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$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

$5,895,000
5 Beds 6 Baths
Set on 31 private acres along the peaceful waters of Hunting Creek, this exceptional Eastern Shore estate combines timeless architecture with modern sophistication. With over 1,000 feet of waterfront and approximately 6 feet of mean low water, the property offers deep-water access, stunning views, and an unmatched sense of privacy. The five-bedroom, five-and-a-half-bath residence has been completely renovated from top to bottom, showcasing impeccable finishes, custom millwork, and thoughtfully designed spaces throughout. Sunlight pours through large windows that frame panoramic views of the creek and surrounding landscape. The home features two luxurious primary suites, each offering a private retreat with refined finishes, spa-inspired baths, and generous closets. Two additional bedrooms share a beautifully designed ensuite bathroom, while a first-floor bunk room with its own bath provides the perfect space for guests. Outside, the saltwater pool overlooks the water, surrounded by manicured lawns and mature trees that extend to the shoreline. A long, tree-lined driveway creates an impressive approach to the home, setting the tone for the peaceful retreat that awaits. Located just minutes by car to Easton and St. Michaels—and even closer by boat—this Hunting Creek estate captures the very best of the Chesapeake Bay lifestyle: elegance, tranquility, and effortless connection to the water.

9170 Hunting Creek Ln, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$5,850,000
7 Beds 6 Baths
Introducing White Swan Point, an exceptional Chesapeake waterfront estate offering one of the Eastern Shore's most commanding settings. Positioned at the confluence of Broad Creek and the Choptank River, the property enjoys nearly 5,000 feet of shoreline with sweeping western and southwestern vistas that capture spectacular sunsets, cooling summer breezes, and an ever-changing panorama of sailboats, yachts, and waterfowl. With close proximity to major metropolitan areas, this private waterfront retreat offers a rare combination of architectural quality, recreational opportunity, and lasting investment. Whether envisioned as a family compound, executive retreat, or waterfront residence for entertaining on a grand scale, the setting delivers an experience that is increasingly difficult to replicate along the Chesapeake Bay. Constructed in 2006 by its builder as their personal residence, the approximately 8,500 square foot home reflects enduring craftsmanship and design throughout. Seven ensuite bedrooms provide generous accommodations for family and guests, while soaring ceilings, three fireplaces, richly appointed living spaces, and a sunlit morning room create an atmosphere that is both elegant and welcoming. A distinctive turret crowns the residence, providing a remarkable vantage point from which to enjoy the sunset as it settles across Broad Creek. Outdoor living is at the heart of the estate. Expansive terraces, waterside porches, and beautifully landscaped gathering spaces transition naturally toward the shoreline, where the pool, pool house, outdoor kitchen, and riverfront fire pit become the backdrop for unforgettable evenings overlooking the water. Nearly every outdoor amenity has been carefully positioned to take advantage of the property's extraordinary western exposure and uninterrupted water views. For the boating enthusiast, the estate offers exceptional privacy and water access along Broad Creek, providing an ideal setting for cruising to St. Michaels, Oxford, Tilghman Island, and destinations throughout the Chesapeake Bay. Approximately 1,900+/- feet of stone revetment protects the prominent shoreline, while an additional 2,500+/- feet along the quiet waters of Bridge Creek remains preserved in its natural state, creating a diverse waterfront environment rich with wildlife and native vegetation. Beyond the residence, the property continues to offer remarkable flexibility. Approximately 13 acres are under cultivation with an additional 3.5 acres in pasture, presenting opportunities for equestrian pursuits, hobby farming, or simply preserving the estate's open landscape. A substantial 40-foot by 60-foot barn includes workshop space, equipment storage, and a second-floor caretaker or guest apartment, providing exceptional utility for managing the property or accommodating extended stays. White Swan Point represents far more than an extraordinary waterfront home. It is an opportunity to own one of Maryland's signature Chesapeake estates, where privacy, recreation, architectural quality, and timeless waterfront living come together in one exceptional offering.

