Trinityvirginia.com Search Results

$10,000,000

Currently one of the largest Farm/Residential Estates available in the State of Maryland and a once in a lifetime opportunity to own it. This 662+ acres waterfront property with 1.8 miles of shoreline known as "Middleville" circa 1880 is truly a magnificent landholding. Located in Talbot County the property is improved with 5 Residents. A newly renovated Main Home that boasts Tidewater Colonial mature coastal charm and expansive views of the water, 3 Guests homes, a Caretakers home and numerous storage and outbuildings. The Land itself consists of 5 parcels making up 390+/- acres of fertile cropland, 175+/- acres of mature forest, 7+ acre waterfowl holding/stocked fishpond, and 6 well fed water-controlled waterfowl impoundments. The property is improved with a pier that has two boats lifts with additional mooring and over 1200' of shoreline revetment. Enormous effort has been directed toward wildlife habitat improvement with an emphasis on waterfowl and quality game. This 'turn -key’ farm on Maryland’s Eastern Shore is a rare find and opportunity, as land is timeless and the chance to own it is not.

4 Beds ⋅ 3 Baths

Currently one of the largest Farm/Residential Estates available in the State of Maryland and a once in a lifetime opportunity to own it. This 662+ acres waterfront property with 1.8 miles of shoreline known as "Middleville" circa 1880 is truly a magnificent landholding. Located in Talbot County the property is improved with 5 Residents. A newly renovated Main Home that boasts Tidewater Colonial mature coastal charm and expansive views of the water, 3 Guests homes, a Caretakers home and numerous storage and outbuildings. The Land itself consists of 5 parcels making up 390+/- acres of fertile cropland, 175+/- acres of mature forest, 7+ acre waterfowl holding/stocked fishpond, and 6 well fed water-controlled waterfowl impoundments. The property is improved with a pier that has two boats lifts with additional mooring and over 1200' of shoreline revetment. Enormous effort has been directed toward wildlife habitat improvement with an emphasis on waterfowl and quality game. This 'turn -key’ farm on Maryland’s Eastern Shore is a rare find and opportunity, as land is timeless and the chance to own it is not.

29031 Howell Point Road, Trappe

Listing courtesy of Holiday Real Estate. Contact:

Selling Office: .

$6,000,000

Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen with vaulted ceiling and excellent light, stainless steel commercial grade appliances, granite countertops. Beautiful draperies throughout the house, and gilded valances in LR. Old wing can serve as caretaker's quarters or home office/conference area or additional BR space. 17 x 16 second story deck off old wing, with outside staircase as well as interior access. Poolside screened porch 17 x 17 with adjacent brick terrace 12 x 26. Front brick floored open porch 12 x 48 with open porch of same size above. Elevator accesses all three stories and is designed for a wheelchair use. Primary bedroom suite has walk-in closets, two large bathrooms, and dressing room with fireplace. Bar off FR has built-ins, two wine refrigerators and an ice machine. Pool 22 x 44 plus apron and brick wall. Pool is long enough for lap swimming. Loop-lock cover is almost new. HIGH SPEED FIBEROPTIC INTERNET SERVICE is available from Easton Velocity. The line has just been run. Owner has not yet connected. Close to the amenities of St. Michaels, with shopping, restaurants and Chesapeake Bay Maritime Museum. Talbot County has an airport on the northwest edge of Easton. 2700 sq ft caretaker's/guest house remodeled 2004/2005. 9.5 ft ceilings; 15 x 6 foyer; 17x 12 eat-in K; 23' x 19' LR with f/p and built in bookcases; 16 ft sq screened porch with great water view;; half bath.; first floor BR 19 x 13 with f/p and en-suite bath; 2d story has 17x 13 BR with fireplace and en-suite bath, 15 x 13 sitting room, 15 x 14 BR. full bath. "B.A.T" (best available technology) septic system new in 2025. Guest house roof less than two years old. Flower cutting beds, vegetable garden and orchard. Art studio (16 ft square) on high ground close to Tilghman Creek. Extensive barns and sheds, including a barn with 5 stalls, tack room and hayloft. Horse caretaker's apartment near barns. Incredible camellias, flowering trees, Spring bulbs. Rich Neck Manor is Talbot County's earliest land grant (1649/1651), The main block of the house was built for Samuel Harrison ca. 1824, Original pine floors, late Federal paneled doors and surrounds, elegant three-story staircase, mantelpieces, etc. The brick dairy (12 x 22) is an architectural "folly" built by Harrison, now used as a chapel. Attached to the Harrison house is a ca. 1740 gambrel-roofed brick kitchen (16 x 36) dating to the days of Matthew Tilghman Ward, while the brick smokehouse (20 x 20), and caretaker/guest house date to ca 1790. Rich Neck Manor was also the home of Revolutionary War patriot Matthew Tilghman. See attachments for history. This property is protected by a land conservation easement and by a MHT historical easement (see documents attached to this listing). The easement holders are helpful with advice and share their knowledge and experience. Hunting is outstanding on this property and the hunting rights are available to buyer. Fishing is unsurpassed, and the Miles River crabs are said to be the largest, heaviest crabs on the Shore. WATER DEPTH: the deepwater harbor is on Tilghman Creek. The "dock" is next to the art studio and consists of a bulkheaded and backfilled area with pilings and slips. It is believed that this area was dredged, but the current depth is uncertain. There is an electronic boat lift here. It has been suggested that the new owner should construct a pier perpendicular to the shore, thereby securing very deep water. The mooring belongs to this property Available partly furnished.

8 Beds ⋅ 5 Baths

Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen with vaulted ceiling and excellent light, stainless steel commercial grade appliances, granite countertops. Beautiful draperies throughout the house, and gilded valances in LR. Old wing can serve as caretaker's quarters or home office/conference area or additional BR space. 17 x 16 second story deck off old wing, with outside staircase as well as interior access. Poolside screened porch 17 x 17 with adjacent brick terrace 12 x 26. Front brick floored open porch 12 x 48 with open porch of same size above. Elevator accesses all three stories and is designed for a wheelchair use. Primary bedroom suite has walk-in closets, two large bathrooms, and dressing room with fireplace. Bar off FR has built-ins, two wine refrigerators and an ice machine. Pool 22 x 44 plus apron and brick wall. Pool is long enough for lap swimming. Loop-lock cover is almost new. HIGH SPEED FIBEROPTIC INTERNET SERVICE is available from Easton Velocity. The line has just been run. Owner has not yet connected. Close to the amenities of St. Michaels, with shopping, restaurants and Chesapeake Bay Maritime Museum. Talbot County has an airport on the northwest edge of Easton. 2700 sq ft caretaker's/guest house remodeled 2004/2005. 9.5 ft ceilings; 15 x 6 foyer; 17x 12 eat-in K; 23' x 19' LR with f/p and built in bookcases; 16 ft sq screened porch with great water view;; half bath.; first floor BR 19 x 13 with f/p and en-suite bath; 2d story has 17x 13 BR with fireplace and en-suite bath, 15 x 13 sitting room, 15 x 14 BR. full bath. "B.A.T" (best available technology) septic system new in 2025. Guest house roof less than two years old. Flower cutting beds, vegetable garden and orchard. Art studio (16 ft square) on high ground close to Tilghman Creek. Extensive barns and sheds, including a barn with 5 stalls, tack room and hayloft. Horse caretaker's apartment near barns. Incredible camellias, flowering trees, Spring bulbs. Rich Neck Manor is Talbot County's earliest land grant (1649/1651), The main block of the house was built for Samuel Harrison ca. 1824, Original pine floors, late Federal paneled doors and surrounds, elegant three-story staircase, mantelpieces, etc. The brick dairy (12 x 22) is an architectural "folly" built by Harrison, now used as a chapel. Attached to the Harrison house is a ca. 1740 gambrel-roofed brick kitchen (16 x 36) dating to the days of Matthew Tilghman Ward, while the brick smokehouse (20 x 20), and caretaker/guest house date to ca 1790. Rich Neck Manor was also the home of Revolutionary War patriot Matthew Tilghman. See attachments for history. This property is protected by a land conservation easement and by a MHT historical easement (see documents attached to this listing). The easement holders are helpful with advice and share their knowledge and experience. Hunting is outstanding on this property and the hunting rights are available to buyer. Fishing is unsurpassed, and the Miles River crabs are said to be the largest, heaviest crabs on the Shore. WATER DEPTH: the deepwater harbor is on Tilghman Creek. The "dock" is next to the art studio and consists of a bulkheaded and backfilled area with pilings and slips. It is believed that this area was dredged, but the current depth is uncertain. There is an electronic boat lift here. It has been suggested that the new owner should construct a pier perpendicular to the shore, thereby securing very deep water. The mooring belongs to this property Available partly furnished.

10770 Rich Neck Road, Claiborne

Listing courtesy of Shoreline Realty. Contact:

Selling Office: .

$3,950,000

Willow Oak Farm is a rare and storied waterfront estate set on 20.0+/- acres along the shores of Harris Creek in Bozman, Maryland. Originally established in 1892, the property offers approximately 983 feet of waterfront and expansive open water views, with exceptional privacy just minutes from St. Michaels and Easton. The 6,000-square-foot French Eclectic main residence, built in 1921, features four en-bedrooms, grand entertaining spaces, and a seamless balance of formal and casual living. A separate cottage provides additional accommodations or workspace. Extensively renovated and modernized by the current owners, the home and infrastructure have been comprehensively upgraded while preserving historic character, creating a turnkey estate designed for both everyday living and refined entertaining.

4 Beds ⋅ 6 Baths

Willow Oak Farm is a rare and storied waterfront estate set on 20.0+/- acres along the shores of Harris Creek in Bozman, Maryland. Originally established in 1892, the property offers approximately 983 feet of waterfront and expansive open water views, with exceptional privacy just minutes from St. Michaels and Easton. The 6,000-square-foot French Eclectic main residence, built in 1921, features four en-bedrooms, grand entertaining spaces, and a seamless balance of formal and casual living. A separate cottage provides additional accommodations or workspace. Extensively renovated and modernized by the current owners, the home and infrastructure have been comprehensively upgraded while preserving historic character, creating a turnkey estate designed for both everyday living and refined entertaining.

