luxury real estate for sale Sherwood, United States

Bolton Farm, available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. An adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

Bolton Farm, available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. The adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. Bolton Farm, available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. Bolton Farm, available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

This exceptional 17.84-acre parcel of land offers a rare opportunity to embrace an exclusive lifestyle. With an impressive 360 +/- feet of waterfront along the picturesque Sandy Point Cove leading to Broad Creek, this property is a haven for privacy. Enjoy private access to the water, ideal for fishing, canoeing, and kayaking. The expansive lot offers ample space for the creation of a luxurious retreat, with approved plat, perc, and SDA. Located in the Bozman area of Talbot County, a short drive beyond Saint Michaels. Vandenberg Lane is a private road, shared by multiple neighbors.

This exceptional 10.48 acre parcel of land offers a rare opportunity to embrace an exclusive lifestyle. With an impressive 461+/- feet of waterfront along the picturesque Sandy Point Cove leading to Broad Creek, this property is a haven for privacy. Enjoy private access to the water, ideal for fishing, canoeing, and kayaking. The expansive lot offers ample space for the creation of a luxurious retreat, with approved plat, perc, and SDA. Located in the Bozman area of Talbot County, a short drive beyond Saint Michaels.

This exceptional 7.314-acre parcel of land offers a rare opportunity to embrace an exclusive lifestyle. With an impressive 562 +/- feet of waterfront along the picturesque Sandy Point Cove leading to Broad Creek, this property is a haven for privacy. Enjoy private access to the water, ideal for fishing, canoeing, and kayaking. The expansive lot offers ample space for the creation of a luxurious retreat, with approved plat, perc, and SDA. Located in the Bozman area of Talbot County, a short drive beyond Saint Michaels.

PRICE IMPROVEMENT*** Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor living. Enjoy your morning coffee while watching boats drift by, or relax in the evening with views that will take your breath away. The home is located in a sought-after waterfront community offering fantastic amenities including a clubhouse, pool, and marina—perfect for boating, entertaining, and leisure. Whether you’re looking for a peaceful full-time residence or a weekend retreat, this home checks all the boxes. Just bring your boat and your dreams! NEW ROOF & FIREPLACE 2024, NEW APPLIANCES 2019

Set on 19.5 private acres just minutes from historic waterfront Saint Michaels, this exceptional 4,492 sq ft residence offers the perfect blend of space, privacy, and convenience. The home features four bedrooms and two and a half baths, with expansive living areas ideal for both everyday living and entertaining, including a well-appointed chef's kitchen. The thoughtfully designed layout includes a designated space for a future elevator, adding flexibility and long-term convenience. A separate car barn provides ample storage for vehicles, hobbies, or workshop space. Enjoy the nicely fenced rear patio area, perfect for outdoor relaxation or entertaining. Surrounded by peaceful countryside yet close to the charm, dining, and waterfront attractions of downtown Saint Michaels, this property presents a rare opportunity to enjoy Eastern Shore living at its finest. **Note the forest area behind the house has been put into the DNR's Forest Stewardship Plan which allows the home owner to keep the AG tax discount without having to grow crops and/or livestock.

Welcome to 107 E. Chestnut, a beautifully restored circa-1870 residence nestled in the heart of St. Michaels. From the moment you step inside, you are greeted by the perfect blend of timeless character and modern sophistication, where original architectural details have been thoughtfully preserved and seamlessly integrated with extensive renovations. The spacious entry combines an elegant living and dining area, featuring wood floors, a gas fireplace flanked by custom built-ins, and custom shutters have been added to each window. Throughout this home you will find historic charm and craftsmanship are evident at every turn. At the rear of the home is a full bath and designer kitchen that opens to the family room highlighted by soaring ceilings and an abundance of windows that fill the space with natural light year round. This inviting area flows to the screened-in porch and brick patio, creating the perfect setting for indoor-outdoor living. Beyond the patio lies a garden oasis featuring lush landscaping, colorful perennials, pond and large detached shed/storage building. The current owner has worked with the Town of St. Michaels to obtain approvals for converting this structure into a separate guest suite, and architectural plans are available for the next owner. The second level offers two generously sized bedrooms and a beautifully redesigned full bath. The rear bedroom includes an overlook of the family room, which offers additional space that could easily be transformed into a private sitting area, dressing room or walk-in closet. The front bedroom features a dedicated dressing room and oversized closet, providing the potential to create an en-suite bath. Both rooms offer cathedral ceilings with exposed rafters adding to the rooms architectural interest and charm. This is a true gem in historic St. Michaels that includes off street parking. Don't miss this exceptional opportunity to own a home in the one of the most popular towns on the Eastern Shore.

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.

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.