24390 Deep Neck Farm Ln, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$5,750,000
6 Beds 7 Baths
Set on a prominent .75-acre corner lot, 7101 Longwood Drive is a masterfully executed custom residence with design-forward panache. Built in 2018 by GBI Builders, designed in collaboration with architect Carmel Greer and interior designer Julie Geyer, this stunning home spans 9,100 square feet across four meticulously finished levels. The home unfolds with a sense of scale (note the 11’ ceilings on main level), light, and intention at every turn with high-end designer finishes including stunning custom lighting. Outdoors, the home transforms into a private resort surrounded by mature trees and landscaping for added privacy with a stunning heated in-ground pool, expansive patio, and outdoor kitchen. A grand, light-filled foyer makes an unforgettable first impression with a Murano glass chandelier and anchored by a sweeping, sculptural staircase with refined detailing that rises dramatically through the home. Wide-plank white oak hardwood floors, elegant millwork, and soaring ceilings carry throughout, setting a cohesive tone of understated luxury. Formal living and dining rooms are both gracious and inviting—ideal for entertaining—while the dining room connects seamlessly to the kitchen via a fully outfitted butler’s pantry, complete with custom cabinetry and additional prep space. The formal living room is anchored with a fireplace, white oak wood in ceiling beams, and doors leading to the covered patio with retractable screens. The kitchen is a true centerpiece: an expansive, chef-caliber space with Calacatta Vagli counters and backsplash, an oversized island, high-end appliances (including a Dacor range and fridge/freezer), custom cabinetry, Brizo fixtures, and designer lighting. A sun-drenched breakfast nook, wrapped in windows and additional built-in cabinetry. The kitchen flows effortlessly into the family room, where a statement fireplace and coffered ceilings create a warm yet elevated gathering space. Large glass doors blur the line between indoors and out. A private office with bespoke built-ins offers a quiet retreat, while a thoughtfully designed mudroom with ample storage connects directly to the three-car garage. Finishing this level are two powder bathrooms. Upstairs, the primary suite is both serene and sophisticated, featuring white oak wood in ceiling beams, custom automated window treatments, dual custom walk-in closets, and a spa-like bath clad in luxurious finishes —complete with Nero Marquina marble counter and floors, a freestanding soaking tub, oversized glass-enclosed carrara shower and walls, waterworks hardware, and dual vanities. Three additional bedrooms are beautifully appointed, accompanied by two well-designed baths and a versatile lounge space ideal for relaxing or studying. The top level provides an additional private suite. The lower level is designed for indulgent living and entertaining, featuring a sprawling recreation space, a showstopping wine cellar—with a biometric lock, standalone cooling system, extensive storage and space for a tasting table—serves as both a functional and visual focal point. This level also includes a fitness room, an additional bedroom and full bath, and storage. The professionally landscaped exterior serves as an extension of the home and is the perfect place to enjoy the upcoming summer months. A beautifully designed patio anchors the backyard, featuring a covered living area with retractable screens, heaters, a fan, and a fireplace. The outdoor kitchen is fully equipped with Granite countertops, a mini-fridge, built-in grill and gas burner, warming drawer, and ice maker for effortless entertaining, while the pool—set against lush landscaping—creates a striking and tranquil backdrop. A circular driveway enhances the home’s stately curb appeal, complemented by a secondary driveway leading to the side-entry three-car garage.

7101 Longwood Dr, Bethesda

Listing courtesy of Compass. Contact: (301) 298-1001

$5,675,000
3 Beds 4 Baths
Stately French Villa on Spa Creek in downtown Annapolis! This jewel box of a home was designed and built by a renowned local architect as the culmination of an award-winning career. Offered completely turn-key, this exceptional residence conveys fully furnished and thoughtfully appointed—including furniture, fully equipped kitchen, linens, etc —allowing you to arrive with nothing more than a suitcase and begin enjoying the Annapolis waterfront lifestyle from day one. The unrivaled architectural detail, exquisitely curated finishes, and sweeping views across Spa Creek elevate this residence into a class of its own. Privately positioned at the end of a quiet street within one of downtown’s most coveted waterfront enclaves, this 3-bedroom, 3.5-bath retreat is equally suited as an elegant weekend escape or a full-time residence. Dramatic Palladian windows bathe the interiors in natural light while perfectly framing the ever-changing harbor views. At the heart of the home, the gourmet kitchen—appointed with custom cabinetry, premium appliances, and a striking designer hood—flows seamlessly into both the formal living room and inviting family room, each enhanced by a gas fireplace and captivating water vistas. A main-level secondary primary suite offers comfort and flexibility for guests of all generations. Upstairs, the extraordinary waterside primary suite features vaulted ceilings, walls of glass, a gas fireplace, spa-inspired bath with soaking tub, and a custom dressing room with center island. A private balcony provides the ideal perch for sunrise coffee or sunset reflections overlooking Spa Creek, Annapolis Harbor, and Eastport. Designed for effortless waterfront living, two deep-water piers with approximately 9 feet of MLW accommodate substantial vessels, with immediate access to the Severn River, the Chesapeake Bay, and beyond. Walkable to the shops, restaurants, and charm of downtown, this rare offering delivers convenience, privacy, elegance, and ease in one remarkable package. Welcome Home!