7288 Bozman Neavitt Road, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$3,950,000

Tucked within a canopy of trees along Maryland’s Eastern Shore, this remarkable home rests quietly beside the Choptank River. The setting feels worlds away, eighty acres of meadows and woodland that open gently to more than 1,800 feet of private shoreline, where a western exposure captures breathtaking sunsets reflected across the water. The residence at 5084 Ferry Neck Road was shaped by owners whose careers in fine contemporary art inspired a deeply thoughtful approach to design, one that explored geometry, light, and proportion with an almost abstract eye. The resulting octagonal plan draws the landscape into every room, creating a calm rhythm of space and view. A low, horizontal brick façade settles the home into its surroundings, while a lifted roofline and generous overhangs give shelter and balance. Inside, a sweeping staircase curves upward through the central volume, a graceful gesture that anchors the home with quiet strength. In 2024, the property underwent a comprehensive renewal. Porcelain countertops, new glazing, and refined lighting bring a fresh modern sensibility while honoring the original architecture. Approached by a long, tree-lined drive, the home reveals itself gradually, first a glimmer through the woods, then an opening to water and sky. Beyond its immediate beauty, the land itself offers a rare opportunity, with the potential to create a divisible waterfront homesite should the next owner wish to explore it. What remains most striking, however, is its sense of comfort, a home that is inviting, shaped by art, nature, and time.

4 Beds ⋅ 4 Baths

Tucked within a canopy of trees along Maryland’s Eastern Shore, this remarkable home rests quietly beside the Choptank River. The setting feels worlds away, eighty acres of meadows and woodland that open gently to more than 1,800 feet of private shoreline, where a western exposure captures breathtaking sunsets reflected across the water. The residence at 5084 Ferry Neck Road was shaped by owners whose careers in fine contemporary art inspired a deeply thoughtful approach to design, one that explored geometry, light, and proportion with an almost abstract eye. The resulting octagonal plan draws the landscape into every room, creating a calm rhythm of space and view. A low, horizontal brick façade settles the home into its surroundings, while a lifted roofline and generous overhangs give shelter and balance. Inside, a sweeping staircase curves upward through the central volume, a graceful gesture that anchors the home with quiet strength. In 2024, the property underwent a comprehensive renewal. Porcelain countertops, new glazing, and refined lighting bring a fresh modern sensibility while honoring the original architecture. Approached by a long, tree-lined drive, the home reveals itself gradually, first a glimmer through the woods, then an opening to water and sky. Beyond its immediate beauty, the land itself offers a rare opportunity, with the potential to create a divisible waterfront homesite should the next owner wish to explore it. What remains most striking, however, is its sense of comfort, a home that is inviting, shaped by art, nature, and time.

5084 Ferry Neck Road, Royal Oak

Listing courtesy of TTR Sothebys International Realty. Contact:

Selling Office: .

$3,900,000

*A Once-in-a-Lifetime Chesapeake Bay Waterfront Offering – The Iconic Tilghman Island Inn* Welcome to a rare opportunity to own one of the most beautiful, fully reimagined waterfront hospitality properties on Maryland’s Eastern Shore. Set on five acres with sweeping views of the Chesapeake Bay, the Tilghman Island Inn is that extraordinary blend of romance, lifestyle, and investment that rarely becomes available. Established more than 50 years ago, the Inn has been transformed from top to bottom through a meticulous, comprehensive renovation. Today, it lives as a boutique luxury retreat with 20 uniquely designed guest rooms (five with gas fireplaces), a full-service waterfront restaurant and bar, expansive outdoor dining terraces, a sparkling 20' x 40' pool, lush gardens, and expansive private docking with the relaxed charm and quiet sophistication that define the Chesapeake Bay. Guests return year after year for the Inn’s serenity, sunset views, on-site dining, and proximity to St. Michaels, Easton, and Annapolis. For buyers, the value is just as clear: major improvements are already complete, systems are up to date, and recent guest ratings average about 95% across major travel platforms. Whether you envision this as a turnkey boutique hotel, a private family compound, a luxury event destination, or a future waterfront condominium development, the property is positioned for success. The Inn is legally configured as 20 residential condominium units offering flexibility. Property Features: 5-acre waterfront property, 15,000+ sq. ft. hotel and restaurant, 345 ft. vinyl seawall, 20 x 30 ft. T-Dock, 175 ft. floating dock with 7 additional boat slips, 20 uniquely designed guest rooms, 20 x 40 ft. in-ground pool, 30 x 12 ft. fully functional greenhouse, and Lush ornamental and raised bed vegetable gardens For investors seeking a premier turnkey hospitality venture or a high-value waterfront development opportunity, the Tilghman Island Inn presents a rare chance to own an Eastern Shore gem with limitless potential. **NOTE: FOR BROCHURE & VIDEO CONTACT AGENT**

21384 Coopertown Road, Tilghman

Listing courtesy of Compass. Contact:

Selling Office: .

$3,350,000

Perfectly nestled on 4.96± private waterfront acres between Easton and St. Michaels, this extraordinary estate embodies the very best of Eastern Shore living, anchored by rare deep water dockage (6’+ MLW) for the ultimate Chesapeake boating lifestyle. This Royal Oak home’s western exposure offers amazing sunset views across Solitude Creek.This listing also includes a fully prepaid 96-year recorded ground lease on an adjoining 5.48± acre parcel of land -- featuring a picturesque wildflower pasture, a mature 4± acre maple orchard, and charming outbuildings (detached garage and red barn) -- creating unparalleled privacy, beauty, and tranquility. A winding, tree-lined private drive sets the tone for the peaceful retreat that awaits. Inside, panoramic water views fill nearly every room, while the recently updated home blends timeless elegance with warm, inviting comfort. Soaring ceilings, rich hardwood floors, exquisite custom moldings, and expansive living spaces create an atmosphere that is both refined and welcoming. The formal living and dining rooms, each centered around a cozy fireplace, offer inviting spaces for memorable gatherings and celebrations. The light-filled family room features dramatic volume ceilings, oversized windows, a fireplace, and stunning waterfront views that bring the outdoors in. Designed for both everyday living and effortless entertaining, the gourmet kitchen features slate flooring, stainless steel appliances, a walk-in pantry, and a waterside breakfast area where every meal is paired with breathtaking scenery. The luxurious main-level owner’s suite is a private sanctuary with its own fireplace, spectacular water views, dual walk-in closets with custom built-ins, and a spa-inspired bath designed for relaxation. Upstairs, guests and family are comfortably accommodated with a spacious bedroom suite, two additional guest bedrooms, and a versatile bonus room ideal for a home theater, fitness studio, or playroom. Above the oversized, air-conditioned three-car garage, a separate guest retreat with a kitchenette, full bath, and private balcony with beautiful waterfront views offers the perfect space for visiting friends and family. Outdoor living is equally exceptional. A sprawling slate patio, recently added waterside pool, and enclosed porch with vaulted ceilings and flagstone flooring create inviting spaces to relax, entertain, and take in the serene surroundings. Set on a peninsula with more than 1,000 feet of shoreline, the property offers remarkable privacy and endless water views in seemingly every direction. A private deep water pier on Solitude Creek makes boating effortless and permits a memorable arrival by water for your guests. Enoy fishing and crabbing and direct water access to the Choptank River and Chesapeake Bay. Rarely does a property so gracefully combine timeless architecture, resort-style amenities, and one of Talbot County’s most coveted waterfront settings into a place that truly feels like home.

5 Beds ⋅ 6 Baths

Perfectly nestled on 4.96± private waterfront acres between Easton and St. Michaels, this extraordinary estate embodies the very best of Eastern Shore living, anchored by rare deep water dockage (6’+ MLW) for the ultimate Chesapeake boating lifestyle. This Royal Oak home’s western exposure offers amazing sunset views across Solitude Creek.This listing also includes a fully prepaid 96-year recorded ground lease on an adjoining 5.48± acre parcel of land -- featuring a picturesque wildflower pasture, a mature 4± acre maple orchard, and charming outbuildings (detached garage and red barn) -- creating unparalleled privacy, beauty, and tranquility. A winding, tree-lined private drive sets the tone for the peaceful retreat that awaits. Inside, panoramic water views fill nearly every room, while the recently updated home blends timeless elegance with warm, inviting comfort. Soaring ceilings, rich hardwood floors, exquisite custom moldings, and expansive living spaces create an atmosphere that is both refined and welcoming. The formal living and dining rooms, each centered around a cozy fireplace, offer inviting spaces for memorable gatherings and celebrations. The light-filled family room features dramatic volume ceilings, oversized windows, a fireplace, and stunning waterfront views that bring the outdoors in. Designed for both everyday living and effortless entertaining, the gourmet kitchen features slate flooring, stainless steel appliances, a walk-in pantry, and a waterside breakfast area where every meal is paired with breathtaking scenery. The luxurious main-level owner’s suite is a private sanctuary with its own fireplace, spectacular water views, dual walk-in closets with custom built-ins, and a spa-inspired bath designed for relaxation. Upstairs, guests and family are comfortably accommodated with a spacious bedroom suite, two additional guest bedrooms, and a versatile bonus room ideal for a home theater, fitness studio, or playroom. Above the oversized, air-conditioned three-car garage, a separate guest retreat with a kitchenette, full bath, and private balcony with beautiful waterfront views offers the perfect space for visiting friends and family. Outdoor living is equally exceptional. A sprawling slate patio, recently added waterside pool, and enclosed porch with vaulted ceilings and flagstone flooring create inviting spaces to relax, entertain, and take in the serene surroundings. Set on a peninsula with more than 1,000 feet of shoreline, the property offers remarkable privacy and endless water views in seemingly every direction. A private deep water pier on Solitude Creek makes boating effortless and permits a memorable arrival by water for your guests. Enoy fishing and crabbing and direct water access to the Choptank River and Chesapeake Bay. Rarely does a property so gracefully combine timeless architecture, resort-style amenities, and one of Talbot County’s most coveted waterfront settings into a place that truly feels like home.

25610 Chance Farm Court, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$3,200,000

4 Beds ⋅ 6 Baths

703 Riverview Terrace, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: .

$3,200,000

Welcome to Rivermark - a true waterfront retreat in St. Michaels on the Eastern Shore. This custom-built home is an artistic masterpiece with five octagonal interconnected wings, creating distinct yet flowing spaces and breathtaking panoramic views of Porters Creek, Miles River, Wye River and the Eastern Bay from every room. With architecture inspired by the French West Indies, this home has been thoughtfully designed with both entertainment and relaxation in mind. Entering through the foyer, the heart of the home is the Great Room which contains soaring ceilings. This opens to a sun-drenched solarium with travertine flooring and floor-to-ceiling windows that wrap around the interconnected spaces of the sunroom, dining room, and kitchen. Entertaining guests is effortless with the gourmet kitchen that is fully equipped with stainless steel appliances, an Aga stove, granite countertops, a large center island, and custom shelving/cabinetry. With both garden and water views the dual office/study spaces have custom floor-to-ceiling built-ins and wood paneling. The primary suite and a sanctuary unto itself, constructed with 18-foot ceilings and a spa-inspired en-suite bathroom fireplace and private outdoor patio. On the opposite wing of the home, you'll discover two additional bright bedrooms with custom lighting and a spacious shared bathroom. A unique feature of this property is the spa-inspired, glass enclosed swimming pool which overlooks the Miles River. The area is complete with an adjacent sunroom, green house, sauna, and full bath in this zen-like setting. A separate guest house provides privacy with its own entrance, offering two bedrooms, two bathrooms, a kitchen, and a comfortable living space. Outdoors, this property offers a rarely available opportunity of 750 feet of a rip-rapped waterfront, deep waters and a 150-foot private dock with boat lift - offering direct access to the Eastern Shore’s waterways and nearby waterfront dining. The extensive professionally manicured landscaped grounds feature a tranquil koi pond with a fountain, lush gardens, abundant verdant trees, and brick patio with grill area. Rivermark was featured by the Talbot County Garden Club in the Maryland House & Garden Pilgrimage. Don’t miss your chance to view this unique property in person to appreciate the incredible details. Experience the best of St. Michaels living at Rivermark—where luxury, comfort, and natural beauty converge in perfect harmony.