Thoughtfully reimagined from the studs out, this exceptional residence offers the character of an in-town cottage with the quality, comfort, and finishes of a newly constructed home. Every detail has been carefully considered, creating a seamless blend of timeless charm and modern design. A welcoming front porch with a classic porch swing sets the tone before stepping inside to a light-filled interior featuring soaring vaulted ceilings and an open-concept floor plan designed for effortless everyday living and entertaining. Rich hardwood flooring flows throughout, complemented by a beautifully appointed chef’s kitchen, three well-proportioned bedrooms, and two elegantly finished full baths—all conveniently situated on a single level. Virtually every component of the home has been renewed, allowing the next owner to enjoy a truly turnkey property with the peace of mind that comes with comprehensive renovation. Outside, professionally designed landscaping surrounds a private backyard, creating a tranquil setting for outdoor dining, entertaining, or quiet relaxation. Ideally located in the heart of St. Michaels, the home is just moments from the town’s renowned boutiques, acclaimed restaurants, waterfront parks along the Miles River, the community pool, and the YMCA. Offering the rare combination of like-new construction and one of Maryland’s most desirable small-town settings, 803 New Lane presents an exceptional opportunity to enjoy Eastern Shore living at its finest.

Welcome to Mostly Porches an exceptional coastal retreat with captivating views of the harbor, perfectly situated on a spacious .41 acre corner lot just around the corner from the shops and restaurants of St. Michaels. Built in 2018 with virtually maintenance-free construction, this beautifully designed home offers the ideal blend of comfort, style, and convenience in a rare St. Michaels setting. Inside the floor plan is filled with an abundance of natural light and enhanced by soaring cathedral ceilings, creating an airy and inviting atmosphere ideal for both every day living and perfect for entertaining. The main living area incorporates the living, dining and kitchen and offers easy access to the extensive porches the home features, including the screened-in porch with a gas fireplace and views of the harbor. In the great room there is also a hidden pantry along the dining area wall with plenty of shelving and storage. Custom built-in bookcases line the living area wall to the left of the propane fireplace which incorporates a built-in 90 lb per day nugget ice-maker. The gourmet kitchen is centered around a large island and features SS Thermador appliances including a duel fuel range with a six burner gas cooktop and electric oven, and an under counter wine fridge and under counter beverage fridge in the island. The contemporary design features the primary suite, 2nd bedroom, office/den, full bath and utility closet all on the main level. A standout out feature of this property is the 2nd level private guest suite, which is a licensed income-producing vacation rental, offering flexibility for guest or the opportunity for supplemental income. This private enclave includes a small sitting area, private bath and kitchenette with under counter refrigerator drawer, under counter freezer drawer, Keurig coffee maker, counter top microwave, and free standing shelves. The property also includes an attached 2 car garage, fire pit, raised garden beds with drip irrigation, and full irrigation system in the yard plus an oversized attached 2 car garage. With its desirable location close to all St. Michaels has to offer, exceptional amenities, and low-maintenance design, this is a rare opportunity to own one of the town's newer build homes with water views and income producing opportunity.

Situated in the established community of Martingham, and surrounded by the Links at Perry Cabin golf course, this beautifully updated 2-bedroom, 2.5 bath townhome has been thoughtfully renovated with an emphasis on quality craftsmanship, energy efficiency, and long-term durability. The redesigned open floor plan creates a seamless flow throughout the main living areas, complemented by updated cabinetry, granite countertops, and stainless steel appliances in the kitchen. All three bathrooms have been refreshed with new vanities, fixtures, and finishes, offering a clean and modern feel throughout the home. Beyond the cosmetic updates, extensive infrastructure improvements provide peace of mind, including a newer HVAC, upgraded electrical panel, full outlet and switch replacement and enhanced attic efficiency with resealing and R49 insulation installation. Interior finishes have been completely reimagined and updated throughout, including new luxury vinyl plank flooring on the upper level and premium Mohawk carpeting with upgraded padding in the lower bedrooms and on the stairwell (2024). Fresh interior paint throughout the home, along with meticulous restoration of original doors - stripped, primed, and repainted with all new hardware installed in 2024 - add to the home's character and detail. Additional improvements include a new washer and dryer (2024), new sliding glass doors in the bedrooms, and a 60-inch Hunter ceiling fan in the great room. A stand out feature of this unit is the expanded floor plan, offering a more open, functional, and spacious living area not commonly found in similar units. The HOA recently completed significant improvements, including a new roof, decking replacements, and new gutters in 2025. Completely turnkey and thoughtfully upgraded make this property ideal as a full-time residence, weekend retreat or investment property.