1 Shipwright Harbor, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$5,500,000
6 Beds 9 Baths
Introducing an extraordinary new-construction luxury residence set for completion in 2026, located in the prestigious Avenel community of Bethesda. This architectural masterpiece is thoughtfully designed to blend modern elegance with timeless livability, offering an unparalleled lifestyle in one of the region’s most sought-after settings. Nestled on a quiet cul-de-sac and backing to a serene wooded vista, this impressive home features 6 bedrooms and 8 bathrooms, crafted with exceptional attention to detail. A three-car garage, elevator, and expansive indoor–outdoor entertaining spaces elevate convenience and sophistication. The spectacular custom pool and tiered outdoor living spaces offers year-round entertaining. At the heart of the home, a dramatic two-story great room that showcases floor-to-ceiling windows, flooding the interior with natural light and capturing sweeping views of the surrounding nature. The open-concept design flows seamlessly into a gourmet designer kitchen and an additional catering or prep kitchen, ideal for effortless entertaining. Retreat to the luxurious bedroom suites, each offering refined finishes, generous proportions, and spa-inspired bathrooms. The primary suite includes a fireplace and a private walk-out balcony overlooking the peaceful rear grounds—an intimate sanctuary for morning coffee or evening relaxation. On the lower level, the home continues to impress with direct access to the poolside patio and outdoor entertainment spaces. This level includes a full bedroom suite, and a state-of-the-art Zen spa facility designed for relaxation and rejuvenation. A stylish wet bar anchors the recreation space. A striking glass-front wine storage and display area adds a sophisticated focal point, perfect for showcasing a curated collection. An additional dedicated room provides the ideal setting for a golf simulator or private theatre. The exterior is equally impressive, highlighted by a spectacular custom pool, tiered outdoor living spaces, and room for year-round entertaining. Located within the coveted Avenel community—featuring a clubhouse, pool, tennis, and optional golf membership—this exceptional residence presents a rare opportunity to own a newly built estate in an elite Bethesda neighborhood.

7009 Natelli Woods Ln, Bethesda

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: yanira@lnf.com

$5,495,000
7 Beds 6 Baths
Nestled on a sprawling, level half-acre lot, along a verdant stretch in the heart of sought-after Chevy Chase Village Section Three, 3626 Raymond Street is the classic craftsman charmer. From the curbside, the home’s vibrant yellow shingle and green trimmed exterior radiates character amongst today’s cookie cutter residences. A low stacked-stone wall is bifurcated by a central flagstone walkway offering an elegant approach across the manicured front lawn, stepping up into the charming covered porch. Adjacent is a paver motor court offering ample surface parking in addition to a neatly integrated carport. The Hollywood film-worthy interiors continue the old-world ethos, with stunning, rich, intricate millwork throughout, showcasing a level of craftsmanship from a far bygone era. Meticulous curation has infused the century-old space with fully modern amenities to suit present-day lifestyle demands. The central foyer’s showpiece is the grand staircase, bent around an integrated bench and whose intricacy is peerless. Embassy-sized formal living and dining rooms flank the entryway in a traditional center hall configuration, setting the tone for deceptively grand spaces. The former features a roaring fireplace and two full exposures to natural light. The latter has a buffet cabinet built into the bay window sill, coffered ceiling, pinhole lighting to establish a sophisticated ambiance, and flows into a recessed library nook surrounded by built-ins. The main informal living area is the spacious family room, also featuring a wall of built-ins opposite a set of sliding doors opening onto the covered rear porch, an ideal setting for al fresco dining or entertaining. The family room is connected to the kitchen area by a spectacular transverse gallery, its floor-to-ceiling picture windows blurring the lines between indoor and outdoor living. A decidedly more modern space, the kitchen connects to the rest of the main level via a custom, fully wooden island with integrated seating, but introduces a commercial-grade Wolf range and state-of-the-art, full size refrigeration for the culinary enthusiast. An adjacent, ethereal breakfast nook and mudroom area complete the main level. A private study introduces the upper level primary suite, occupying a substantial portion of the home’s footprint. The bedroom is privately tucked away and enjoys lush views from a wall of glass, while the dressing area comprises three walk-in closet areas on dual levels. In stark contrast, the primary bath is lavishly clad in Calacatta marble and generously equipped with dual inset vanities, a separate full powder room, freestanding clawfoot tub, walk-in shower enclosure, and Waterworks fixtures. Completing the upper level are a bedroom suite, two additional bedrooms sharing a hall bath, and a convenient laundry room. Two additional bedrooms, easily repurposed as bonus spaces, a full bath, and a communal sitting area are found on the top level. The self-sufficient lower level intertwines leisure and function with a recreation room, kitchenette, bedroom, full bath, and second laundry room, while a private office wing opposite spans the entire depth of the home. Another highlight of the home is the outdoor space, also deceptively large. The expansive paver patio, stepped down from the covered porch, is dominated by a sprawling 60-foot heated pool with automatic cover.