5 Beds ⋅ 6 Baths

Welcome to Rivermark - a true waterfront retreat in St. Michaels on the Eastern Shore. This custom-built home is an artistic masterpiece with five octagonal interconnected wings, creating distinct yet flowing spaces and breathtaking panoramic views of Porters Creek, Miles River, Wye River and the Eastern Bay from every room. With architecture inspired by the French West Indies, this home has been thoughtfully designed with both entertainment and relaxation in mind. Entering through the foyer, the heart of the home is the Great Room which contains soaring ceilings. This opens to a sun-drenched solarium with travertine flooring and floor-to-ceiling windows that wrap around the interconnected spaces of the sunroom, dining room, and kitchen. Entertaining guests is effortless with the gourmet kitchen that is fully equipped with stainless steel appliances, an Aga stove, granite countertops, a large center island, and custom shelving/cabinetry. With both garden and water views the dual office/study spaces have custom floor-to-ceiling built-ins and wood paneling. The primary suite and a sanctuary unto itself, constructed with 18-foot ceilings and a spa-inspired en-suite bathroom fireplace and private outdoor patio. On the opposite wing of the home, you'll discover two additional bright bedrooms with custom lighting and a spacious shared bathroom. A unique feature of this property is the spa-inspired, glass enclosed swimming pool which overlooks the Miles River. The area is complete with an adjacent sunroom, green house, sauna, and full bath in this zen-like setting. A separate guest house provides privacy with its own entrance, offering two bedrooms, two bathrooms, a kitchen, and a comfortable living space. Outdoors, this property offers a rarely available opportunity of 750 feet of a rip-rapped waterfront, deep waters and a 150-foot private dock with boat lift - offering direct access to the Eastern Shore’s waterways and nearby waterfront dining. The extensive professionally manicured landscaped grounds feature a tranquil koi pond with a fountain, lush gardens, abundant verdant trees, and brick patio with grill area. Rivermark was featured by the Talbot County Garden Club in the Maryland House & Garden Pilgrimage. Don’t miss your chance to view this unique property in person to appreciate the incredible details. Experience the best of St. Michaels living at Rivermark—where luxury, comfort, and natural beauty converge in perfect harmony.

9791 Pintail Place, Saint Michaels

Listing courtesy of Compass. Contact:

Selling Office: .

$3,015,000

SERENE VIEWS AWAIT YOU AT YOUR EXCLUSIVE WATERFRONT , GORGEOUS ACRES ON PRIVATE MAJESTIC PENINSULA IN BETWEEN THE COASTAL TOWNS ST MICHAELS , EASTON. JUST A SHORT DRIVE TO ITS SHOPS, RESTAURANTS, CAFES, MUSEUMS AND ALL THE AREA HAS TO OFFER. THIS FABULOUS PROPERTY LETS YOU EXPERIENCE EASTERN SHORE LIFE STYLE AS ITS BEST. OPERATED AS A SUCESSFUL VACATION RENTAL IT HAS GONE THRU VARIOUS RENOVATIONS, LASTLY A MAJOR ONE IN 2020 AND 2021. YOUR CHANCE TO PURCHASE A 6 BEDROOM 6 BATHROOM TURN KEY PROPERTY TO ENJOY WITH YOUR FAMILY AND SHARE AS A RENTAL WITH FAMILIES THAT COME TO VISIT . THE PROEPRTY IS BEING SOLD TURN KEY WITH ALL CONTENTS.

6 Beds ⋅ 7 Baths

SERENE VIEWS AWAIT YOU AT YOUR EXCLUSIVE WATERFRONT , GORGEOUS ACRES ON PRIVATE MAJESTIC PENINSULA IN BETWEEN THE COASTAL TOWNS ST MICHAELS , EASTON. JUST A SHORT DRIVE TO ITS SHOPS, RESTAURANTS, CAFES, MUSEUMS AND ALL THE AREA HAS TO OFFER. THIS FABULOUS PROPERTY LETS YOU EXPERIENCE EASTERN SHORE LIFE STYLE AS ITS BEST. OPERATED AS A SUCESSFUL VACATION RENTAL IT HAS GONE THRU VARIOUS RENOVATIONS, LASTLY A MAJOR ONE IN 2020 AND 2021. YOUR CHANCE TO PURCHASE A 6 BEDROOM 6 BATHROOM TURN KEY PROPERTY TO ENJOY WITH YOUR FAMILY AND SHARE AS A RENTAL WITH FAMILIES THAT COME TO VISIT . THE PROEPRTY IS BEING SOLD TURN KEY WITH ALL CONTENTS.

6448 Partridge Lane, Royal Oak

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

Selling Office: .

$2,975,000

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.

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 Drive, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$2,950,000

8781 Tilghman Island Road presents a rare opportunity to own a custom-designed, Daffin-built Chesapeake Bay estate set on 21±acres between historic St. Michaels and Tilghman Island. Constructed with a timeless brick exterior and encompassing approximately 6,500± square feet, this five-bedroom, five-and-a-half-bath residence was thoughtfully designed to embrace its extraordinary waterfront setting, where expansive Chesapeake Bay views and unforgettable western sunsets become part of everyday life. The home's classic architecture is highlighted by stacked waterfront porches, a spacious front balcony, and walls of windows that capture panoramic views from nearly every principal room. Two gas fireplaces add warmth to the generous living spaces, while abundant storage and a thoughtful floor plan provide comfort and functionality for both everyday living and entertaining. The main level is anchored by a spacious waterfront primary suite featuring a walk-in closet, oversized water closet, an en-suite bath with a tile walk-in shower and a separate tub, and a private enclosed porch overlooking the Bay. Upstairs, three generously sized en-suite bedrooms offer exceptional accommodations. Two bedrooms open to the front balcony, while the waterfront suite enjoys direct access to the upper waterfront porch. The third floor offers an additional en-suite bedroom along with a versatile bonus room ideal as a home office, craft room, playroom, fitness space, or additional storage. Outside, approximately 662± feet of riprapped Chesapeake Bay shoreline frames the property, while mature trees create a beautiful natural setting. Approximately four acres lie outside of the agricultural assessment, with the remaining acreage benefiting from agricultural tax status. Positioned along the Eastern Bay Water Trail, the property offers experienced kayakers direct access to one of the region's premier paddling routes and the opportunity to explore the Chesapeake Bay from your own shoreline. A detached garage offers exceptional flexibility and could serve as a future pool house, workshop, studio, or, where permitted, guest accommodations. The home is equipped with five-zone heat pumps with central air conditioning, along with separate ductless HVAC systems serving both waterfront porches and the detached garage, providing year-round comfort throughout the property. Combining quality craftsmanship, a premier Chesapeake Bay location, and over 21± acres of land, this exceptional waterfront estate offers an increasingly rare opportunity to enjoy privacy, space, and some of the Eastern Shore's most spectacular sunset views.

5 Beds ⋅ 6 Baths

8781 Tilghman Island Road presents a rare opportunity to own a custom-designed, Daffin-built Chesapeake Bay estate set on 21±acres between historic St. Michaels and Tilghman Island. Constructed with a timeless brick exterior and encompassing approximately 6,500± square feet, this five-bedroom, five-and-a-half-bath residence was thoughtfully designed to embrace its extraordinary waterfront setting, where expansive Chesapeake Bay views and unforgettable western sunsets become part of everyday life. The home's classic architecture is highlighted by stacked waterfront porches, a spacious front balcony, and walls of windows that capture panoramic views from nearly every principal room. Two gas fireplaces add warmth to the generous living spaces, while abundant storage and a thoughtful floor plan provide comfort and functionality for both everyday living and entertaining. The main level is anchored by a spacious waterfront primary suite featuring a walk-in closet, oversized water closet, an en-suite bath with a tile walk-in shower and a separate tub, and a private enclosed porch overlooking the Bay. Upstairs, three generously sized en-suite bedrooms offer exceptional accommodations. Two bedrooms open to the front balcony, while the waterfront suite enjoys direct access to the upper waterfront porch. The third floor offers an additional en-suite bedroom along with a versatile bonus room ideal as a home office, craft room, playroom, fitness space, or additional storage. Outside, approximately 662± feet of riprapped Chesapeake Bay shoreline frames the property, while mature trees create a beautiful natural setting. Approximately four acres lie outside of the agricultural assessment, with the remaining acreage benefiting from agricultural tax status. Positioned along the Eastern Bay Water Trail, the property offers experienced kayakers direct access to one of the region's premier paddling routes and the opportunity to explore the Chesapeake Bay from your own shoreline. A detached garage offers exceptional flexibility and could serve as a future pool house, workshop, studio, or, where permitted, guest accommodations. The home is equipped with five-zone heat pumps with central air conditioning, along with separate ductless HVAC systems serving both waterfront porches and the detached garage, providing year-round comfort throughout the property. Combining quality craftsmanship, a premier Chesapeake Bay location, and over 21± acres of land, this exceptional waterfront estate offers an increasingly rare opportunity to enjoy privacy, space, and some of the Eastern Shore's most spectacular sunset views.

8781 Tilghman Island Road, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$2,900,000

"Fox Haven" Privately sited on almost 10 acres with 900+ feet of protected waterfront, this impressive retreat captures breathtaking wide water views from nearly every vantage point. Offering approximately 4,800 square feet of living space across three finished levels, the home is designed for comfort and versatility, with wood flooring, a well-appointed kitchen with island, and distinct living and dining areas. Five bedrooms are complemented by an upper-level office or den and a third-floor craft room with cork flooring. A spacious game room with pool table, three fireplaces, wine room, and extensive storage enhance the interior. Outdoors, enjoy a screened porch, in-ground pool, detached garage, multiple outbuildings, and a private pier equipped with two lifts—an ideal setting for boating enthusiasts and those seeking a peaceful waterfront lifestyle.

