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$38,200,000
4 Beds ⋅ 2 Baths
Tulip Forest, a farm defined by scale, stewardship, and long-term value. Recognized as a premier sporting estate, this legacy holding property is the kind of asset that seldom comes to market on Maryland's Upper Eastern Shore. 1,054 +/- acres held intact under one ownership: 680 tillable acres, 272 acres of timber, 5 ponds, 3 impoundments, 26.75-acre wetlands restoration project, 45 acres CRP, a 3.75 mile interior gravel road system, 3 residences, and multiple farm outbuildings. At its center stands Caulk's Field House, circa 1743, a remarkably preserved residence on the ground recognized among Maryland's best-preserved War of 1812 sites. Nearly four miles of farm roads reach every corner of the property, and the ponds, impoundments, and mature timber hold waterfowl, whitetail and countless other game species. Also included beyond the farming operation: 7 acres zoned commercial, additional parcels zoned Village, and four sewer allocations secured along Georgetown Road. A working farm today, with room to grow, suited to farmers, sportsmen, conservation buyers, and investors.

8184 Rock Hall Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$19,900,000
4 Beds ⋅ 5 Baths
Rarely… does such a unique, well-designed, constructed, and maintained world-class equestrian facility grace the international real estate market. Spanning 510 preserved acres, this iconic equestrian estate boasts a rich legacy and unparalleled amenities, including a state-of-the-art equestrian training facility built by B&D Builders, a nationally renowned custom builder. RiverEdge Farm is synonymous with world-class equestrian training, ideally suited to any discipline. The farm has previously housed numerous Olympic dressage and three-day event horses, operated as a top-class private thoroughbred breeding facility, and most recently served as a training mecca for world-class dressage. At the heart of the property is a spectacular 31-stall, 45,000-square-foot indoor dressage show barn. Built with unmatched craftsmanship and old-world charm second to none. Visitors are welcomed through a charming, covered porch and elegant, glass-paneled double doors into a grand reception area featuring a central stone fireplace and a private meeting room, all adorned with custom millwork throughout. Overlooking the 100’ x 200’ indoor dressage arena are stunning glass-enclosed observation areas on both the first and second floors, that are brilliantly filled with natural light and character. This impressive space includes twin service bars, a conveniently located commercial-grade kitchen, and a spacious area ideal for entertaining. An ornate wide-plank staircase leads to a lofted second level with private office suites, an exercise room, and a lounge area. The barn itself is thoughtfully designed, featuring barreled ceilings, six grooming/wash stalls, two well-appointed tack rooms, a central eat-in kitchen/break area, a laundry room, and a three-season sitting room offering panoramic views through grand window walls on two sides. The barn’s layout seamlessly flows through a bank of 31 spacious (mostly 14’ x 14’) stalls, curving into an additional wing with even more accommodations. Complementing the equestrian facilities is a beautifully appointed 9,000-square-foot brick manor home of Georgian architectural style, offering four bedrooms and 3 full & 2 half bathrooms. This wonderful home features an updated kitchen, brick and antique wood flooring, beamed ceilings, a sunken living room, multiple fireplaces, a spacious game room, and a detached three-car garage. The extensive grounds are thoughtfully and professionally landscaped. It artfully blends traditional character with modern conveniences—perfectly suited for today’s lifestyle. Also included within this breathtaking property is a luxurious guest home featuring a chef’s kitchen and an enclosed timber-framed pavilion over a heated indoor pool. Additionally, there is a 15-stall center-aisle block barn with a six-horse Kraft Eurocizer, as well as numerous ancillary operational buildings, including a fully functional brick office building—and numerous double-fenced fields and paddocks with approximately 10 miles of four-rail post-and-board fencing offering unparalleled views throughout the farm. RiverEdge is set within one of Maryland’s largest agricultural preservation areas and is protected by a conservation easement, ensuring its beauty and legacy for generations to come. The property includes 4 parcels: 0802016206 - 109.4 acres, 0802019078 - 186.7 acres, 0802029049 - 106 acres, and 0802029537 - 109.4 acres.

