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$3,100,000
4 Beds ⋅ 4 Baths
Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining options. There is a gorgeous gourmet kitchen complete with quartz counters, stainless steel appliances and walk in pantry, seamlessly flowing into a spacious family room with a timeless double sided brick fireplace and built-in bookcase. An architecturally stunning screened octagonal porch—perfect for relaxing or entertaining. A brick-floored sunroom with gas fireplace and pool bath leads to an expansive patio overlooking the waterside pool, framed by a rock waterfall, and custom gazebo. The luxurious primary suite features cathedral ceilings, French doors leading to the sunroom and a spa-inspired bath with walk in tile shower and soaking tub. Two additional en-suite bedrooms, a large den with custom built-ins perfect for library or additional bedroom, and a spacious butler’s pantry with granite counters, extra refrigerator, stainless sink and additional cabinetry. A separate study and conditioned workshop offer versatile space. Set on five beautifully landscaped acres with southern exposure, the property boasts 370+/- feet of protected shoreline and a 350-foot private pier with 6 feet of deep water. Boating enthusiasts will appreciate the 15,000-lb and 8,000-lb lifts, two additional slips, and a floating dock. A gated 30' x 40' flower/vegetable garden with raised beds, an oversized 2-car garage and large garden shed complete this beautiful home. Septic is for 3 BR but office could be BR #4.

23961 Lynnewood Dr, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$1,679,000
4 Beds ⋅ 4 Baths
Significant price improvement! Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square feet, all on the main level, the home is designed for convenience and ease of living. Inside, generous rooms are enhanced by rich custom yellow pine floors, premium carpeting, and tile. At the heart of the home, the living room impresses with a vaulted ceiling, exposed beams, custom built-ins, and a rustic wood-burning fireplace. A waterfront family room flows into the dining area, while the country kitchen features handsome cabinetry, premium countertops, modern appliances, and a pantry with washer and dryer. The waterside primary suite offers a fireplace, walk-in closet, and a spacious bathroom with dual vanities. On the opposite side of the home, a second bedroom includes an ensuite bath and walk-in closet, complemented by two additional bedrooms with ample closet space (one used as den) and a full bath. The exterior showcases cedar shake siding, a welcoming covered front porch, a private patio between the main bedrooms, a large rear waterside deck, a two-car detached garage, and a wide gravel driveway with ample guest parking. The property is served by a private well and septic system, with public sewer hookup approved and coming soon, offering flexibility for future expansion or renovation. This home is part of a unique five-property HOA (fees $600/year) with each property owning 20% of a central community lot, a deepwater dock with five slips, and a historic pavilion available for member events and leisure. Residents also enjoy a kayak rack and a small sandy beach for launching boats or paddle boards. The setting provides not only a comfortable home but a lifestyle of Chesapeake Bay waterfront living. According to research, the grounds of the five lots and the “Oakwood Association” belonged long ago to the Oakwood Inn, a prominent retreat in the early 20th century. Known for its scenic harbor views and role in local leisure culture, the inn appeared in postcards from the 1930s and was a hub for skating, swimming, pleasure boating, regattas, and log canoe races. Its legacy adds a rich historical dimension to the property, connecting today’s residents to St. Michaels’ vibrant past as a sailing and leisure destination. There are photos of two pieces of memorabilia at the end of the photo section of this listing for your enjoyment. See attached documents for HOA information ($600/year per property), easement information, C&Rs, Contract Disclosures, etc. Flood Zone X, no flood insurance required. Three-bedroom septic, public sewer hookup available near future.

24390 Oakwood Park Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$3,999,900
4 Beds ⋅ 7 Baths
Swan Point is an exquisite waterfront estate set on approximately 4.5 acres, offering sweeping westerly views across the Tred Avon River. A gated, paved driveway with cobblestone curbs welcomes you to this private retreat. This stately Colonial features 4 bedrooms, 4 full baths, and 3 half baths, thoughtfully designed for both intimate living and grand entertaining. The formal living room, complete with a wood-burning fireplace, opens to a charming three-season porch. A separate formal dining room provides an elegant setting for gatherings. The gourmet kitchen includes a breakfast area and adjoining den with a wood-burning fireplace and 600-year-old heart pine floors that are radiant-heated. A spacious sunroom extends from the kitchen and flows seamlessly onto a brick patio with a built-in grill and is just steps from an inground, heated pool with spa and brick surround. A separate laundry room with powder room, and an attached two-car garage finish off the main level. The partially finished basement offers additional living space with a wood-burning fireplace, full kitchen, and powder room. A private staircase leads to the primary suite, located in its own secluded wing, featuring two walk-in cedar closets and a luxurious bath with soaking tub and separate shower. The main staircase leads to additional bedrooms, including a second primary suite, a third bedroom with hall bath, and a fourth bedroom with a sitting room and en suite bath. Outdoors, a large dock with seating area offers approximately 4’ MLW, water, electric, and two boat lifts. The partially rip-rapped shoreline enhances both beauty and stability. The spacious carriage house includes room for collector cars, an office with gas fireplace and wet bar, a conference room or flex space, and a powder room. A three-car detached garage offers additional storage with a guest apartment above. Equestrian enthusiasts will appreciate the barn with four stalls, office, tack room, and abundant loft storage, along with three paddocks for horses. A workshop with wood stove and powder room provides the perfect space for woodworking or creative pursuits. A second entrance offers convenient access for horse trailers or boats. Swan Point combines timeless elegance, comfort, and versatility—all set against one of the Eastern Shore’s most captivating waterfront backdrops. Easton, Maryland, known as the New Hamptons of the Chesapeake Bay by Forbes Magazine, is conveniently located 1.5 hours from D.C. and Baltimore, and 2 hours from Philadelphia. Just minutes from fine dining, shopping, healthcare, theatres, galleries, museums, golf courses, a country club, a yacht club, and a jet airport.

27473 Westpoint Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$499,990
4 Beds ⋅ 3 Baths
Enjoy the serenity of country living just minutes from both downtown Easton and Cambridge! This spacious four bedroom, two and a half bath home offers over 3,400 square feet of living space and sits on nearly an acre (.96+/-) with covered front porch and nice rear deck with views of open fields/farmland. This solid house offers a comfortable layout on both levels and it's perfect for both everyday living and entertaining. The main level features a large two story foyer with beautiful staircase, large family room, open kitchen with breakfast nook and beautiful bay window, separate dining room, and sunroom with vaulted ceiling, skylights, wood burning fireplace and beautiful open views of farmland. Upstairs, the primary suite is like a private retreat with it’s own bathroom, walk in closet and balcony. Three additional bedrooms and bath complete the second floor. Attached two car garage with private circular drive surrounded by mature trees for privacy. The home features a new roof (2025), a new well, new septic system (2025) and new HVAC (2022). Within a mile of Ferry Point Marina, Waterfront State Park and Choptank Fishing Pier. Close to all of downtown Trappe/Easton/Cambridge shopping, restaurants, churches and medical facilities.

2669 Ocean Gtwy, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$2,995,000
4 Beds ⋅ 4 Baths
Absolutely stunning mid-century contemporary estate offering a private , park-like setting, with heated swimming pool, pavilion, luxurious fully equipped outdoor- kitchen, outdoor shower, in -ground hot tub ,tennis court, and maintenance -free Azek pier with new 30K lb. boat lift. Meticulously maintained inside and out! Professionally landscaped with WiFi controlled front/rear irrigation system.The superbly designed and crafted home offers an open floor-plan with 4 bedrooms and an office, 3.5 designer baths with heated floors,, a magnificent gourmet kitchen, upper and lower level living areas providing outstanding functionality. Breathtaking water- views and protected shoreline! This is an outstanding turn-key property that comes beautifully furnished !

5837 Irish Creek Rd, Royal Oak

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

$3,700,000
5 Beds ⋅ 7 Baths
GENEROUS PRICE REDUCTION!!!! This remarkable property has it all. Private 15 plus acres. Beautiful views overlooking Dunn's Cove sunrises. A shore sportsman's dream. Partially wooded, fields of crops, hunting blind and a pier for your fishing vessel. This was a large compound with the Main house, in-law wing and a separate 2 BR guest house w/fireplace and large screened porch. Waterside in-ground pool and children's play area. Large garage/barn to store all the water toys and pool equipment. It's currently being used as a Vacation Rental. Showings will be staggered between use.

21721 Heavenly Haven Rd, Sherwood

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$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
$995,000
Rare find, prime Bailey's Neck/Easton location. This beautiful 3+ acre waterfront lot is on the Tred Avon River in the highly sought after Oxford Corridor. 470+/- feet of water frontage, providing expansive views of the Tred Avon River. Gorgeous views. Great location close to downtown Easton and Oxford. The property is approved for a 6-bedroom perc and now features a new path directly to the water. Survey available. Property has some property markers. It appears that part of the neighbors driveway is on the lot.

Enniskillen Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$72,500
Tilghman Island. Clear level building lot with public sewer available. The perfect spot for your new vacation / retirement home. Excellent opportunity to make your island dream come true.

21472 Willey Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166
$8,750,000
6 Beds ⋅ 6 Baths
Wilderness Estate- REVISED OFFERING INCLUDES 5 PARCELS 6.27.25- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 234 acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look and appreciation for the scope of this offering. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that is the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite. The revised offering of The Wilderness, providing 234 acres comprised of 5 recorded parcels with over 3,000 feet of shoreline is a remarkable opportunity to witness life on the Shore.

27295 Southside Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$9,900,000
5 Beds ⋅ 6 Baths
Situated on one of the finest residential parcels in the country, Ship’s Point, is an estate with few rivals anywhere, at any price. The completely private 13+/- acre estate includes a deep water pier, and 270-degree views at the confluence of Trippe’s Creek and the Tred Avon River. The south-west facing manor house has been meticulously renovated by renowned builder Winchester Construction. A visit is necessary to understand the rarity of the views provided by the nearly one-half mile of shoreline that surrounds this home.

6010 Shipyard Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665