5 Beds ⋅ 5 Baths

"Fox Haven" Privately sited on almost 10 acres with 900+ feet of protected waterfront, this impressive retreat captures breathtaking wide water views from nearly every vantage point. Offering approximately 4,800 square feet of living space across three finished levels, the home is designed for comfort and versatility, with wood flooring, a well-appointed kitchen with island, and distinct living and dining areas. Five bedrooms are complemented by an upper-level office or den and a third-floor craft room with cork flooring. A spacious game room with pool table, three fireplaces, wine room, and extensive storage enhance the interior. Outdoors, enjoy a screened porch, in-ground pool, detached garage, multiple outbuildings, and a private pier equipped with two lifts—an ideal setting for boating enthusiasts and those seeking a peaceful waterfront lifestyle.

5995 Elston Shore Road, Neavitt

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$2,850,000

"WHITEHALL FARM" 99 +/- exclusive Talbot County waterfront acres. Property consists of four parcels including three platted SDA's and over 2000 ft of shoreline bordering Irish Creek. MLW water depth average 2-3 ft. Parcels 1 and 3 percs are currently in re-evaluation process with the county. Parcel 2 improvements include a 2784 sq ft 4 bd 3 bath farmhouse and an updated BAT septic along with two 40 x 35 storage barns. 37 +/- tillable ag acres make up the interior of the farm. Timberland acres span 38 +/- acres upon the entryway with a mix of loblolly pine and hardwood. A 2 acre freshwater pond and a 5 acre plant and flood impoundment serve as crucial habitat for wintering waterfowl. This property is well suited for a large family compound in a highly desirable area of Talbot County and offers unlimited amenities. Conveniently located 10 minutes from St. Michaels, 15 minutes from Easton, and a short drive to the Oxford/ Bellevue Ferry, you will find several restaurants, shops, and activities nearby.

4 Beds ⋅ 3 Baths

"WHITEHALL FARM" 99 +/- exclusive Talbot County waterfront acres. Property consists of four parcels including three platted SDA's and over 2000 ft of shoreline bordering Irish Creek. MLW water depth average 2-3 ft. Parcels 1 and 3 percs are currently in re-evaluation process with the county. Parcel 2 improvements include a 2784 sq ft 4 bd 3 bath farmhouse and an updated BAT septic along with two 40 x 35 storage barns. 37 +/- tillable ag acres make up the interior of the farm. Timberland acres span 38 +/- acres upon the entryway with a mix of loblolly pine and hardwood. A 2 acre freshwater pond and a 5 acre plant and flood impoundment serve as crucial habitat for wintering waterfowl. This property is well suited for a large family compound in a highly desirable area of Talbot County and offers unlimited amenities. Conveniently located 10 minutes from St. Michaels, 15 minutes from Easton, and a short drive to the Oxford/ Bellevue Ferry, you will find several restaurants, shops, and activities nearby.

25320 White Hall Road, Royal Oak

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: .

$2,795,000

Perfectly positioned along the prestigious shores of the Tred Avon River, this extraordinary waterfront estate offers breathtaking water views from nearly every room and an unparalleled blend of luxury, craftsmanship, and cutting-edge sustainability. Designed to embrace its spectacular setting, the three-level main residence features exceptional attention to detail throughout, including rich hardwood flooring, custom millwork, hidden built-in cabinetry, and exquisite finishes at every turn. A gracious main hallway draws your eye directly to the covered waterside porch, creating a seamless connection between the home's elegant interior and its stunning riverfront backdrop. The heart of the home is a chef's kitchen appointed with marble countertops, a spacious center island, and thoughtfully designed gathering spaces that flow effortlessly into the dining room and inviting sitting room with a fireplace. The second-floor primary suite serves as a private retreat, featuring access to its own waterfront balcony overlooking the Tred Avon River. The luxurious primary bath offers a beautiful tiled steam shower with water views, a dedicated vanity area, and an expansive custom walk-in closet with integrated laundry. Outside, an incredible overflow pool creates a resort-like setting where endless river views take center stage. Guests will enjoy complete privacy in the detached guest house, which includes a kitchenette and full bath. A detached one-car garage provides additional storage and convenience. Built with both comfort and efficiency in mind, the property showcases Tesla Solar Roof shingles on both the main residence and guest house, geothermal heating and cooling, radiant floor heating throughout the first and second levels, seven Tesla backup batteries providing power during outages, and elevator access serving the first and second floors. A rare offering in the heart of historic Oxford, 200 West Street represents waterfront living at its finest—where timeless elegance, modern innovation, and spectacular views come together in one unforgettable property. --- {Luxury & Special Features} Waterfront primary suite featuring a private balcony, rain shower, and steam bath | Chef's kitchen with two freezer drawers and built-in plate warmer | Continuous warm water circulation system throughout the home | Dedicated water pressure enhancement system | Elevator serving the first and second floors | Radiant floor heating throughout the first and second levels | Geothermal heating and cooling system | Tesla Solar Roof shingles on the main residence and guest house | Seven Tesla Powerwall backup batteries providing power during outages | Tesla electric vehicle charging station | Resort-style overflow pool overlooking the Tred Avon River | Electric retractable awnings | Detached guest house with kitchenette and full bath | Detached one-car garage

4 Beds ⋅ 4 Baths

Perfectly positioned along the prestigious shores of the Tred Avon River, this extraordinary waterfront estate offers breathtaking water views from nearly every room and an unparalleled blend of luxury, craftsmanship, and cutting-edge sustainability. Designed to embrace its spectacular setting, the three-level main residence features exceptional attention to detail throughout, including rich hardwood flooring, custom millwork, hidden built-in cabinetry, and exquisite finishes at every turn. A gracious main hallway draws your eye directly to the covered waterside porch, creating a seamless connection between the home's elegant interior and its stunning riverfront backdrop. The heart of the home is a chef's kitchen appointed with marble countertops, a spacious center island, and thoughtfully designed gathering spaces that flow effortlessly into the dining room and inviting sitting room with a fireplace. The second-floor primary suite serves as a private retreat, featuring access to its own waterfront balcony overlooking the Tred Avon River. The luxurious primary bath offers a beautiful tiled steam shower with water views, a dedicated vanity area, and an expansive custom walk-in closet with integrated laundry. Outside, an incredible overflow pool creates a resort-like setting where endless river views take center stage. Guests will enjoy complete privacy in the detached guest house, which includes a kitchenette and full bath. A detached one-car garage provides additional storage and convenience. Built with both comfort and efficiency in mind, the property showcases Tesla Solar Roof shingles on both the main residence and guest house, geothermal heating and cooling, radiant floor heating throughout the first and second levels, seven Tesla backup batteries providing power during outages, and elevator access serving the first and second floors. A rare offering in the heart of historic Oxford, 200 West Street represents waterfront living at its finest—where timeless elegance, modern innovation, and spectacular views come together in one unforgettable property. --- {Luxury & Special Features} Waterfront primary suite featuring a private balcony, rain shower, and steam bath | Chef's kitchen with two freezer drawers and built-in plate warmer | Continuous warm water circulation system throughout the home | Dedicated water pressure enhancement system | Elevator serving the first and second floors | Radiant floor heating throughout the first and second levels | Geothermal heating and cooling system | Tesla Solar Roof shingles on the main residence and guest house | Seven Tesla Powerwall backup batteries providing power during outages | Tesla electric vehicle charging station | Resort-style overflow pool overlooking the Tred Avon River | Electric retractable awnings | Detached guest house with kitchenette and full bath | Detached one-car garage

200 West Street, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$2,750,000

Set on a private point overlooking Boone Creek and the Choptank River in Oxford, this exceptional 4BR/2.5BA modern farmhouse offers panoramic water views and refined coastal living on 2.4 acres. Built in 2018, the home showcases high-end finishes, hardwood flooring throughout, and a light-filled, open design with walls of windows capturing the surrounding waterfront. A welcoming, expansive front porch introduces the main level, where the cathedral-ceiling living room with gas fireplace flows seamlessly into a gourmet kitchen with top-tier appliances—ideal for both everyday living and entertaining. The main-level primary suite enjoys water views and privacy, while the second level overlooks the living space below and features three additional bedrooms and a full hall bath. Outdoor amenities complete the offering, including a waterside deck, new gunite pool (Aqua Pool), private pier with two slips and floating dock, riprapped shoreline, detached two-car garage (transformed and finished into a large office), and beautifully landscaped grounds—perfectly capturing the relaxed elegance and timeless appeal of Eastern Shore living.

4 Beds ⋅ 3 Baths

Set on a private point overlooking Boone Creek and the Choptank River in Oxford, this exceptional 4BR/2.5BA modern farmhouse offers panoramic water views and refined coastal living on 2.4 acres. Built in 2018, the home showcases high-end finishes, hardwood flooring throughout, and a light-filled, open design with walls of windows capturing the surrounding waterfront. A welcoming, expansive front porch introduces the main level, where the cathedral-ceiling living room with gas fireplace flows seamlessly into a gourmet kitchen with top-tier appliances—ideal for both everyday living and entertaining. The main-level primary suite enjoys water views and privacy, while the second level overlooks the living space below and features three additional bedrooms and a full hall bath. Outdoor amenities complete the offering, including a waterside deck, new gunite pool (Aqua Pool), private pier with two slips and floating dock, riprapped shoreline, detached two-car garage (transformed and finished into a large office), and beautifully landscaped grounds—perfectly capturing the relaxed elegance and timeless appeal of Eastern Shore living.

4361 Bachelors Point Road, Oxford

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

Selling Office: .

$2,730,000

Travel along an enchanting and winding drive, through a park-like setting, across the bridge, to the grand reveal of a prairie-style home boasting coastal-meets-contemporary design elements, all situated in the desirable Bantry community of Easton! On a private cove feeding into the Miles River, this property offers expansive, breathtaking water views and, the opportunity for boating, kayaking and enjoying the flight of many types of waterfowl (and an occasional eagle!). The property has been completely reimagined by the current owners over the last three years--fully renovated kitchen with stainless appliances, quartzite leathered waterfall island; beautiful pantry; updated owners' suite inclusive of a water-view primary bedroom, sitting room, double- vanity primary bath and walk-in closet (all on the main floor); another large bedroom and flex space/exercise room on the main floor share a full bath; laundry room; and two more bedrooms upstairs (both with water views) which share another full bath. You can't miss the magnificent view from the vaulted-ceiling great room which overlooks the cove on one side and offers a grand brick fireplace for those chilly winter eves on the opposite end. The home also provides a formal dining room, office with built-ins, sitting room with garden-view, large mud room with custom wallpaper, a wood burning stove, and a fun bar/entertaining area with custom elements; half-bath; and an enclosed cedar-lined porch overlooking the water. New interior doors and flooring throughout. Updated landscaping, flagstone patios, deck with cable rails, and rock gardens are designed to be low-maintenance. The deep bronze Anderson doors and many of the windows are new, as is the deep blue siding on the home, a 60 ft pier w/200 sq ft platform dock with 8000 lb boat lift (dock/lift installed by Weems in 2023). Anderson windows on the water side of the property come with Tru-Scene invisible screens. Two 5-ton HVAC units and new duct work installed in the last three years. Beautiful new roof and skylights installed in 2025. The home is at 8' elevation and not in a federal flood zone. The water depth at the dock is 2-2.5' MLW. Living shoreline with native grasses and flowers. The 21' center console Sea Hunt boat with a 200 HP Yamaha motor with approximately 100 hours is kept on the dock lift and conveys with an acceptable offer. The property has numerous large closets for storage, but also a three-car garage at the main house. A detached three bay garage/workshop with electric, insulation, water and heat, is perfect for a car or boat enthusiast. The sides bays are two cars deep and the large center bay (functioning as a workshop) that is 35'x35' can store a boat or up to 4 cars. Easton MD is considered the New Hamptons per Forbes magazine; a culinary mecca and cultural destination featuring museums, shops, theater, art festivals and more! This property will be a short drive to the new regional hospital anticipated for 2028 and is approximately 1.5 hours to Baltimore and Washington D.C..

4 Beds ⋅ 4 Baths

Travel along an enchanting and winding drive, through a park-like setting, across the bridge, to the grand reveal of a prairie-style home boasting coastal-meets-contemporary design elements, all situated in the desirable Bantry community of Easton! On a private cove feeding into the Miles River, this property offers expansive, breathtaking water views and, the opportunity for boating, kayaking and enjoying the flight of many types of waterfowl (and an occasional eagle!). The property has been completely reimagined by the current owners over the last three years--fully renovated kitchen with stainless appliances, quartzite leathered waterfall island; beautiful pantry; updated owners' suite inclusive of a water-view primary bedroom, sitting room, double- vanity primary bath and walk-in closet (all on the main floor); another large bedroom and flex space/exercise room on the main floor share a full bath; laundry room; and two more bedrooms upstairs (both with water views) which share another full bath. You can't miss the magnificent view from the vaulted-ceiling great room which overlooks the cove on one side and offers a grand brick fireplace for those chilly winter eves on the opposite end. The home also provides a formal dining room, office with built-ins, sitting room with garden-view, large mud room with custom wallpaper, a wood burning stove, and a fun bar/entertaining area with custom elements; half-bath; and an enclosed cedar-lined porch overlooking the water. New interior doors and flooring throughout. Updated landscaping, flagstone patios, deck with cable rails, and rock gardens are designed to be low-maintenance. The deep bronze Anderson doors and many of the windows are new, as is the deep blue siding on the home, a 60 ft pier w/200 sq ft platform dock with 8000 lb boat lift (dock/lift installed by Weems in 2023). Anderson windows on the water side of the property come with Tru-Scene invisible screens. Two 5-ton HVAC units and new duct work installed in the last three years. Beautiful new roof and skylights installed in 2025. The home is at 8' elevation and not in a federal flood zone. The water depth at the dock is 2-2.5' MLW. Living shoreline with native grasses and flowers. The 21' center console Sea Hunt boat with a 200 HP Yamaha motor with approximately 100 hours is kept on the dock lift and conveys with an acceptable offer. The property has numerous large closets for storage, but also a three-car garage at the main house. A detached three bay garage/workshop with electric, insulation, water and heat, is perfect for a car or boat enthusiast. The sides bays are two cars deep and the large center bay (functioning as a workshop) that is 35'x35' can store a boat or up to 4 cars. Easton MD is considered the New Hamptons per Forbes magazine; a culinary mecca and cultural destination featuring museums, shops, theater, art festivals and more! This property will be a short drive to the new regional hospital anticipated for 2028 and is approximately 1.5 hours to Baltimore and Washington D.C..

9716 Bantry Road, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: .

$2,695,000

Set in the highly sought-after Patrick’s Plains community, 28211 Brick Row Drive is an exceptionally maintained and thoughtfully appointed waterfront residence overlooking the serene waters of Island Creek. Bathed in natural light, the home welcomes you with a stunning foyer and living room featuring floor-to-ceiling windows, skylights, and a gas fireplace, seamlessly connecting to the expansive deck. Designed for both everyday living and elegant entertaining, the home offers a formal dining area and beautiful hardwood flooring throughout. The gourmet kitchen is a true centerpiece, boasting a massive island, Viking gas range, Sub-Zero refrigerator, stainless steel appliances, and abundant pantry storage. Just off the kitchen, the family room impresses with cathedral ceilings, a gas fireplace, sweeping water views, and direct access to a screened-in porch. The main-level primary suite is a private retreat, complete with a spacious walk-in closet and direct access to the back deck, where you can enjoy tranquil poolside and waterfront views. The luxurious primary bath features a cathedral ceiling, a standalone soaking tub, and a glass-enclosed shower. The lower level offers incredible flexibility as a poolside retreat or in-law suite, with its own living room, recreation space, bedroom, full bath, and kitchenette. Completing the home is a rare three-car garage, adding both convenience and functionality. The owner has completed many upgrades, including a new pool, pier improvements, three new HVAC systems, a new driveway, and a water treatment system, along with many other enhancements (full list available). With its prime waterfront setting, abundant natural light, and exceptional living spaces, this home offers a truly elevated lifestyle in one of the area’s most desirable communities.

5 Beds ⋅ 6 Baths

Set in the highly sought-after Patrick’s Plains community, 28211 Brick Row Drive is an exceptionally maintained and thoughtfully appointed waterfront residence overlooking the serene waters of Island Creek. Bathed in natural light, the home welcomes you with a stunning foyer and living room featuring floor-to-ceiling windows, skylights, and a gas fireplace, seamlessly connecting to the expansive deck. Designed for both everyday living and elegant entertaining, the home offers a formal dining area and beautiful hardwood flooring throughout. The gourmet kitchen is a true centerpiece, boasting a massive island, Viking gas range, Sub-Zero refrigerator, stainless steel appliances, and abundant pantry storage. Just off the kitchen, the family room impresses with cathedral ceilings, a gas fireplace, sweeping water views, and direct access to a screened-in porch. The main-level primary suite is a private retreat, complete with a spacious walk-in closet and direct access to the back deck, where you can enjoy tranquil poolside and waterfront views. The luxurious primary bath features a cathedral ceiling, a standalone soaking tub, and a glass-enclosed shower. The lower level offers incredible flexibility as a poolside retreat or in-law suite, with its own living room, recreation space, bedroom, full bath, and kitchenette. Completing the home is a rare three-car garage, adding both convenience and functionality. The owner has completed many upgrades, including a new pool, pier improvements, three new HVAC systems, a new driveway, and a water treatment system, along with many other enhancements (full list available). With its prime waterfront setting, abundant natural light, and exceptional living spaces, this home offers a truly elevated lifestyle in one of the area’s most desirable communities.

28211 Brick Row Drive, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$2,687,753

219.435+- Acres Of Prime Eastern Shore Hunting Land With Tillable Fields, T Located in sought-after Talbot County near Trappe, Maryland, this 219.435 acre property presents a rare opportunity to own a diverse and highly productive piece of Eastern Shore land. With approximately 150 acres of tillable ground and former CRP acreage, this farm offers both income potential and exceptional wildlife habitat. The balance of the property consists of mature timber, creating ideal cover, bedding areas, and natural travel corridors for wildlife. This property is a proven hunting tract that supports strong populations of whitetail deer, with the area well known for producing mature bucks. The combination of agricultural fields, timber edges, and secluded pockets provides excellent stand locations and consistent deer movement. Wild turkeys are frequently observed throughout the property, taking advantage of the open fields and wooded sections for feeding and roosting. Water features further enhance the recreational value of this tract. A pond located on the property attracts Canada geese during the winter months and provides additional opportunities for puddle duck hunting. The property also features frontage along Raccoon Creek, expanding waterfowl hunting potential with opportunities to target species such as mallards, wood ducks, and black ducks. This combination of field, timber, and water creates a well-rounded hunting environment that is increasingly difficult to find in one tract. Access to the property is convenient with road frontage on both Kates Point Road and Bambury Road, allowing for flexible entry points and ease of equipment movement. Despite this accessibility, the property offers a high level of privacy, with its size and layout providing seclusion for both recreational use and future improvements. One of the standout features of this property is a small, secluded field located toward the rear of the tract. This area offers excellent potential for a dedicated food plot, additional farming, or re-enrollment into conservation programs. Its location provides an ideal setting for attracting and holding wildlife away from pressure. Importantly, the property is not encumbered by a conservation easement, giving the next owner flexibility in how the land is utilized. Whether the goal is to continue farming operations, enhance wildlife habitat, or establish a private recreational retreat, this tract offers a wide range of possibilities. Large, contiguous parcels with this blend of tillable acreage, timber, water frontage, and strong wildlife presence are increasingly rare on Marylands Eastern Shore. This Talbot County property stands out as a premier opportunity for hunters, investors, and outdoor enthusiasts looking to secure a versatile and productive piece of land.

00 Kates Point Road, Trappe

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: .

$2,680,000

Just 5-miles outside historic St. Michaels, MD...Classic "Eastern Shore Waterfront Retreat," featuring a substantial 5,400+ sq. ft. home, thoughtfully designed to capture cooling SW summer breezes and spectacular sunset views across the sparkling waters of Harris Creek. Sited on 8.26 private acres w/over 300' of natural "living Shoreline," features of the brick home include high ceilings (including a cathedral ceiling in the family room and tray ceiling in the primary bedroom); four (or 5) bedrooms; 4 full and 2 half baths; large primary suite w/recently updated bath; gourmet kitchen w/island and breakfast room connected to a wonderful family room w/fireplace. Generous waterside glass to maximize the water views from most rooms. Beautiful waterside swimming pool (heated), surrounded by a spacious multi-level patio. For Chesapeake bay boating, there is a substantial 6' wide x 200' dock w/electric boat lift. Water depth at the dock on a typical low tide (MLW) is over 5 ft. This is a great boating, fishing and crabbing location. Tilghman Island's waterside restaurants, marinas and the open waters of Chesapeake Bay are just a short, scenic boat ride downstream from the dock. By car, the Town of St. Michaels with its many fine restaurants and attractions is less than 10-minutes away (5-miles). The house is well-elevated and is NOT in a high risk flood zone (flood insurance not mandatory). Very private. No HOA!

4 Beds ⋅ 6 Baths

Just 5-miles outside historic St. Michaels, MD...Classic "Eastern Shore Waterfront Retreat," featuring a substantial 5,400+ sq. ft. home, thoughtfully designed to capture cooling SW summer breezes and spectacular sunset views across the sparkling waters of Harris Creek. Sited on 8.26 private acres w/over 300' of natural "living Shoreline," features of the brick home include high ceilings (including a cathedral ceiling in the family room and tray ceiling in the primary bedroom); four (or 5) bedrooms; 4 full and 2 half baths; large primary suite w/recently updated bath; gourmet kitchen w/island and breakfast room connected to a wonderful family room w/fireplace. Generous waterside glass to maximize the water views from most rooms. Beautiful waterside swimming pool (heated), surrounded by a spacious multi-level patio. For Chesapeake bay boating, there is a substantial 6' wide x 200' dock w/electric boat lift. Water depth at the dock on a typical low tide (MLW) is over 5 ft. This is a great boating, fishing and crabbing location. Tilghman Island's waterside restaurants, marinas and the open waters of Chesapeake Bay are just a short, scenic boat ride downstream from the dock. By car, the Town of St. Michaels with its many fine restaurants and attractions is less than 10-minutes away (5-miles). The house is well-elevated and is NOT in a high risk flood zone (flood insurance not mandatory). Very private. No HOA!

9262 Macks Lane, Mcdaniel

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$2,600,000

Welcome to your private Eastern Shore retreat! This amazing 4-bedroom, 4.5-bath Cape Cod is perfectly situated on a secluded peninsula, offering unparalleled tranquility and breathtaking waterfront views of Boone Creek located in beautiful Oxford, Maryland. The home offers an incredible blend of traditional elegance and modern luxury. An open and airy floor plan is bathed in natural light, with expansive windows framing the stunning water views from nearly every room. The living room has beautiful brick floors and a wood burning fireplace. You will also find a gas fireplace in the spacious family room. The bright and inviting sunroom has cathedral ceilings and walls of glass doors with water, pool, garden and patio views. The gourmet kitchen is a chef's delight, featuring high-end appliances, custom cabinetry, and a large center island. It flows effortlessly into the formal dining area which includes an additional fireplace for cozy and intimate dining experiences. Beautiful hard wood floors flow into several rooms. The main floor also hosts two private sanctuaries: an ensuite bedroom and a primary bedroom, each with private decks offering stunning water views. The primary suite's closet is a truly incredible, separate dressing room. A laundry room, a full bath, and a half bath complete the main level. Upstairs, two large bedrooms and a shared bath provide comfort and privacy for guests or family. Outside you discover a true entertainer's paradise. The property's unique peninsula location offers a wide expanse of water frontage, perfect for enjoying the Eastern Shore lifestyle. A large, sparkling in-ground pool is the centerpiece of the manicured grounds, surrounded by extensive hardscaping and lush landscaping, creating a resort-like feel. The detached two-car garage is enormous. There are raised beds in a fully fenced garden with a garden shed. The climate-controlled dock house offers endless possibilities for a gym, office, art studio or storage. The private dock provides water access for boating, kayaking, paddleboarding, fishing and crabbing on Boone Creek. With quick water access to Choptank River, Tred Avon River, Chesapeake Bay & Miles River, you can explore the best areas of the shore. This home is more than a residence; it's a lifestyle. Located just minutes from the historic town of Oxford, you'll have easy access to charming shops, restaurants, parks, the beach strand and the Oxford-Bellevue Ferry. This is a rare opportunity to own a piece of paradise on the Eastern Shore.

4 Beds ⋅ 5 Baths

Welcome to your private Eastern Shore retreat! This amazing 4-bedroom, 4.5-bath Cape Cod is perfectly situated on a secluded peninsula, offering unparalleled tranquility and breathtaking waterfront views of Boone Creek located in beautiful Oxford, Maryland. The home offers an incredible blend of traditional elegance and modern luxury. An open and airy floor plan is bathed in natural light, with expansive windows framing the stunning water views from nearly every room. The living room has beautiful brick floors and a wood burning fireplace. You will also find a gas fireplace in the spacious family room. The bright and inviting sunroom has cathedral ceilings and walls of glass doors with water, pool, garden and patio views. The gourmet kitchen is a chef's delight, featuring high-end appliances, custom cabinetry, and a large center island. It flows effortlessly into the formal dining area which includes an additional fireplace for cozy and intimate dining experiences. Beautiful hard wood floors flow into several rooms. The main floor also hosts two private sanctuaries: an ensuite bedroom and a primary bedroom, each with private decks offering stunning water views. The primary suite's closet is a truly incredible, separate dressing room. A laundry room, a full bath, and a half bath complete the main level. Upstairs, two large bedrooms and a shared bath provide comfort and privacy for guests or family. Outside you discover a true entertainer's paradise. The property's unique peninsula location offers a wide expanse of water frontage, perfect for enjoying the Eastern Shore lifestyle. A large, sparkling in-ground pool is the centerpiece of the manicured grounds, surrounded by extensive hardscaping and lush landscaping, creating a resort-like feel. The detached two-car garage is enormous. There are raised beds in a fully fenced garden with a garden shed. The climate-controlled dock house offers endless possibilities for a gym, office, art studio or storage. The private dock provides water access for boating, kayaking, paddleboarding, fishing and crabbing on Boone Creek. With quick water access to Choptank River, Tred Avon River, Chesapeake Bay & Miles River, you can explore the best areas of the shore. This home is more than a residence; it's a lifestyle. Located just minutes from the historic town of Oxford, you'll have easy access to charming shops, restaurants, parks, the beach strand and the Oxford-Bellevue Ferry. This is a rare opportunity to own a piece of paradise on the Eastern Shore.

4500 Boone Creek Road, Oxford

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: .

$2,600,000

‘Eagle’s Nest’ is an exceptional waterfront retreat overlooking Island Creek, just minutes from historic Oxford. Prime location with guest house and deep water (6.5' MLW). Privately sited on more than four acres amid mature trees and meticulously landscaped grounds, this impressive main residence (5324 SF)—completely rebuilt by Ilex Construction in 2008—offers four bedrooms, four full baths, and two half baths. Every room is generously sized and thoughtfully designed to capture expansive water views while providing elegant yet comfortable living. The main level features beautifully appointed living spaces, including a formal living room with coffered ceiling, wood-burning fireplace, custom built-ins, wet bar, and sliding doors opening to the waterside patio. A formal dining room, enclosed by French doors, offers an inviting setting for entertaining. At the heart of the home, the gourmet kitchen showcases a cathedral ceiling, large center island, top-of-the-line appliances, gas fireplace, spacious walk-in pantry, and custom built-ins—creating a warm and functional gathering space. The adjoining sunroom is filled with natural light and features vaulted ceilings, slate tile flooring, and sweeping water views, with glass doors opening to the patio and pool area. Nearby, a well-equipped mudroom, laundry room, and half bath add everyday convenience, along with a covered breezeway to the two-car garage. The desirable main-level primary suite serves as a private retreat with tranquil water views, dual walk-in closets, and a luxurious en suite bath. Just off the primary suite corridor, a private office with custom built-ins and an additional powder room enhance the home’s thoughtful design. Upstairs, three generously sized guest bedrooms each include en suite baths. A comfortable sitting area opens to a balcony overlooking Island Creek—an ideal place to relax and take in the serene setting. In addition, a coveted one-bedroom, one-and-a-half-bath guest house (968 SF) includes a full kitchen, living room, and attached two-car garage—perfect for visitors, extended family, or flexible use. Outdoor living is equally impressive, highlighted by a gunite swimming pool, expansive brick patio, mature landscaping, and extensive hardscaping designed to complement the waterfront setting. The private pier features two slips and a boat lift with 6.5' MLW along a protected, riprapped shoreline. ‘Eagle’s Nest’ presents a rare opportunity to enjoy refined Eastern Shore waterfront living just moments from Oxford. New roof on main house (2025). New pool cover: Aqua pool service contract paid for-2026

4 Beds ⋅ 6 Baths

‘Eagle’s Nest’ is an exceptional waterfront retreat overlooking Island Creek, just minutes from historic Oxford. Prime location with guest house and deep water (6.5' MLW). Privately sited on more than four acres amid mature trees and meticulously landscaped grounds, this impressive main residence (5324 SF)—completely rebuilt by Ilex Construction in 2008—offers four bedrooms, four full baths, and two half baths. Every room is generously sized and thoughtfully designed to capture expansive water views while providing elegant yet comfortable living. The main level features beautifully appointed living spaces, including a formal living room with coffered ceiling, wood-burning fireplace, custom built-ins, wet bar, and sliding doors opening to the waterside patio. A formal dining room, enclosed by French doors, offers an inviting setting for entertaining. At the heart of the home, the gourmet kitchen showcases a cathedral ceiling, large center island, top-of-the-line appliances, gas fireplace, spacious walk-in pantry, and custom built-ins—creating a warm and functional gathering space. The adjoining sunroom is filled with natural light and features vaulted ceilings, slate tile flooring, and sweeping water views, with glass doors opening to the patio and pool area. Nearby, a well-equipped mudroom, laundry room, and half bath add everyday convenience, along with a covered breezeway to the two-car garage. The desirable main-level primary suite serves as a private retreat with tranquil water views, dual walk-in closets, and a luxurious en suite bath. Just off the primary suite corridor, a private office with custom built-ins and an additional powder room enhance the home’s thoughtful design. Upstairs, three generously sized guest bedrooms each include en suite baths. A comfortable sitting area opens to a balcony overlooking Island Creek—an ideal place to relax and take in the serene setting. In addition, a coveted one-bedroom, one-and-a-half-bath guest house (968 SF) includes a full kitchen, living room, and attached two-car garage—perfect for visitors, extended family, or flexible use. Outdoor living is equally impressive, highlighted by a gunite swimming pool, expansive brick patio, mature landscaping, and extensive hardscaping designed to complement the waterfront setting. The private pier features two slips and a boat lift with 6.5' MLW along a protected, riprapped shoreline. ‘Eagle’s Nest’ presents a rare opportunity to enjoy refined Eastern Shore waterfront living just moments from Oxford. New roof on main house (2025). New pool cover: Aqua pool service contract paid for-2026

4573 Bringman Farm Road, Oxford

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

Selling Office: .

$2,600,000

Generational Waterfront Farm. Magnificent Building site on the Miles River on 50+ acres. Private tree-lined driveway passing through productive fields, mature evergreen and deciduous trees. There is a brick cape cod on the property and an outbuilding that should be considered a footprint for future development. Existing well, pier and bulkhead area on the cove (Newcomb Creek). Over 1500 of shoreline. 4 miles from St. Michaels and 5 miles from Easton. Incredible Sunrises and Sunsets, Remarkable true point of land with panoramic views, great waterfowl and deer hunting. Property includes large block of woods on other side of Rt 33 (approx.. 30+ acres). Owner has approval to be hooked up to public Sewer!