1455 Cayots Corner Rd, Chesapeake City

Listing courtesy of Monument Sotheby's International Realty. Contact: 3026546500
$19,900,000
4 Beds ⋅ 5 Baths
Rarely… does such a unique, well-designed, constructed, and maintained world-class equestrian facility grace the international real estate market. Spanning 510 preserved acres, this iconic equestrian estate boasts a rich legacy and unparalleled amenities, including a state-of-the-art equestrian training facility built by B&D Builders, a nationally renowned custom builder. RiverEdge Farm is synonymous with world-class equestrian training, ideally suited to any discipline. The farm has previously housed numerous Olympic dressage and three-day event horses, operated as a top-class private thoroughbred breeding facility, and most recently served as a training mecca for world-class dressage. At the heart of the property is a spectacular 31-stall, 45,000-square-foot indoor dressage show barn. Built with unmatched craftsmanship and old-world charm second to none. Visitors are welcomed through a charming, covered porch and elegant, glass-paneled double doors into a grand reception area featuring a central stone fireplace and a private meeting room, all adorned with custom millwork throughout. Overlooking the 100’ x 200’ indoor dressage arena are stunning glass-enclosed observation areas on both the first and second floors, that are brilliantly filled with natural light and character. This impressive space includes twin service bars, a conveniently located commercial-grade kitchen, and a spacious area ideal for entertaining. An ornate wide-plank staircase leads to a lofted second level with private office suites, an exercise room, and a lounge area. The barn itself is thoughtfully designed, featuring barreled ceilings, six grooming/wash stalls, two well-appointed tack rooms, a central eat-in kitchen/break area, a laundry room, and a three-season sitting room offering panoramic views through grand window walls on two sides. The barn’s layout seamlessly flows through a bank of 31 spacious (mostly 14’ x 14’) stalls, curving into an additional wing with even more accommodations. Complementing the equestrian facilities is a beautifully appointed 9,000-square-foot brick manor home of Georgian architectural style, offering four bedrooms and 3 full & 2 half bathrooms. This wonderful home features an updated kitchen, brick and antique wood flooring, beamed ceilings, a sunken living room, multiple fireplaces, a spacious game room, and a detached three-car garage. The extensive grounds are thoughtfully and professionally landscaped. It artfully blends traditional character with modern conveniences—perfectly suited for today’s lifestyle. Also included within this breathtaking property is a luxurious guest home featuring a chef’s kitchen and an enclosed timber-framed pavilion over a heated indoor pool. Additionally, there is a 15-stall center-aisle block barn with a six-horse Kraft Eurocizer, as well as numerous ancillary operational buildings, including a fully functional brick office building—and numerous double-fenced fields and paddocks with approximately 10 miles of four-rail post-and-board fencing offering unparalleled views throughout the farm. RiverEdge is set within one of Maryland’s largest agricultural preservation areas and is protected by a conservation easement, ensuring its beauty and legacy for generations to come. The property includes 4 parcels: 0802016206 - 109.4 acres, 0802019078 - 186.7 acres, 0802029049 - 106 acres, and 0802029537 - 109.4 acres.

1455 Cayots Corner Rd, Chesapeake City

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

27 Old South River Rd, Edgewater

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

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

3366 Belmont Ave, Glyndon

Listing courtesy of Monument Sotheby's International Realty. Contact: 4437087074
$16,500,000
7 Beds ⋅ 10 Baths
Set in the heart of Maryland’s storied Worthington Valley, Sagamore Farm offers an extraordinary opportunity to own one of the most iconic estates in American Thoroughbred racing. Founded in 1925 by Isaac Emerson and later entrusted to Alfred G. Vanderbilt Jr., Sagamore rose to international prominence as a premier breeding and training ground, producing legendary racehorses and hosting generations of equestrian excellence. Today, the estate spans over 524± acres of rolling pastures framed by classic white board fencing, thoughtfully restored to honor its legacy while supporting modern operations. At its center, a stately 16,000+ square foot residence offers gracious, light-filled living spaces designed for both refined entertaining and everyday comfort. A richly appointed library provides a quiet retreat, while the formal dining room, scaled for memorable gatherings, sets the stage for elegant evenings. Each of the six upper-level bedrooms features its own en-suite bath, creating a private sanctuary for family and guests alike. The equestrian facilities are equally exceptional. A 3/4-mile (six-furlong) Tapeta synthetic training track delivers superior footing, complemented by the iconic Clocker’s Tower with a viewing lounge, kitchenette, and dining area offering an elevated vantage point for overseeing training or hosting with ease. The property includes a comprehensive collection of barns, including a stallion barn, training barn, broodmare barn, and foaling barn, along with expansive turnout paddocks. Vanderbilt's original home remains on the property, providing residence for a general manager, while the well-appointed bunkhouse provides comfortable accommodations for staff and jockeys. Also on the grounds is an historic natural spring house, adding a distinctive nod to the land’s enduring heritage. With its unmatched pedigree, world-class infrastructure, and timeless setting, Sagamore Farm represents a rare offering equally suited for a premier Thoroughbred operation or a visionary expansion into additional equestrian disciplines. A legacy property of remarkable scale, significance, and possibility. With effortless access to I-83, I-695, BWI Airport, Washington, D.C., New York, and central to the world’s most prestigious racing venues, Sagamore Farm stands ready for its next chapter.