3626 Raymond St, Chevy Chase

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

$5,495,000
6 Beds 6 Baths
Luxury lakeview living at its finest. Perfectly positioned in one of Deep Creek Lake’s most desirable communities, this custom-built mountain retreat offers sweeping lake views, exceptional craftsmanship, and thoughtfully designed living spaces throughout. Built with quality and longevity in mind, the home showcases superior construction, soaring vaulted ceilings, exposed wood beams, expansive windows, and a stunning floor-to-ceiling stone fireplace that anchors the heart of the home. Designed for entertaining, the gourmet kitchen flows seamlessly into spacious dining and gathering areas, while multiple covered and uncovered outdoor living spaces invite you to enjoy the lake and mountain scenery year-round. The lower level is built for hosting with an impressive custom bar, recreation space, and additional room for guests. Rich wood finishes, upscale details, and a warm modern mountain aesthetic carry throughout the home. Outside, a spectacular fire pit gathering area creates the perfect setting for evenings under the stars overlooking the beauty of Deep Creek Lake. Located in one of Deep Creek Lake's premier residential communities, this exceptional property offers the perfect balance of luxury, privacy, quality craftsmanship, and lake lifestyle.s, and a warm modern mountain aesthetic carry throughout the home. Striking exterior architecture with stone accents, beautifully landscaped grounds, and an ideal location near Deep Creek Lake amenities complete this exceptional offering. Whether serving as a full-time residence or private vacation retreat, this home delivers luxury mountain living in a truly special setting. NOTE: Private residence. Showings are strictly by appointment only. Please do not access the property or grounds without a confirmed appointment and licensed agent present.

218 Smith Pointe Rd, Swanton

Listing courtesy of Railey Realty, Inc.. Contact:

$5,495,000
7 Beds 8 Baths
Early opportunity to customize a bespoke residence in coveted Bannockburn Estates with the celebrated team at Francis Development. This home is sited on a pristine flat half-acre lot on a quiet side street backing to 25 acres of protected wooded parkland. Home is framed, offering a rare chance to personalize finishes and features ahead of completion. Experience nearly 9000 square feet of interior living space over 3 levels and across an 85 foot front facade with a four-car garage and an elegant all-brick exterior, plus opportunities to add a golf simulator, pool, sauna, wine cellar, custom gym, and other tailored amenities. You'll find 10 foot ceilings on the main level and lower level. Highlights of this south facing residence include a wall of large windows off the rear family room and kitchen area taking advantage of the expansive private views and flooding the home with natural light. This residence features 7 bedrooms, 7 full baths, including 1 half bath, an elevator, a first floor suite as well as both an expansive deck and patio with decadent views. Expected delivery Fall 2026 delivery.

6908 Carmichael Ave, Bethesda

Listing courtesy of Compass. Contact: (301) 298-1001

$5,450,000
7 Beds 10 Baths
Designed as the builder's personal residence, this extraordinary Bethesda estate presents a rare opportunity to own a private resort-like retreat on approximately 2.5 secluded acres. Offering approximately 15,000 square feet of finished living space across four levels, the residence combines exceptional scale, timeless craftsmanship, and unparalleled recreational amenities rarely found in the Washington metropolitan area. A long private driveway leads to two expansive motor courts, a four-car side-entry garage, and a setting that feels worlds away while remaining moments from downtown Bethesda, Potomac, and Washington, D.C. Convenient access through Avenel provides the benefits of the location without Avenel HOA fees. A dramatic two-story foyer introduces interiors designed for both grand entertaining and comfortable everyday living. Formal living and dining rooms, each anchored by a fireplace and framed by oversized picture windows, create elegant gathering spaces filled with natural light. At the heart of the home, the gourmet kitchen features professional-grade appointments, a breakfast room, butler's pantry, and walk-in pantry, all opening seamlessly to the spectacular two-story family room. Soaring ceilings, walls of windows, a floor-to-ceiling stone fireplace, and a wet bar create an impressive centerpiece for entertaining. The family room extends effortlessly to a covered indoor-outdoor terrace overlooking the estate's resort-caliber amenities, including a swimming pool, spa, fire pit terrace, and expansive private grounds. One of the home's most remarkable features is the luxurious main-level primary suite. Designed as a private sanctuary, it offers cathedral ceilings, a fireside sitting room, dual oversized walk-in closets, a private fitness room, and a beautifully renovated spa-inspired bath. A handsome study, sunroom, and two powder rooms complete the main level. The upper level offers four exceptional bedroom suites, including two secondary primary-style suites with spacious sitting areas and luxurious baths. Each bedroom enjoys a private en-suite bath and generous walk-in closet, providing comfort and privacy for family and guests alike. Designed for recreation, wellness, and multi-generational living, the walkout lower level delivers an extraordinary collection of amenities. Highlights include a spacious recreation lounge, full secondary kitchen, wet bar, media room, fitness area, guest suite, extensive storage, and a spa bath with steam shower. Glass doors open directly to the home's showstopping indoor-outdoor pool and spa, featuring a retractable roof that allows for year-round enjoyment regardless of season. Adding to the estate's exceptional lifestyle offerings is a full-size indoor basketball court; a truly rare luxury amenity that transforms the property into a private athletic retreat. Outdoors, a lighted tennis court, multiple terraces and patios, and beautifully landscaped grounds create endless opportunities for recreation, entertaining, and relaxation. Perfectly suited for multi-generational living, extended guests, or live-in staff, this remarkable estate delivers a level of privacy, scale, and resort-style living seldom available in Bethesda. Ideally located near premier dining, shopping, golf courses, and country clubs, and zoned for Carderock Springs Elementary School, Thomas W. Pyle Middle School, and Walt Whitman High School, this is a one-of-a-kind offering for the most discerning buyer.

7003 Fawn Trail Ct, Bethesda

Listing courtesy of TTR Sotheby's International Realty. Contact: 3015161212

$5,400,000
7 Beds 9 Baths
Designed to rival a private resort, this waterfront estate was built for celebrating with family and friends. Sweeping Chesapeake views set the stage for every gathering. The waterfront pool features a cascading rock waterfall, a tucked in bench, and a generous sun shelf, all overlooked by a pool house with a covered summer kitchen, bar, seating area, and full bath with AC. A curated firepit lounge, expansive patios and balconies, and a screened waterside porch bring indoor and outdoor living together for every occasion. At the shoreline, life on the Bay begins, with an expansive private beach perfect for wading, sandcastles, and quiet evenings by the water. The newly expanded L shaped pier stretches 260 feet and is engineered for serious boating, with dockage for a large yacht, 24,000 lb. and 10,000 lb. lifts, electric, R/O water, dual pedestals, and decorative lighting. Protected waters offer calm conditions for docking, fishing, crabbing, and watersports, with direct Bay access and easy cruising to Annapolis, St. Michaels, and beyond. A circular driveway centered by a gorgeous fountain leads to the entry, where a stunning two story foyer and grand staircase greet you, framed by spectacular water views. The great room features a soaring wall of glass and a fireplace, opening to a chef's kitchen appointed with Wolf and Sub Zero appliances, custom cabinetry, a conversation bar, pantry, and breakfast nook. The dining room seats twelve or more, ready for every holiday feast. The primary suite is a private waterfront retreat, with a sitting area beneath a domed ceiling, a fireplace, custom built ins, and a spa bath with heated floors, a jetted soaking tub, and a multi head shower. The waterfront game room offers a fireplace, wet bar, and large TV, while the private theater seats eight in front of a 100 inch screen, making this home the destination for family and friends year round. Upstairs, five architecturally unique bedrooms, three ensuite, include private waterfront balconies and a large activity room opening to a deck overlooking the pool, dock, creek, and bay. A fully equipped in law suite offers its own kitchen, living area, bedroom, fireplace, and attached two car garage, while a separate heated and cooled four car garage with porcelain tile and custom cabinetry serves as studio, workshop, or gym. Six fireplaces, Anderson and Palladian windows, tankless water heaters, a whole house water softener and reverse osmosis system, a 60KW whole house generator, and fiberoptic 2.5GB internet with seventeen access points bring comfort and connectivity throughout. Fully app based control manages lighting, HVAC, security, pool, spa, generator, music, locks, and network, inside and out. Tucked along a quiet private road with easy access to the Bay Bridge, Annapolis, and Washington D.C., this is waterfront vacation living designed to be experienced every day. Serenity Lane describes how you feel, not just where you are. Welcome home.

330 Serenity Ln, Chester

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600