3 Beds ⋅ 3 Baths

Generational Waterfront Farm. Magnificent Building site on the Miles River on 50+ acres. Private tree-lined driveway passing through productive fields, mature evergreen and deciduous trees. There is a brick cape cod on the property and an outbuilding that should be considered a footprint for future development. Existing well, pier and bulkhead area on the cove (Newcomb Creek). Over 1500 of shoreline. 4 miles from St. Michaels and 5 miles from Easton. Incredible Sunrises and Sunsets, Remarkable true point of land with panoramic views, great waterfowl and deer hunting. Property includes large block of woods on other side of Rt 33 (approx.. 30+ acres). Owner has approval to be hooked up to public Sewer!

26396 St Michaels Road, Newcomb

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$2,500,000

205 Cherry Street is one of the most prestigious addresses in historic St. Michaels. Originally built as a single-family residence, it currently operates as an Inn. It is being marketed both as a 7 bedroom inn and also as a single family residence, offering 5 bedrooms (including the first floor primary bedroom suite). The original living room/office with fireplaces on the first floor are currently being used as bedrooms for the inn but can easily be converted back to living areas. (see virtual images in photos). The beautiful front lawn provides a park-like setting with one-of-a-kind water-views overlooking St. Michaels Harbor. There is also a 2 bedroom, 2 bath guest cottage on the property. The property directly across the street (FKA The Hambeleton Inn) was purchased as a private residence and serves as a second home to its owner. This is a wonderful opportunity to own a landmark historic inn or primary or second home in the heart of St. Michaels.

5 Beds ⋅ 9 Baths

205 Cherry Street is one of the most prestigious addresses in historic St. Michaels. Originally built as a single-family residence, it currently operates as an Inn. It is being marketed both as a 7 bedroom inn and also as a single family residence, offering 5 bedrooms (including the first floor primary bedroom suite). The original living room/office with fireplaces on the first floor are currently being used as bedrooms for the inn but can easily be converted back to living areas. (see virtual images in photos). The beautiful front lawn provides a park-like setting with one-of-a-kind water-views overlooking St. Michaels Harbor. There is also a 2 bedroom, 2 bath guest cottage on the property. The property directly across the street (FKA The Hambeleton Inn) was purchased as a private residence and serves as a second home to its owner. This is a wonderful opportunity to own a landmark historic inn or primary or second home in the heart of St. Michaels.

205 Cherry Street, Saint Michaels

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

Selling Office: .

$2,500,000

Welcome to ‘Drake’s Landing’! Beautifully sited on 20 picturesque acres on the shores of Irish Creek, this 4,602 sq. ft .completely renovated (2021) waterfront estate offers the perfect blend of casual elegance and thoughtful design. The main level welcomes with expansive water views and features a guest bedroom with ensuite bath, a cozy family room (or den/office), and a gracious living room anchored by a large brick hearth and woodburning fireplace. The gourmet kitchen is the center of the home - outfitted with upgraded appliances, a center island with breakfast bar, and additional dining space. Adjacent is a second kitchen - ideal for effortless indoor/outdoor entertaining. A formal dining room and large waterside sunroom complete the main living spaces. Upstairs, two spacious primary suites anchor each end of the home, offering privacy and comfort, with two additional guest bedrooms (one with ensuite bath) and a hall bath in between. Step outside to enjoy westerly water views from the elevated deck, or gather on the enclosed screened porch, perfect for crab feasts and sunset dining. Outdoor amenities include a charming 2BR/1.5BA guest cottage (540 sq. ft.), a new dock with two slips, stunning waterside pool, waterside firepit, and barrel sauna. A 3-bay equipment garage is connected to an enclosed game room and workshop - creating a complete retreat for relaxation, recreation, and unforgettable waterfront living. The property with its acreage is also great for hunting. This is Eastern Shore living at its best – spacious, serene, and set up for year-round enjoyment. *Furnishings may be available for sale.

5 Beds ⋅ 6 Baths

Welcome to ‘Drake’s Landing’! Beautifully sited on 20 picturesque acres on the shores of Irish Creek, this 4,602 sq. ft .completely renovated (2021) waterfront estate offers the perfect blend of casual elegance and thoughtful design. The main level welcomes with expansive water views and features a guest bedroom with ensuite bath, a cozy family room (or den/office), and a gracious living room anchored by a large brick hearth and woodburning fireplace. The gourmet kitchen is the center of the home - outfitted with upgraded appliances, a center island with breakfast bar, and additional dining space. Adjacent is a second kitchen - ideal for effortless indoor/outdoor entertaining. A formal dining room and large waterside sunroom complete the main living spaces. Upstairs, two spacious primary suites anchor each end of the home, offering privacy and comfort, with two additional guest bedrooms (one with ensuite bath) and a hall bath in between. Step outside to enjoy westerly water views from the elevated deck, or gather on the enclosed screened porch, perfect for crab feasts and sunset dining. Outdoor amenities include a charming 2BR/1.5BA guest cottage (540 sq. ft.), a new dock with two slips, stunning waterside pool, waterside firepit, and barrel sauna. A 3-bay equipment garage is connected to an enclosed game room and workshop - creating a complete retreat for relaxation, recreation, and unforgettable waterfront living. The property with its acreage is also great for hunting. This is Eastern Shore living at its best – spacious, serene, and set up for year-round enjoyment. *Furnishings may be available for sale.

5440 Ferry Neck Road, Royal Oak

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

Selling Office: .

$2,495,000

This exceptional waterfront cottage is set on two private acres and offers sweeping sunset views over the Choptank River to the Chesapeake Bay. Completely renovated from crawl space to roof, the home features over 2,600 square feet of beautifully finished living space with three bedrooms and three full baths. The interior showcases renovated kitchen and baths, complemented by extensive custom finish-work throughout. There is a detached garage with metal roof and second floor storage and gravel circular driveway with ample parking. Improvements on this home include an encapsulated crawl space, new roof, siding, multiple premium sliding glass doors and windows, all valuable upgrades that enhance both style and energy efficiency. The grounds have been thoughtfully transformed with curated shrubs, trees, and perennials that highlight the existing landscape, concrete pool, and pergola, creating an ideal setting for outdoor relaxation and entertaining. Enjoy easy boating access just 10 minutes to Oxford and 15 minutes to Tilghman, while by land the property is ideally situated between Easton and St. Michaels. Enjoy the protection of high property elevation (no flood insurance required) with a sturdy rip-rapped shoreline, beautiful sandy bottom, and a private L pier with two new boat lifts. 24878 W. Ferry Neck Road offers the perfect blend of privacy, comfort, and Eastern Shore waterfront living on the Choptank River. List of the many recent improvements in document section of this listing.

3 Beds ⋅ 3 Baths

This exceptional waterfront cottage is set on two private acres and offers sweeping sunset views over the Choptank River to the Chesapeake Bay. Completely renovated from crawl space to roof, the home features over 2,600 square feet of beautifully finished living space with three bedrooms and three full baths. The interior showcases renovated kitchen and baths, complemented by extensive custom finish-work throughout. There is a detached garage with metal roof and second floor storage and gravel circular driveway with ample parking. Improvements on this home include an encapsulated crawl space, new roof, siding, multiple premium sliding glass doors and windows, all valuable upgrades that enhance both style and energy efficiency. The grounds have been thoughtfully transformed with curated shrubs, trees, and perennials that highlight the existing landscape, concrete pool, and pergola, creating an ideal setting for outdoor relaxation and entertaining. Enjoy easy boating access just 10 minutes to Oxford and 15 minutes to Tilghman, while by land the property is ideally situated between Easton and St. Michaels. Enjoy the protection of high property elevation (no flood insurance required) with a sturdy rip-rapped shoreline, beautiful sandy bottom, and a private L pier with two new boat lifts. 24878 W. Ferry Neck Road offers the perfect blend of privacy, comfort, and Eastern Shore waterfront living on the Choptank River. List of the many recent improvements in document section of this listing.

24878 W Ferry Neck Road, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$2,435,000

DREAMING OF A BEACH HOUSE ? STUNNING LOCATION , ENDLESS BREEZES AND SUNSETS..... A treasure of vantage points and chic contemporary beauty, this Martingham waterfront retreat offers rare front-row views of Miles River happenings - including the historic Log Canoe Races, Fourth of July fireworks, daily passages of billowing sails,and, on crisp days, sightlines stretching for miles. Set on 2.32 acres with nearly 250 feet of sandy shoreline, life here moves with effortless rhythm; from morning beachfront strolls to afternoons shaped by regattas, summer pool partiesand in-town finds. Relax by the awe inspiring extra large 50 foot heated pool with jacuzzi with of space for sunbathing and relaxing. There is also a IGLUCRAFT sauna from Eastonia for the health concious resident. Within your home of contemporary coastal personality, 2,875 square feet are serene and elevated as walls of airy hues allow gridless-windows to compose ever-changing artwork of golden sunsets, lifting fog, and distant gliding hulls. Built-ins display collected shells and photographs from travels, while a glowing hearth anchors conversation with holiday guests. Spend unhurried Sundays in the landscaped-wrapped screened-in porch. Here, dream-up recipes for the weekend’s gatherings, while the kitchen’s updated stone surfaces and appliances prepare everything from perfect picnics to generous crab feasts. At day’s end, two and a half modern baths soothe, partnering with a main-level primary suite and two additional bedrooms—including airy loft. serving as a 4th bedroom. From your 125-foot pier with 8–10 feet MLW, welcome the seasonal residents that live on the Osprey platform, launch kayaks toward the picturesque edges of Long Haul Creek or set sail into the open reaches of the Chesapeake Bay. While on tour, spot sea glass along the shore, linger at the pier, and imagine the ease of your two-car garage. The dock - built by WHEEMS - offers 2 jet ski lifts, a 16K pound boatlift, electric and water and a platform area to sit over the water and relax . From home, St. Michaels charms just minutes away, where beloved shops, dining, and harbor life fill easy afternoons, while rounds at The Links at Perry Cabin, cycling routes, and scenic trails shape the days between. The roof has been replaced by MARASUN in 2022, new HVAC in 2021, pool build in 2022, new water heater 2023.