3366 Belmont Ave, Glyndon

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

19700 Mulberry Fields Rd, Leonardtown

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

$13,750,000
5 Beds ⋅ 9 Baths
Stock Range Farm spans 350 acres of prime waterfront and is available for purchase in its entirety OR with reduced acreage including the main residence, if the buyer so chooses. Options include selling main residence with 20+ acres, 40+ acres, and 100+ acres. **CALL listing agent for more information! The property is free of easements and includes development rights, subject to all applicable Talbot County zoning regulations. With vast working farmland and resort-style amenities, this rare gem truly combines luxury and sophistication with seclusion and tranquility. The 12,000+ sq. ft. primary residence showcases the breathtaking stylings of acclaimed architect Peter Jay Zweig and exemplifies the pinnacle of luxury living. Built by Ilex Construction, striking architectural details and unparalleled craftsmanship are demonstrated throughout, seamlessly integrating with the breathtaking beauty of the landscape. This magnificent home is filled with an abundance of natural light and boasts panoramic views, thanks to soaring glass walls that overlook the tranquil waters of Pickering Creek, expansive fields, and picturesque vineyards. The thoughtfully curated interior includes spacious living areas, a stunning owner's wing that offers privacy and comfort, and a separate guest wing that features a full kitchen, providing ideal accommodations for family and visitors. High-end features abound, including a gourmet kitchen, recreation room complete with kitchen and bar for entertaining, full exercise room, 5 car garages, elevator, heated limestone floors, Venetian plaster walls, and multiple outdoor decks. At every turn, this property exudes the loving care it has received. Outside, the resort-style amenities include a large, heated infinity pool, complete with waterfall and hot tub, stunning pool pavilion with full outdoor kitchen, stone fireplace, and two TV’s and AV system. Along with the waterside tennis/pickleball court, tranquil koi pond, and private pier with 4-5’MLW, the opportunities for outdoor fun and relaxation are boundless. In addition is the beautifully renovated 4-bedroom guesthouse with views of the vineyards, providing comfortable accommodations for family and friends. A well-equipped 9-stall barn includes a tack room/office, kitchenette, and a riding ring, complemented by 20 acres of fenced pastures. There is also a 3-4 BR caretaker's home, a fully outfitted greenhouse, large equipment barn complete with an office and full workshop, and hay barn for storage. The property also offers excellent hunting opportunities, making it a versatile retreat for outdoor enthusiasts. The highlights of this extraordinary property continue through every acre, including sweeping landscapes and hardscapes, 200 acres of working farmland, 5 acres of vineyards, and a 6-acre stocked pond with private island. Unparalleled in its mix of tranquility and luxury, the opportunity to experience the very best of the Eastern Shore’s refined lifestyle and natural beauty is only possible at Stock Range Farm. Please don't drive in driveway as there are security cameras and alarm. All appointments must be made with listing agent and additional information and details are available upon request.

27772 Sharp Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$12,975,000
6 Beds ⋅ 11 Baths
This extraordinary gated 20-acre waterfront estate, featuring a French-inspired stone residence, sits prominently along the banks of the Severn River just minutes from downtown Annapolis and under an hour from Washington, DC. With coveted western exposure, the property offers breathtaking, year-round sunsets and over 23,000 square feet of combined living space across the main house, guest house, and carriage house—all set amid rolling lawns, formal gardens, mature trees, and natural surroundings. The main residence is designed for both grand entertaining and comfortable living, with ten sets of French doors opening to terraces and gardens. A dramatic two-story foyer with limestone and marble inlays leads to a soaring great room anchored by an 18th-century French carved limestone mantel. Additional main-level spaces include a formal dining room, library, and music room—each with its own fireplace—and a gourmet kitchen featuring dual marble-topped islands. Upstairs, an open gallery overlooks the great room and grounds, while the expansive primary suite offers a fireplace, private sitting room, and waterside balcony with sweeping river views. The lower level is equally impressive, with a family room, billiards room and bar, a striking stone wine cellar with tasting room, media room, full gym with bath and sauna, and an additional bedroom suite. A separate wing provides a dedicated art studio or craft space, complemented by a motor court and two three-car garages. Outdoor living is equally refined, with manicured lawns and gardens, an expansive patio, outdoor kitchen, hot tub, and charming details including a gardening shed, chicken coop, and raised beds. The approximately 6,000-square-foot guest house is ideal for hosting, centered around a pool with a covered veranda, outdoor fireplace, bar, and gazebo—all with water views. Inside, it offers spacious living and dining areas with a shared stone fireplace, three bedrooms, two full and two half baths, and a full catering kitchen with Viking appliances. A breezeway connects to the carriage house with an additional three-car garage. The estate’s 900 feet of shoreline is complemented by a 350-foot deep-water pier (8–9' MLW) with four slips, including two accommodating 60-foot vessels, and two boat lifts—perfect for boating, sailing, and enjoying life on the Severn River and Chesapeake Bay.

