic Edgemoor Club, with swimming and tennis facilities, is just down the block. Conveniently positioned in the Capital Region, the property also offers easy access to multiple airports and rail services. An exceptional one-of-a-kind offering, this English-style estate presents a rare opportunity to own a piece of history in one of the region's most prestigious neighborhoods.

7600 Exeter Rd, Bethesda

Listing courtesy of Washington Fine Properties, LLC. Contact:

8901 Durham Dr, Potomac
$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:

423 Benfield Rd, Severna Park
$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:

8612 Tilghman Island Rd, Wittman
$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:

Glyndon
$7,900,000
7 Beds ⋅ 7 Baths
Live authentically. Magnificent stone estate tucked away overlooking Worthington Valley and beyond. Upper Melinda awaits perched on 249.94 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. Property is subject to conservation easement. ••Do not drive to property without an appointment.

Glyndon

Listing courtesy of Krauss Real Property Brokerage. Contact: