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$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

$1,095,000
3 Beds 3 Baths
Waterfront, a deeded boat slip, off-street parking, and a single-car garage with additional storage set the stage for this thoughtfully redesigned coastal retreat in the heart of Oxford. Completely renovated from top to bottom, this 3 bedroom, 2.5 bathroom home blends timeless Eastern Shore charm with luxury finishes and exceptional boating amenities. Every detail has been carefully curated, from the new hardwood flooring and fresh paint throughout to the completely remodeled gourmet kitchen featuring high-end appliances, quartz and soapstone countertops, custom cabinetry, and a butler's pantry connecting the kitchen and dining room. The dining room is anchored by a beautiful masonry fireplace with a gas insert, while the custom "Wine Snug" offers built-in wine racks, a wine refrigerator, and handcrafted wrought iron doors. Designed to maximize its setting, the home captures water views from both the front and rear, with sightlines straight through the home to the water. Upstairs, the primary suite opens to a private balcony overlooking the harbor, and the conveniently located second-floor laundry adds everyday functionality. For boating enthusiasts, the property includes a deeded 40’ boat slip accommodating with approximately 5’ MLW. Ideally located just moments from downtown Oxford, you'll enjoy easy access to marinas, the Oxford Ferry, waterfront parks, and local favorites like Doc's Sunset Grille with frequent live music. Whether you're searching for a full-time residence, weekend getaway, or luxury second home, 100 W. Pier Street offers the perfect blend of water views, boating access, modern updates, and the relaxed Eastern Shore lifestyle.

100 Pier St W, Oxford

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

$1,499,000
3 Beds 3 Baths
Major Price Improvement! Western sunsets and timeless waterfront living define this beautifully restored home on Town Creek in Oxford. A waterside pool, expansive entertaining deck, gazebo and private pier create an exceptional setting for enjoying life on the water. Fabulous gourmet kitchen and inviting family room with a custom built-in bar anchor the home, while warm pine floors add warmth and character throughout. Three bedrooms and three full baths include a spacious waterfront primary suite with a private second-story deck overlooking Town Creek—the perfect place to unwind while taking in spectacular western sunsets. Just moments from Oxford's waterfront park, marina, restaurants and the Oxford-Bellevue Ferry, this distinctive property is privately sited outside the Historic District and features a private pier with approximately 4 + feet of mean low water, providing easy access for boating, kayaking and paddleboarding. Sold As Is

104 Myrtle St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$2,395,000
7 Beds 6 Baths
"Tranquil Waters" is a rare Chesapeake Bay waterfront retreat on Tilghman Island, comprehensively renovated to the highest standard and designed to capture panoramic water views from nearly every room. This extraordinary residence blends refined coastal architecture with the relaxed elegance of Eastern Shore living. Dramatic walls of glass, soaring ceilings, and open living spaces flood the home with natural light while framing endless Bay views, spectacular sunrises, and unforgettable sunsets. The fully renovated interior includes a redesigned chef's kitchen, spa-inspired baths, new windows and sliding doors, updated trim and fireplace features, and extensive system upgrades throughout. Exceptional waterfront amenities include expansive Trex decking, deep-water dockage, a heated indoor pool and spa pavilion, and seamless indoor-outdoor living designed for entertaining and year-round enjoyment. Major capital improvements include new HVAC systems, roof replacement, hot water heater, air purification system, decking, windows, doors, and more, offering true turnkey peace of mind. Beyond its appeal as a private waterfront retreat, "Tranquil Waters" has enjoyed a Successfull Luxury Vacation Rental history, creating an appealing opportunity for buyers seeking both lifestyle and INVESTMENT POTENTIAL. Equally suited as a luxury primary residence, waterfront getaway, or private retreat, "Tranquil Waters" delivers the ultimate Eastern Shore lifestyle: water, light, privacy, and complete escape.

21642 Chicken Point Rd, Tilghman

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

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

24390 Deep Neck Farm Ln, Royal Oak

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

$3,995,000
5 Beds 4 Baths
Experience refined waterfront living in this stunning Lowcountry-style estate, gracefully set on an exceptional waterfront lot among mature Loblolly pines with a coveted southern exposure. Offering sweeping, unobstructed water views, and a rare sense of privacy, the property is bathed in natural light throughout the day, with breathtaking sunrises and and warm, golden reflections in the evening. This 3,800 square foot main residence is complimented by a beautifully appointed 1,200 sq. foot guest cottage, creating an ideal balance of elegance and hospitality. The guest cottage serves as a private retreat, complete with a comfortable living room, galley kitchen, three bedrooms, and a screened porch for quiet relaxation. Inside, timeless craftsmanship defines every space, from reclaimed oak flooring to granite countertops and a meticulously maintained cedar exterior. Outdoors, the lifestyle continues with resort style amenities, including a sparkling in-ground pool, hot tub, firepit and a private 120 foot pier with approximately 7 feet of depth at mean low water- offering effortless access for boating fishing, and enjoying the very best of waterfront living. A rare offering where exceptional land, elegant design, and an unparalleled coastal lifestyle come together.

4335 World Farm Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$2,195,000
4 Beds 4 Baths
LOCATION, CHARM, and beautifully RENOVATED!!!Set on 2.32 glorious acres overlooking Dixon Creek, this beautifully and lovingly maintained 1915 residence offers timeless character, refined comfort, and exceptional waterfront living. Original hardwood floors run throughout much of the home, while expansive windows bathe the traditional floor plan in natural light and frame expansive water views from nearly every room. The main level features gracious formal living and dining rooms, a gourmet kitchen with a beautiful center island and top-tier stainless appliances, and a welcoming family room with wood-burning fireplace. Custom built-ins are thoughtfully integrated throughout the home, reflecting quality craftsmanship and attention to detail. Upstairs, the waterside primary suite offers a fireplace, dual walk-in closets and a luxurious ensuite bath with soaking tub and glass-enclosed shower. Two additional guest bedrooms include one with an ensuite bath and another with access to the hall bath. The third level provides a small loft style BR /flexible bonus room, ideal for an office or studio. Outdoor living is equally inviting, with a waterside screened porch, a poolside screened porch with wet bar, and an additional open deck off the dining room—perfect for enjoying the tranquil setting. The beautifully landscaped grounds feature mature trees, lush plantings, and extensive hardscaping, anchored by a gunite pool with expansive deck and surrounding gardens. Additional structures include a charming former icehouse (currently used as a storage shed) and a larger outbuilding once used as tenant quarters. An attached 2-car garage and a full encapsulated basement offer excellent functionality and versatility. With 280 feet of natural shoreline, a private pier with two slips, boat lift, and 3.5–4' MLW, this property captures the essence of Eastern Shore waterfront living. *Roof- 2011, new siding, new boiler, renovated kitchen and primary bath, encapsulated basement, redecked pier, plus more1!-Septic replaced in 2020 and is for 4 bedrooms-owners have plans for proposed first floor primary suite where existing south side porch currently is.

8075 Leehaven Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$6,890,000
4 Beds 5 Baths
An Exceptional Eastern Shore Estate - 145 Acres of Waterfront, Farmland & Timeless Beauty. There are properties that offer a beautiful setting and then there are properties that possess an unmistakable sense of place. This extraordinary 145 acre estate in coveted Royal Oak is one of the latter - a private waterfront sanctuary where expansive farmland and pasture, mature trees, tranquil ponds and sweeping waterviews converge to create a setting of rare distinction. From the gated drive, the experience is extraordinary. A gracefully paved approach winds through a pastoral landscape of open vistas, three ponds, white-fenced fields and paddocks, and a magnificent canopy of mature sawtooth oaks. Beyond the landscape, the elegant Colonial-style main residence reveals itself, perfectly positioned to capture the serenity of Fox Hole Creek and its long view toward the Tred Avon River. The architecture is gracious and beautifully proportioned. The two-and-a-half-story central section is framed by side wings that step down elegantly to one-story elevations, creating a classic country estate character. Inside, generous proportions, heart pine floors, and natural light complement the home's timeless design. A compelling feature of the residence is its relationship to the water. On the main level, the sunroom, breakfast room, living room, family room, and primary suite all enjoy direct visual connections to the waterfront and open to a sweeping brick terrace extending the length of the house. It is an extraordinary setting for entertaining or simply enjoying the seasons of the Eastern Shore. The second-floor stair hall opens onto a substantial private deck, creating an elevated vantage point overlooking the water and surrounding acreage. Two-bedroom suites and two offices occupy this level, while an additional bedroom suite on the third floor provides comfortable accommodations for guests. The grounds unfold as a collection of distinct destinations. A two-bedroom guest house offers privacy for visitors while the detached garage with apartment above provides versatile space. The resort-style pool is complemented by an elegant pool house featuring a sauna, bath, kitchenette, porch, and lounging areas. A private pier and small boathouse extend the experience to the water, while a greenhouse with its own sitting area offers a tranquil retreat for gardening or quiet reflection. The estate includes a handsome five-stall barn with tack room, washroom, and fenced paddocks. A second barn has been transformed into an impressive garage accommodating classic automobiles—an exceptional amenity that could serve a collector or those seeking extraordinary workspace. Outdoor living is woven throughout the property. The front porch welcomes guests; the expansive covered brick terrace provides an exceptional setting for waterfront entertaining; and a covered brick walkway connects the main residence to the pool and pool house. At the pool, a pergola-shaded lounging area creates an intimate outdoor room designed for long afternoons and summer evenings. The estate is impeccably maintained and equipped for modern living, including a new composite roof, geothermal HVAC, wine cellar, sprinkler system, and high-speed connectivity. Starlink internet is in place, broadband cable is available, and Easton Velocity service is available for hookup. A gated main entrance and separate farm entrance provide convenience and privacy. The Bellevue Ferry to Oxford is nearby, while Easton and St. Michaels are approximately equidistant. Annapolis is approximately 50 miles, Washington, D.C. approximately 70 miles, and Easton Airport: 12 miles. This is a complete Eastern Shore lifestyle—private, elegant, equestrian, agricultural, and intimately connected to the water. SUBDIVISION POTENTIAL presents an additional opportunity, further enhancing the possibilities of this rare offering.

5289 Ferry Neck Rd, Royal Oak

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283

$425,000
3 Beds 2 Baths
The perfect renovated, water view cottage, dating back to circa 1890. Has been meticulously maintained and thoughtfully expanded over the years. Located in the waterfront Village of Neavitt (+/- 70 homes). Move-in mint condition with numerous recent upgrades. First floor primary bedroom, first floor renovated full bathroom, two additional bedrooms and full bathroom upstairs. Outdoor Living: A large screened porch and deck extend the living space outdoors, providing opportunities to enjoy views of the large backyard and breezes off the water. Detached garage/shed with electric for storage of boats in addition to space for a workshop. Solar panels on roof are owned and convey. They substantially lower electric cost to heat and cool the home. Only about 12 miles from the shops and restaurants of charming St Michaels but without St. Michael's town taxes. The village has its own park and playground as well as a public landing with a launch for canoes and kayaks. While currently on a septic system, public sewer is in the process of servicing the town, adding convenience and potentially increasing property value. Overall, this Eastern Shore retreat offers a blend of historical character, modern updates, and a desirable water view location, making it suitable for both full-time residence or part-time retreat. County sewer soon available. Neavitt yard sale moved to September while other village get-togethers/activities remain as scheduled.

6390 Bozman Neavitt Rd, Neavitt

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

$499,000
4 Beds 4 Baths
Desirable Rio Vista Duplex – Live in One Unit and Rent the Other! Rare opportunity to own a duplex in the sought-after Rio Vista community. Move into one unit and generate rental income from the other to help offset your mortgage payments. Properties like this seldom come on the market. Located in a water-access community, residents may enjoy dock access upon approval of the owner's application and payment of applicable fees. The property features two mirror-image units, each offering: Kitchen with a cozy breakfast area Spacious open-concept living and dining room Two generously sized bedrooms One full bath and one half bath This duplex presents an excellent investment opportunity with a strong rental history. Both units are currently tenant-occupied and rent well. Additional opportunity: The neighboring duplex at 1215 is also available for purchase (MLS #MDTA2012950).UST REDUCED - DONT WAIT TO LOOK AT THIS DESIREABLE RIO VISTA LIVING -MOVE

1211 Washington, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283

$1,685,000
5 Beds 5 Baths
UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL . ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL SYSTEMS, ELECTRICAL, WINDOWS, FLOORS ETC ARE NEW- JUST MOVE IN AND ENJOY. FROM NATURAL OAK FLOORS TO MARBLE BATHROOMS, WHITE SPACIOUS KITCHEN WITH GLEAMING GRANITE AND SOAP STONE COUNTERTOPS. EXTENSIVE OUTDOOR LIGHTENING , SPEAKERS, LIGHTENING UNDER THE EVES TURN THIS INTO A MAGICAL PLACE IN THE EVENING. GATHER BY THE HUGE FIREPIT AND ENJOY OUTDOOR LIVING , COOKING AND DINING ON THE VARIOUS PATIOS OR WRAP AROUND DECK. MAINTENANCE EASY MATERIALS HAVE BEEN USED FOR THE DECKING, SIDING AND ROOFING, ATTENTION WAS PAID TO GUTTER SYSTEMS AND GRADING. THE DRIVEWAY IS FRAMED BY BELGIAN COBBLESTONE, STONE COLUMNS GREET YOU WHEN YOU ENTER THE PROPERTY. THIS IS A RARE OPPORTUNITY FOR A TURN KEY PROPERTY IN ST MICHAELS WITHOUT THE TOWN PROPERTY TAXES AND RESTRICTIONS.

9180 Saint Michaels, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283

$2,500,000
5 Beds 1 Baths
Discover one of Talbot County’s rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72-acre agricultural property features approximately 80± acres of tillable ground and is well suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature hardwoods and softwoods, including pine and oak, providing privacy, scenic beauty, and excellent wildlife habitat. The property is zoned agricultural, offering flexibility for farming, recreation, or investment use. Property is being offered in cooperation with Casey Kennedy and Whitetail Properties. The tillable acreage carries an overall NCCPI rating of approximately 57.3, indicating solid, productive ground suitable for row crops, small grains, and conservation programs. The farm boasts over 2,500 feet of water frontage on Miles Creek, offering excellent duck and goose hunting opportunities. The property is located on a known migratory flyway for ducks and geese along the Chesapeake Bay, making it a proven waterfowl destination. A network of trails through the wooded areas leads to a cleared waterfront area on Miles Creek featuring a dock and picnic table, ideal for family activities, swimming, and fishing. A small point along the creek includes a strategically placed booby blind, positioned for effective duck and goose hunting. Additional amenities include multiple duck blinds on Miles Creek and a goose pit. The historic two-story farmhouse, dating to the early 1900s, offers five bedrooms and one full bathroom and features a new roof and siding. Beginning with the main floor, the home offers a large living room, dining room, kitchen, and the first of five bedrooms. The second floor includes four large bedrooms and a full bath. The residence is accessed by a private driveway off Saulsbury Road, providing convenient access while maintaining a high level of privacy. A small shed next to the home provides additional storage. This property is income-producing, with revenue potential from farming operations, CRP enrollment, and hunting leases, making it a versatile investment opportunity, productive farm, or private recreational retreat with waterfront access.

4108 Saulsbury Rd, Trappe

Listing courtesy of VYBE Realty. Contact: 4102204648

$995,000
3 Beds 3 Baths
New price! Amazing opportunity to be on the water in Talbot County. Waterfront home situated on Back Creek in Sherwood. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed lighting. The kitchen is equipped with stainless steel appliances, a built-in pantry, and granite countertops. The open floor plan incorporates a gas fireplace and a formal dining room. The primary suite has a walk-in shower, soaking tub, and walk-in closet. An attached three-car garage provides additional space with an upstairs bonus game/theatre room. The backyard is built for fun with a swimming pool, an outdoor kitchen with bar area, gas fire features, a hot tub, and a pool house for storage. The property also includes a 30x30 pole building with concrete floors, as well as a dock. New septic installed in 2025!

6670 Tilghman Island Rd, Sherwood

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