938 Old County Rd, Severna Park

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$12,500,000
5 Beds ⋅ 7 Baths
A rare opportunity on Spa Creek, this fully reimagined Murray Hill residence offers an extraordinary waterfront lifestyle just moments from downtown Annapolis. Completed in late 2023 after a full ground-up rebuild, the home spans 5,900+ sq. ft. of impeccably crafted living space, where natural materials, refined architectural details, and top-tier systems create a seamless blend of comfort and sophistication. Set on just under a half acre of level waterfront, the property showcases one of the most complete private pier systems in the area: a heavily built main pier, two floating docks, and three boat lifts (16,000lb, 8,000lb, and 2,500lb), plus lighting, water, 30/50-amp shore power, Tide Slide moorings, and 6' MLW at the 70' T-head. A charming boathouse and waterside deck capture the magic of Spa Creek from morning to sunset. Outdoor living is exceptional. A stunning 40' x 20' PebbleTec saltwater pool—rebuilt in 2024—anchors a series of Ipe decks and natural stone patios and decks designed for effortless entertaining. The outdoor kitchen with piped natural gas grill, refrigerator, and sink extends gatherings well into the warm months, while covered and uncovered spaces offer year-round enjoyment. The exterior speaks to enduring quality with Carderock stone foundations, mahogany trim and ceilings, Loewen windows, Canadian cedar siding, copper gutters and flashings, and custom mahogany entry doors. A detached heated and cooled two-car garage includes a beautifully finished upper level with kitchenette, laundry, living/sleeping area, and private bath—ideal for guests or an au pair. Inside, the home is defined by warm natural luxury featuring a stunning barrel vaulted mahogany ceiling with cove lighting. Additional curated details include: mahogany doors, black bronze hardware, 5" Cumaru flooring, custom cabinetry, and extensive millwork throughout. The chef’s kitchen features Sub-Zero and Wolf appliances with granite and soapstone surfaces. The main level Primary suite with inspiring view of pool and waterfront provides convenience and options for aging in place. The lower-level recreation spaces provide a relaxed retreat with a private bedroom suite, family room, wet bar, gym and full laundry room. An abundance of thoughtful design is presented throughout the home with multiple wet bars, radiant heated tile floors in five bathrooms and the main-level bar, and four separate laundry areas. Less than half a mile from Church Circle, this residence delivers the rare ability to live on the water while enjoying the full walk-everywhere lifestyle of historic Annapolis. This is Spa Creek living at its finest: sophisticated, effortless, and undeniably special. Welcome Home!

5 Franklin St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$12,000,000
3 Beds ⋅ 2 Baths
124 +/- acres on the edge of Easton Md town limits. Farm is currently in row crop production. Situated between Matthewstown Run and Waylands subdivisions, this property is ideal for development potential located in priority areas two and three of Easton's Comprehensive Plan Growth Map. BUYER'S RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

29587 Matthewstown Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$11,995,000
4 Beds ⋅ 5 Baths
Private Island at 1546 Teal Drive, Ocean City, Maryland is a truly unique offering — the bay's only island estate. Included is an adjacent buildable waterfront lot just inside the entrance gates before crossing the private bridge. The improved .29-acre parcel features approximately 95 feet of bulkheaded shoreline with boardwalk, paved driveway, irrigation, and landscaping, offering flexibility for a future guest house or single-family residence, additional parking, or expanded waterfront enjoyment. Located off 15th Street in downtown Ocean City, the property offers seclusion and accessibility, 3 blocks to the Boardwalk and beach, minutes to the Ocean City Inlet and Assateague Island by boat, and a block from Harbor Island, home of the world-renowned White Marlin Open. Hidden behind a brick wall and accessed through a 6-foot gate, the arrival continues across a private 120-foot vehicular bridge from Mallard Island. The island encompasses more than 3 acres of native marshlands and coastal landscape with panoramic views of the open bay, the Rt. 50 Bridge to the south, Rt. 90 Bridge to the north, and the rare combination of breathtaking sunrises and sunsets across the water. Architecturally, the home is an iconic shingle-style residence inspired by Nantucket architecture, with exterior renovations and enhancements by renowned Lyman Perry Architects Ltd. of Nantucket, Massachusetts. The approximately 5,000-square-foot home features custom woodworking, Carlisle wide-plank hand-finished pine flooring, new Andersen doors throughout, approximately 3,250 square feet of wraparound decking, and expansive water views. Upon entering, a dramatic 24-foot atrium features a 12-foot by 15-foot overhead skylight and floor-to-ceiling Coral Rock fireplace feature connecting the surrounding living spaces. Designed to maximize open bay views throughout, the main living area features custom built-in cabinetry and flows into the separate dining and gathering spaces. The kitchen/family room creates an inviting area for entertaining, with custom solid birch painted cabinetry by Premier Cabinetry of New Holland, Pennsylvania, and a 5-foot by 8-foot teak island countertop. A custom wood spiral staircase provides secondary access between the main and upper levels. The main level also includes a home office with built-in cabinetry and pull-out file storage, plus an additional guest bedroom and full bath. Upstairs, an open bridge hallway overlooks the atrium while separating the primary suite from two guest bedroom suites. The four-room primary suite includes a bedroom retreat with bayfront deck, sitting/entertainment/dressing room with vaulted ceilings, custom cherry wood built-ins and four closets, en-suite bath with double vanity and dressing table, and a second dressing room with vaulted ceilings, four double-door deep closets, and an arched window with window seat dividing two built-in tall chests. Two additional bedrooms each feature en-suite baths and private decks. Outdoors, an island retreat features a pool and spa by Sea Glass Pools, expansive decking, gazebo bar with cabinetry and quartz countertops, full bath with shower, docking, 10,000-pound boat lift, and fish cleaning station. Significant recent investments include bulkhead improvements, reinforced helical pilings, bridge renovations, active security and surveillance systems, and maintained structural and mechanical systems. Surrounded by abundant birdlife and endless open-water vistas, this distinguished estate embodies timeless elegance.

1546 Teal Dr, Ocean City

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

933 Hillside Lot A, Lutherville Timonium

Listing courtesy of Krauss Real Property Brokerage. Contact: (410) 804-7921
$11,700,000
6 Beds ⋅ 9 Baths
Live authentically. Align forces with the internationally renowned designer Steven Gambrel. Cultivate your vision with a designer who draws inspiration from vernacular architectural details of the region and was honored as one of “today’s greatest talents in Architecture and Design” in Architectural Digest’s “AD 100.” A true artist and masterful conductor of form. Steven subscribes to the importance of properly proportioned structures and details, partnered always with a carefully curated collection of vintage, antique, and custom furniture designed by Steven himself. Embark on a journey to create a destination for you and your family. Enduring architecture and honed materials give you the experience of feeling settled and inspired all at once. The award-winning Delbert Adams Construction Group is here to help you realize your vision in all its brilliance. This 20-acre site is worthy of a legacy estate. Raw in its current state, awaiting to be shaped by new stewards. Two separately deeded building sites exist. Elevated main estate site overlooking idyllic pond teeming with life. Relish the long treelined drive with iconic old stone entry monuments. Glorious private setting. Ample room for pool, guest house, gardens, greenhouse, tennis courts, and whatever else might be on your mind. Rock outcroppings. Ponder the benefits of building exactly what you desire. Lively meandering stream and walking paths. Unleash your vision for living with an incredibly talented team to get you there. A site where the synergy of your creativity is elevated with the land. Tucked away in the heart of Greenspring Valley. One of the few sites left in the Valley. Incredibly accessible to Falls Rd, 83, and 695. Conservation easement exists. Photos are concepts for inspiration. Please do not visit the property without an appointment. The art of uniting human and home. Please see related listings. The seller is doing some site work and we will be back in the fall: Hillside | Land | MLS# MDBC2007018 933 Hillside Rd | Land | MLS# 1000113931- Temp off 933 Hillside Rd | Land | MLS# MDBC2026716 -Temp off 933 Hillside Lot A | Residential | MLS# MDBC2026352- Temp off 933 Hillside Lot A | Farm | MLS# MDBC2026534

933 Hillside Lot A, Lutherville Timonium

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

8 Spa View Cir, Annapolis

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

29245 Howell Point Rd, Trappe

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

3344 Harness Creek Rd, Annapolis

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

Glyndon

Listing courtesy of Krauss Real Property Brokerage. Contact: (410) 804-7921
$10,200,000
7 Beds ⋅ 7 Baths
Live authentically. Magnificent stone estate tucked away overlooking Worthington Valley and beyond. Upper Melinda awaits perched on 235.00+/- acres. Commanding views of the valley complement the strength grandeur of this enduring architectural masterpiece. Relish the meandering drive home through lush woodlands. A sanctuary of tranquility and serenity. Crafted by acclaimed architect Louis McLane Fisher and adorned by the legendary Baltimore native, Billy Baldwin. Discover the whispers of Baldwin’s timeless touches lingering in dashes of red lacquer accents and smokey mirrors throughout. Within, nine roaring fireplaces beckon conversation and radiate comforting warmth. Main level owner’s suite. Transform your nocturnal journey as you gaze across the valley before falling into restful slumber. Your inner chef will flourish in the cooking space. Partake in lighthearted fun and competition in the basement game room. Original cork flooring embellished with exotic animal inlays; intact. Immerse yourself in the opulence of rich landscaping as you explore your outdoor haven. Savor the stillness and go for an invigorating round of laps in the sublime pool.. Recharge in the ambiance. An expansive stone terrace embraced by abundant greenery beckons for an elevated outdoor dining experience. Other worldly views that are hard to grasp. A palpable depth of wonder permeates. A sensory experience. Vistas that mirror paintings. Gaze over glistening ponds in the distance. Truly a living canvas from which to paint the next chapter of your life. A legacy property. 5 +/- miles of extensive trail network throughout the grounds. Revel in the extreme privacy. Indulge in the vast beauty that unfolds around you. Enchanting stone guest house recently renovated. Four income generating tenant houses convey that are unable to be divided. Cultivate your existence. The art of uniting human and home. Do not drive to property without an appointment. Property is subject to conservation easement.

Glyndon

Listing courtesy of Krauss Real Property Brokerage. Contact: (410) 804-7921
$10,000,000
14 Beds ⋅ 14 Baths
This offering marks an extraordinary opportunity to acquire one of North America’s most prestigious properties. While the 437.5 acre farm is globally celebrated for its history of breeding, training, and raising excellence and many world-class sport horse champions, the focus now turns to the sale of the physical estate, a masterpiece of equestrian infrastructure and natural beauty now available for its next chapter. The property is defined by its remarkable landscape, featuring 200 wooded acres of mature trees, 220 acres of pastureland, and 15 acres of impervious structures across the gently rolling terrain of Cecil County. Bordered by 1.3 miles of tranquil waters of the Octoraro Creek, the land offers a rare combination of high-performance utility and serene privacy. The sale includes comprehensive, established equestrian infrastructure, highlighted by a 36-stall main barn, 2 outdoor arenas, 12 fields, 31 paddocks, 14 dwellings, 2 additional barns, and numerous equine facilities that have served as the benchmark for elite sport horse development for decades. The true value of Hilltop Farm’s footprint lies in its versatility; it is a canvas limited only by the scale of one’s imagination. While its equestrian pedigree is unrivaled, the estate invites a bold repurposing as a world-class Agri-Tourism Destination or a Private Legacy Compound. The riverfront and woodlands are perfectly suited for a Luxury Wellness Retreat, with riparian trails just a stone's throw from the urban corridors of Philadelphia, Baltimore, and DC. As this historic operational chapter concludes, the property is now positioned for a new curator to inherit a landscape of immense function and beauty. This is a rare chance to own a sanctuary that has been both a stage for international sport and a community standard-bearer. This property includes multiple parcels and should be referenced in conjunction with MLS# MDCC2020402 (Tax ID: 0806025811) and MLS# MDCC2020404 (Tax ID: 0806012450). 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: (443) 292-6767
$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 listing includes multiple parcels and should be referenced in conjunction with MLS# MDCC2020400 and MLS# MDCC2020404. Photos #6, #9, #12, #18, #30, #32, #40, #52, #59, #63, #68, #70, and #83 are AI-generated concept images of the Conference Center, Tenant House, and Lodge and are intended for illustrative purposes only.

1089 Nesbitt Rd, Colora

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$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: (410) 280-5600
$9,950,000
5 Beds ⋅ 10 Baths
Live authentically. Sunny Hill Farm circa 1937. Brilliantly designed by William McMillan, storied architect. McMillan was also commissioned locally to design Alfred Vanderbilt's residence at Sagamore. McMillan married Grace G. Roosevelt, granddaughter of Theodore Roosevelt. They lived their days out at Sunny Hill. This is the second time it has been offered. A significant estate perched on 261 glorious acres with spectacular panoramic views of Worthington Valley. Masterful architecture. This English Country estate was sited in a way that dances with the sun. Your sense of arrival is punctuated by a very purposeful Moon Gate. I can only imagine an architect who is just as avid of a yachtsman would incorporate such a feature to connect with a framed view of the cosmos. Remarkable. Poetic interior and exterior courtyards grace every space. Soothing fountains are placed just so. Artistically framed views abound. Dazzling use of expansion and contraction. Sunny Hill will have a profound effect on you. A place to be cherished for generations. A cultivated trail network exists... adventure through vast woodlands, streams, orchards, and rolling farmland. You will experience microclimates from one end of the property to the other. Teeming with wildlife. Stroll seamlessly into the great outdoors and never miss a sunrise or sunset from one of your many terraces. Exquisite pool and hot tub. Ample space to curate pasture and equestrian facilities if desired. Greenhouse. Amish built five bay barn. Additional potential densities. Cultivate your existence. The art of uniting human and home.

3600 Butler Rd, Glyndon

Listing courtesy of Krauss Real Property Brokerage. Contact: (410) 804-7921
$9,950,000
5 Beds ⋅ 10 Baths
Live authentically. Sunny Hill Farm circa 1937. Brilliantly designed by William McMillan, storied architect. McMillan was also commissioned locally to design Alfred Vanderbilt's residence at Sagamore. McMillan married Grace G. Roosevelt, granddaughter of Theodore Roosevelt. They lived their days out at Sunny Hill. This is the second time it has been offered. A significant estate perched on 261 glorious acres with spectacular panoramic views of Worthington Valley. Masterful architecture. This English Country estate was sited in a way that dances with the sun. Your sense of arrival is punctuated by a very purposeful Moon Gate. I can only imagine an architect who is just as avid of a yachtsman would incorporate such a feature to connect with a framed view of the cosmos. Remarkable. Poetic interior and exterior courtyards grace every space. Soothing fountains are placed just so. Artistically framed views abound. Dazzling use of expansion and contraction. Sunny Hill will have a profound effect on you. A place to be cherished for generations. A cultivated trail network exists... adventure through vast woodlands, streams, orchards, and rolling farmland. You will experience microclimates from one end of the property to the other. Teeming with wildlife. Stroll seamlessly into the great outdoors and never miss a sunrise or sunset from one of your many terraces. Exquisite pool and hot tub. Ample space to curate pasture and equestrian facilities if desired. Greenhouse. Amish built five bay barn. Additional potential densities. Cultivate your existence. The art of uniting human and home.

3600 Butler Rd, Glyndon

Listing courtesy of Krauss Real Property Brokerage. Contact: (410) 804-7921
$9,500,000
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:

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

12903 Windy Dr, Ocean City

Listing courtesy of Holiday Real Estate. Contact: 4105247700
$8,995,000
7 Beds ⋅ 10 Baths
7112 Natelli Woods Lane, a stately new construction designed by GTM Architects. Envisioned as a seamless union of timeless elegance and modern luxury, this 13,000+ square foot estate rests on two sweeping acres of manicured landscape. A striking all-glass and steel pivot front door leads into a dramatic foyer, flanked by a formal study and grand dining room. The interiors are defined by bespoke finishes, including 9-foot Barausse Italian doors throughout, custom Italian cabinetry by Stossa Metropolis in the kitchen and bar, and meticulously tailored closets by ARAAN of Italy. The heart of the home—an exquisite chef’s kitchen with Miele appliances—flows effortlessly into a soaring family room with 22-foot ceilings, setting the stage for refined entertaining. Ambiance is perfected by a state-of-the-art Lutron lighting system, offering over 15 million combinations, paired with custom automated Lutron shades. A butler’s pantry, scullery, elevator, and stylish powder room add convenience. The main level features a lavish primary suite retreat with a spa-inspired bath, sitting room, and access to a covered porch. Additional highlights include a laundry room, pool bath, and five-car garage. A 30'x15' covered porch with arches, columns, heating, and a dual-sided fireplace invites all-season enjoyment with a view of the pool beyond. Upstairs, discover five secondary bedroom suites, an optional second primary suite, and a sunlit family lounge overlooking the grounds. The fully finished lower level is designed for indulgent recreation with a cinema, bar lounge, golf simulator, gym, billiards area, and a private guest suite.

7112 Natelli Woods Ln, Bethesda

Listing courtesy of TTR Sotheby's International Realty. Contact: 2029750873
$8,995,000
6 Beds ⋅ 5 Baths
Set on 93 private acres with 6,100 feet of shoreline along the picturesque Sassafras River and Cox Creek. The estate includes a main house, guest house, pool house and riverside pavilion, offering ample delightful space for large groups to gather, unwind and experience the activities and natural beauty of the upper Chesapeake. Showcasing exceptional design, materials, craftsmanship, the living spaces are framed by expansive views of the Sassafras River. The main residence includes six spacious bedrooms and four and a half baths. The heart of the home is a gourmet kitchen and adjacent generous breakfast room wrapped in 180-degree river views, a setting that enhances every meal. The home flows naturally into multiple large gathering spaces built for entertaining, and into quieter, more intimate rooms designed for reflection and rest. The guest house ensures that you can accommodate family and friends. With three generously sized bedrooms and one and a half baths, full kitchen, fireplace and brick patio, it offers a self-contained retreat that gives guests their own space while keeping everyone together on the estate. The pool complex redefines what a backyard amenity can be. At its center is a 52,000-gallon swimming pool with a retractable electric cover, positioned to frame sweeping panoramic river views. An adjoining heated spa and a oversized pool deck complete a setting that invites long, unhurried afternoons in the sun. Elevating the experience further, it offers a full bath, generous living and dining areas, and amenities more commonly found at a high-end resort - a large, well-equipped gym and an eight-person steam room -providing the perfect end to an active day. Perched at the water's edge, the recently constructed two-story pavilion is the social and recreational heart of the estate's waterfront. It's a front-row seat to everything that makes the Sassafras River so beloved: working crab boats in the early morning, sailboats gliding past at midday, and the sky turning gold over the water at dusk. Spend a lazy afternoon on the pavilion's upper level as the river life unfolds below, then head down to launch your own boat from the private boat lift or boat ramp. The Sassafras and Cox Creek offer boundless activities including boating, water skiing, tubing, wakeboarding, sailing, paddleboarding, and kayaking, all awaiting just steps away. After fun on the water, return to the pavilion for lunch, dinner, or simply a seat with one of the best views on the upper Bay. Adjacent to the grassy wharf, the nearly 1,000-foot private sandy beach is a rare and remarkable amenity ideal for an afternoon stroll with friends or a quiet moment watching the sunset or moon rise over the river. Other improvements along the waterfront include a 1000+ stone revetment protecting the shoreline, a 13,000lb boat lift, and a boat ramp. The grounds reflect a thoughtful balance of beauty, privacy, and long-term stewardship, with carefully planned enhancements designed to complement the natural setting while supporting comfortable estate living. Mature trees and established landscaping create a sense of arrival and continuity across the property, while curated sightlines and open lawn areas transition naturally into wooded edges and surrounding countryside. A network of trails invites exploration through the woods, offering quiet vantage points and seasonal changes that reinforce the property’s connection to the Eastern Shore landscape. The property's blend of fields, woods and waterfront habitats, complemented by offshore hunting rights offers productive hunting. The land supports healthy populations of deer, wild turkey, ducks & geese, creating a sportsman's haven throughout the seasons. Enjoy fishing and crabbing from the dock ideally located on the edge of the deep water channel. Major mid-Atlantic cities, international airports & train stations are within easy reach, making the estate accessible for full-time residents and weekend escapes.

750 Cassidy Wharf Rd, Earleville

Listing courtesy of Gunther-McClary Real Estate. Contact:

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

964 Taylors Island Rd, Madison

Listing courtesy of National Land Realty, LLC. Contact: 4434128971
$8,950,000
24 Beds ⋅ 13 Baths
Parsons Creek Farm - A 255+/- Acre, Multi-Residence, Deep-Water, Waterfowl & Wildlife Estate at the Confluence of Parsons Creek and the Little Choptank River This once-in-a-lifetime Chesapeake Bay legacy holding is set upon 255.47 extraordinary acres of waterfront, wetlands, upland forest, and meticulously curated wildlife habitat making Parsons Creek Farm one of the most sophisticated private estates on Maryland's Eastern Shore. Masterfully blending historic charm, modern craftsmanship, high-performance land management, and recreational luxury, this turnkey, multi-residence compound stands unrivaled in scale, ecological design, and architectural execution. Positioned at the union of Parsons Creek and the Little Choptank River, the property enjoys nearly a mile of sandy, private shoreline, deep-water access, expansive water vistas, and complete seclusion - yet remains within a short drive to Cambridge, Annapolis, Baltimore, Washington, and the greater Mid-Atlantic corridor. A series of thoughtfully positioned structures - each with its own architectural identity - combine to create a private compound capable of sleeping more than 24 guests in total comfort. Elegantly sited to capture uninterrupted views across impoundments, woodlands, and water, the primary residence blends historic Maryland character with refined luxury. This meticulously designed, 9,583 sq. ft. luxury residence boasts an impressive array of distinct living areas, creating a home of both grand scale and exceptional comfort for family living and entertaining. The expansive property also features a charming, fully renovated, private 1,500 sq. ft. Cape Cod–style guest house that extends a warm welcome to visitors, and a third two-story residence complete with a full bedroom suite, full bathroom, laundry, and sweeping picture windows overlooking one of the ponds. Part of the estate's recreational opportunities is an over-the-water bar and game room, a gathering place where family and friends can cast a line into the pond while enjoying the comforts of a private lounge. Equestrian enthusiasts and entertainers alike will appreciate the impressive stable complex, complete with second-floor luxurious living quarters, a spacious game room, and full bar. Balconies at each end capture sweeping views of the surrounding woodland and water, creating an atmosphere of timeless elegance. Whether envisioned as a generational family compound, a private sporting estate, a conservation-forward investment property, or an exclusive corporate/hospitality retreat, Parsons Creek Farm offers a combination of luxury, ecological engineering, and rural waterfront beauty unmatched anywhere in the Mid-Atlantic. This remarkable waterfront estate is a unique opportunity that unites world-class waterfowl and upland hunting, meticulous wildlife management, and refined living—enhanced by impressive income potential. Having identified his replacement property, the seller is prepared to move forward and welcomes qualified offers.

964 Taylors Island Rd, Madison

Listing courtesy of National Land Realty, LLC. Contact: 4434128971