3 Beds ⋅ 3 Baths

DREAMING OF A BEACH HOUSE ? STUNNING LOCATION , ENDLESS BREEZES AND SUNSETS..... A treasure of vantage points and chic contemporary beauty, this Martingham waterfront retreat offers rare front-row views of Miles River happenings - including the historic Log Canoe Races, Fourth of July fireworks, daily passages of billowing sails,and, on crisp days, sightlines stretching for miles. Set on 2.32 acres with nearly 250 feet of sandy shoreline, life here moves with effortless rhythm; from morning beachfront strolls to afternoons shaped by regattas, summer pool partiesand in-town finds. Relax by the awe inspiring extra large 50 foot heated pool with jacuzzi with of space for sunbathing and relaxing. There is also a IGLUCRAFT sauna from Eastonia for the health concious resident. Within your home of contemporary coastal personality, 2,875 square feet are serene and elevated as walls of airy hues allow gridless-windows to compose ever-changing artwork of golden sunsets, lifting fog, and distant gliding hulls. Built-ins display collected shells and photographs from travels, while a glowing hearth anchors conversation with holiday guests. Spend unhurried Sundays in the landscaped-wrapped screened-in porch. Here, dream-up recipes for the weekend’s gatherings, while the kitchen’s updated stone surfaces and appliances prepare everything from perfect picnics to generous crab feasts. At day’s end, two and a half modern baths soothe, partnering with a main-level primary suite and two additional bedrooms—including airy loft. serving as a 4th bedroom. From your 125-foot pier with 8–10 feet MLW, welcome the seasonal residents that live on the Osprey platform, launch kayaks toward the picturesque edges of Long Haul Creek or set sail into the open reaches of the Chesapeake Bay. While on tour, spot sea glass along the shore, linger at the pier, and imagine the ease of your two-car garage. The dock - built by WHEEMS - offers 2 jet ski lifts, a 16K pound boatlift, electric and water and a platform area to sit over the water and relax . From home, St. Michaels charms just minutes away, where beloved shops, dining, and harbor life fill easy afternoons, while rounds at The Links at Perry Cabin, cycling routes, and scenic trails shape the days between. The roof has been replaced by MARASUN in 2022, new HVAC in 2021, pool build in 2022, new water heater 2023.

24830 Deepwater Point Drive, Saint Michaels

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

Selling Office: .

$2,405,000

Waterfront living at its finest in Pirate’s Cove, tucked along the serene waters of Trippe Creek. Set on 2.71 waterfront acres and beautifully sited across from a nature preserve, this property offers serenity, sophistication, and sweeping water views. Built in 1986 and thoughtfully reimagined with a custom renovation in 2016, the home blends elegant design and modern comforts in a meticulously maintained, one-level layout featuring three bedrooms and three full baths. Vaulted ceilings and walls of windows fill the living spaces with natural light, creating a bright, open atmosphere throughout. Overlooking the water, the gourmet kitchen is a chef’s delight, featuring a Wolf range with warming drawer, Sub-Zero refrigerator, double wall ovens, quartzite countertops, generous cabinetry, and a spacious island perfect for gathering. The living room, kitchen, and primary suite are all sun-drenched and open seamlessly to the deck, providing stunning water views and creating effortless indoor-outdoor living. The primary suite is a tranquil retreat with expansive water views, a large walk-in closet, and a spa-like en-suite bath highlighted by a stone soaking tub, glass-enclosed shower, and a unique laundry-chute window that connects directly to the laundry room for added convenience. Outside, enjoy summer days by the salt water, in-ground pool or stroll down to your private pier with approximately 4' MLW—ideal for boating, kayaking, or simply soaking in the peaceful setting. A large attached three-car garage provides ample space for vehicles, storage, and waterfront gear. This is the essence of Eastern Shore waterfront living—refined, relaxed, and ready to be enjoyed.

3 Beds ⋅ 3 Baths

Waterfront living at its finest in Pirate’s Cove, tucked along the serene waters of Trippe Creek. Set on 2.71 waterfront acres and beautifully sited across from a nature preserve, this property offers serenity, sophistication, and sweeping water views. Built in 1986 and thoughtfully reimagined with a custom renovation in 2016, the home blends elegant design and modern comforts in a meticulously maintained, one-level layout featuring three bedrooms and three full baths. Vaulted ceilings and walls of windows fill the living spaces with natural light, creating a bright, open atmosphere throughout. Overlooking the water, the gourmet kitchen is a chef’s delight, featuring a Wolf range with warming drawer, Sub-Zero refrigerator, double wall ovens, quartzite countertops, generous cabinetry, and a spacious island perfect for gathering. The living room, kitchen, and primary suite are all sun-drenched and open seamlessly to the deck, providing stunning water views and creating effortless indoor-outdoor living. The primary suite is a tranquil retreat with expansive water views, a large walk-in closet, and a spa-like en-suite bath highlighted by a stone soaking tub, glass-enclosed shower, and a unique laundry-chute window that connects directly to the laundry room for added convenience. Outside, enjoy summer days by the salt water, in-ground pool or stroll down to your private pier with approximately 4' MLW—ideal for boating, kayaking, or simply soaking in the peaceful setting. A large attached three-car garage provides ample space for vehicles, storage, and waterfront gear. This is the essence of Eastern Shore waterfront living—refined, relaxed, and ready to be enjoyed.

5728 Pirates Cove Road, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$2,300,000

Timeless Tidewater Colonial-inspired waterfront estate set on 3.5± private acres with 870± feet of shoreline and panoramic water views. A rare offering combining classic architecture, thoughtful upgrades and exceptional outdoor living in one of Talbot County’s most desirable waterfront settings, with a seamless indoor-outdoor flow and water views from nearly every room. Featured in Coastal Living, the residence reflects exceptional design and offers gracious living spaces, including four bedrooms with three updated en-suite baths and three fireplaces. A custom great room with wood-burning fireplace, built-ins and fine wood cabinetry anchors the home, complemented by formal living and dining rooms each with fireplaces. The gourmet custom kitchen includes custom cabinetry, quartz countertops, KitchenAid appliances and dual pantries. Outdoor amenities include a 30,000-gallon pool, expansive lawns, mature trees, irrigation system, partial rip-rapped shoreline and private pier with electric and water. Ideal for boating, kayaking, paddleboarding and waterfront entertaining, this exceptional property offers privacy, comfort and enduring Eastern Shore appeal. Two Osprey nesting platforms convery with the property. Some furniture available under separate contract. Boat Lift sold As Is. Do not come down driveway without an appointment.

4 Beds ⋅ 4 Baths

Timeless Tidewater Colonial-inspired waterfront estate set on 3.5± private acres with 870± feet of shoreline and panoramic water views. A rare offering combining classic architecture, thoughtful upgrades and exceptional outdoor living in one of Talbot County’s most desirable waterfront settings, with a seamless indoor-outdoor flow and water views from nearly every room. Featured in Coastal Living, the residence reflects exceptional design and offers gracious living spaces, including four bedrooms with three updated en-suite baths and three fireplaces. A custom great room with wood-burning fireplace, built-ins and fine wood cabinetry anchors the home, complemented by formal living and dining rooms each with fireplaces. The gourmet custom kitchen includes custom cabinetry, quartz countertops, KitchenAid appliances and dual pantries. Outdoor amenities include a 30,000-gallon pool, expansive lawns, mature trees, irrigation system, partial rip-rapped shoreline and private pier with electric and water. Ideal for boating, kayaking, paddleboarding and waterfront entertaining, this exceptional property offers privacy, comfort and enduring Eastern Shore appeal. Two Osprey nesting platforms convery with the property. Some furniture available under separate contract. Boat Lift sold As Is. Do not come down driveway without an appointment.

3770 Leonard Cove Lane, Trappe

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

Selling Office: .

$2,300,000

135 +/- acres bordering Easton town limits.

29833 Dover Road, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: .

$2,200,000

This exquisite in-town St. Michaels coastal-style waterfront is a designer’s dream home. The 3,300 sq, ft. residence shows like a new model home with an unparalleled quality of finishes and level of design. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the ever-popular St. Michaels Nature Trail offering an easy walk or bike ride to the wonderful shops, restaurants and amenities of Historic St. Michaels. The residence features four private bedroom suites, a den, 4.5 spa-like bathrooms and a 2-car garage with an adorable guest residence with outdoor deck above. A 1.5-acre manicured lush, landscaped setting features a beautiful saltwater, waterside pool, substantial outdoor entertaining space and a firepit. The property also features a custom, stone entrance with lighting, a tree lined Belgian block bordered driveway and a fully irrigated sprinkler system. The home enjoys a bright, sunlit, open floor plan, sophisticated finishes, tall ceilings, a main level waterside primary suite, and a beautiful kitchen designed for entertaining that includes quartz counters, a glass subway tile backsplash and stainless appliances. The living room features a fireplace wall with limestone surround, custom cabinetry and floating shelving. The home’s appointments include; high-end bath fixtures and lighting by Restoration Hardware, beautiful bamboo hardwood flooring, custom frameless glass shower enclosures, an upgraded sound system on the main level and pool entertainment deck and automated blinds. The dream garage is temperature controlled, has epoxy flooring and a custom cabinetry and storage system. Enjoy boating on the picturesque San Domingo Creek and the connecting, beautiful tributaries via the dedicated pier that is shared with the adjacent neighbor that features, an approximate 4 feet MLW water depth, a 10,000 lb. boat lift and a floating pier for your kayaks. Your family and guests will enjoy the convenience and lifestyle of this coveted St. Michaels location and the waterfront living experience afforded by this exquisite residence. **See the movie icon for the virtual tour and floor plans.

4 Beds ⋅ 5 Baths

This exquisite in-town St. Michaels coastal-style waterfront is a designer’s dream home. The 3,300 sq, ft. residence shows like a new model home with an unparalleled quality of finishes and level of design. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the ever-popular St. Michaels Nature Trail offering an easy walk or bike ride to the wonderful shops, restaurants and amenities of Historic St. Michaels. The residence features four private bedroom suites, a den, 4.5 spa-like bathrooms and a 2-car garage with an adorable guest residence with outdoor deck above. A 1.5-acre manicured lush, landscaped setting features a beautiful saltwater, waterside pool, substantial outdoor entertaining space and a firepit. The property also features a custom, stone entrance with lighting, a tree lined Belgian block bordered driveway and a fully irrigated sprinkler system. The home enjoys a bright, sunlit, open floor plan, sophisticated finishes, tall ceilings, a main level waterside primary suite, and a beautiful kitchen designed for entertaining that includes quartz counters, a glass subway tile backsplash and stainless appliances. The living room features a fireplace wall with limestone surround, custom cabinetry and floating shelving. The home’s appointments include; high-end bath fixtures and lighting by Restoration Hardware, beautiful bamboo hardwood flooring, custom frameless glass shower enclosures, an upgraded sound system on the main level and pool entertainment deck and automated blinds. The dream garage is temperature controlled, has epoxy flooring and a custom cabinetry and storage system. Enjoy boating on the picturesque San Domingo Creek and the connecting, beautiful tributaries via the dedicated pier that is shared with the adjacent neighbor that features, an approximate 4 feet MLW water depth, a 10,000 lb. boat lift and a floating pier for your kayaks. Your family and guests will enjoy the convenience and lifestyle of this coveted St. Michaels location and the waterfront living experience afforded by this exquisite residence. **See the movie icon for the virtual tour and floor plans.

962 San Domingo Court, Saint Michaels

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

Selling Office: .