Set on 20 private waterfront acres with over 800 feet of shoreline along the Chesapeake Bay, this extraordinary estate offers a rare opportunity to own one of Maryland’s most impressive legacy properties. Behind a gated entrance and winding tree-lined drive, the residence combines timeless architecture, exceptional craftsmanship, and resort-inspired amenities designed for both grand entertaining and everyday enjoyment. The shoreline is simply remarkable, featuring riprap protection, a private pier with lifts, sandy beach areas, water and electric service, and panoramic Bay views that deliver spectacular sunsets year-round. Whether enjoying a quiet morning by the water, setting out for a day on the Bay, or gathering with family and friends for an evening by the fire, every aspect of the property has been thoughtfully designed to embrace the waterfront lifestyle. Inside, over 15,000 square feet of finished living space showcases Brazilian cherry flooring, handcrafted millwork, coffered ceilings, custom paneling, seven fireplaces, and beautifully curated living spaces throughout. The gourmet kitchen serves as the heart of the home, featuring premium appliances, an oversized island, sunlit breakfast room, and a fully equipped butler’s pantry designed for seamless entertaining. The residence offers two luxurious primary suites, including a main-level retreat with fireplace, spa-inspired bath, private office, and direct access to the waterfront. Multiple ensuite guest bedrooms, a theater room, game room, exercise suite, expansive third-floor recreation space, and a private apartment above the garage provide exceptional flexibility for hosting family and guests. Outdoor amenities rival those of a private resort. Enjoy a saltwater pool and spa, covered poolside entertaining pavilion with outdoor kitchen and fireplace, regulation tennis and pickleball court, expansive patios and terraces, fire pit, pond with fountain, playground, and extensive professional landscaping that creates a setting of complete privacy and tranquility. This is more than a home—it is a Chesapeake Bay estate designed for generations to gather, celebrate, and create lasting memories. A rare offering where luxury, privacy, recreation, and waterfront living come together on an extraordinary scale.

Set along the peaceful shores of Chews Creek, this beautifully renovated waterfront home delivers the quintessential Eastern Shore lifestyle, where spectacular sunsets, endless water views, and effortless indoor-outdoor living take center stage. Thoughtfully updated throughout, the home offers five bedrooms and four full baths with a layout designed for both comfortable everyday living and exceptional entertaining. Hardwood floors flow throughout the main level, while abundant natural light and an open floor plan create a bright, inviting atmosphere. At the heart of the home, the gourmet kitchen features a large center island, Silestone countertops, Sub-Zero refrigerator, Viking gas cooktop, Miele built-in espresso maker, beverage refrigerator, nugget ice maker, stainless steel appliances, and ample space for gathering with all your guests. The kitchen opens seamlessly to the living and entertaining spaces, all oriented to capture beautiful water views. The main level offers tremendous versatility with a first-floor bedroom, dedicated office space, formal dining room accented by designer wallpaper, and an elegant living room with fireplace. A spacious waterside family room provides the perfect setting to relax, entertain, and enjoy the ever-changing waterfront scenery. Upstairs, the waterside primary suite serves as a private retreat overlooking the creek. Additional guest accommodations include generously sized bedrooms and a large bunk room ideal for hosting family and friends. Beautifully renovated baths feature custom tile work, dual vanities, and oversized walk-in showers. Outdoor living is equally impressive. A large waterside deck overlooks the heated and cooled salt-water swimming pool, creating a resort-like setting for summer gatherings. The outdoor amenities also feature a private outdoor spa/hot tub for year-round enjoyment. Professionally landscaped grounds, mature plantings, and multiple outdoor entertaining areas enhance the property’s relaxed waterfront lifestyle. Additional highlights include a detached two-car garage with an additional office space/bonus room,, roof less than ten years old, updated finishes throughout, and a setting that showcases some of the most breathtaking sunset views on Maryland’s Eastern Shore. Whether enjoying a quiet evening by the pool, entertaining guests on the deck, or watching the sun disappear over the water, this exceptional waterfront property offers a rare opportunity to experience Kent Island living at its finest.

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. Co-listed by Rob Lacaze of TTR Sotheby's International Realty and Janet Larson of Benson and Mangold.

Brand New Home Ready for Move-In! Step into this stunning two-story home designed for modern living, offering the perfect blend of style, comfort, and functionality. The open-concept layout features upgraded lighting, hardware, and railings throughout, complemented by a premium exterior color package. The gourmet kitchen includes a large island, walk-in pantry, and stainless steel appliances, flowing seamlessly into a bright and spacious family area ideal for entertaining. The main level features a private primary suite with a luxurious en suite bath, along with a convenient half bath and laundry room. Upstairs, you'll find three additional bedrooms and two full baths, providing plenty of space for family or guests. Located in Lakeside at Trappe, just minutes from Easton and Cambridge, this amenity-rich community offers a pool, fitness room, and dog park.

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

Set on 28 private acres overlooking Plaindealing Creek along the desirable Easton–St. Michaels corridor, this beautifully remodeled waterfront home offers 4 bedrooms, 4 full baths, and breathtaking panoramic views stretching across to Oxford, the Choptank River, and beyond. Positioned on an exceptional point of land, the property enjoys a rare combination of expansive water vistas, privacy, and direct access to some of the Eastern Shore’s finest boating and sporting waters. A scenic, tree-lined drive leads to the residence, where the water immediately takes center stage. Thoughtfully renovated in 2019, with numerous additional upgrades completed in subsequent years, the home is designed for both relaxed everyday living and effortless entertaining. The main level features a waterside primary suite with an exquisite ensuite bath, along with an additional guest bedroom and adjacent full bath(with sauna). The spacious living room is anchored by a brick fireplace with pellet stove insert, custom built-ins, and sliding doors opening to the waterside patio, creating a seamless connection to the remarkable setting. A well-appointed kitchen with stainless steel appliances and granite countertops adjoins the separate dining room, where spectacular water views provide a memorable backdrop for gatherings. Two other main-level rooms offer flexibility for an office, family room, exercise room, or other living needs, while a generous laundry room with built-ins and a secondary staircase adds everyday convenience. Upstairs are two additional guest bedrooms and two en-suite baths along with an adjoining bonus room ideal for guests or hobbies, and a second staircase. A true sportsman’s paradise, the property offers deep water, excellent fishing, private hunting, and endless opportunities for boating and recreation. The private pier, completed in 2023, features three slips, a boat lift, and a jet ski lift. With approximately 7' MLW, a newly riprapped shoreline, sandy beach, new BAT septic system installed in 2019, and a new roof completed in 2026, this exceptional waterfront retreat is perfectly suited for those seeking the very best of Eastern Shore living. *Approximately 24 acres are enrolled in a Forest Stewardship Plan. * Please do not drive in without an appointment-security monitoring.

This is a true coastal retreat, from its stunning exterior to its thoughtfully designed living spaces. A one-of-a-kind waterfront estate, the property offers more than 2,000 feet of shoreline and sits on 5.4 private acres at the end of Kilby Point. Surrounded by water on both the Wye River and Eastern Bay, this exceptional home captures endless panoramic views in every direction. And yes-how many people can say they own a lighthouse? The home has been completely renovated down to the studs, blending timeless coastal charm with modern convenience. Interior features include shiplap walls, beamed ceilings, new flooring, and beautifully reimagined living spaces throughout. The new kitchen is a showpiece, featuring quartz countertops, a large island, and Caf appliances. A sprinkler system has also been added for peace of mind. Designed to maximize its breathtaking setting, the home offers multiple living and entertaining spaces, including a game room, office, and dramatic 360-degree rooms with incredible views of the surrounding water and wildlife. There are four bedrooms, five full baths, and two half baths, all fully renovated with walk-in showers, elegant tile work, and stylish vanities. The primary suite is especially luxurious, featuring separate his-and-hers bathrooms. Outdoor features are just as impressive, with a sand beach, rip-rapped shoreline, private pier with lift and electric, new pool decks, and a private setting that feels both peaceful and extraordinary. Additional upgrades include new siding, rails, septic, and a redesigned garage that has been incorporated into the home's layout with glass doors, creating even more functional living space. If you are searching for a waterfront property that feels truly special-distinctive, private, and unforgettable-this is it.

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

Discover the rare opportunity to own one of the Eastern Shore's finest waterfront parcels: Lot 5, an exceptional 4.18-acre homesite in the exclusive Morgan's Point community of Oxford, Maryland. This home site has an approved prec, and flood insurance is not required. Tucked along the serene Tred Avon River, this buildable waterfront gem offers expansive privacy and boundless potential, thanks to its generous scale and direct river access with 389 feet of rip-rap shoreline. Perfect for your custom estate, family compound, or legacy retreat, this sanctuary marries natural splendor with the refined charm of Talbot County's coastal haven. Spanning 4.18 acres, a fully usable lot provides versatile space to build your future home with breathtaking river vistas. Boasting direct frontage on the Tred Avon River with ample mean low water depth In a market where waterfront estates command premiums, this rare 4+ acre offering represents an unparalleled canvas for your vision. Nestled in the tranquil town of Oxford, this estate offers privacy and serenity while remaining conveniently close to shopping, dining, entertainment, medical facilities, and the Chesapeake Bay. Major commuter routes provide easy access to Washington, DC; Northern Virginia; Annapolis; and Philadelphia, with four major airports: BWI (71 miles), DC (74 miles), Dulles (112 miles), and Philadelphia (113 miles). Embrace the Eastern Shore lifestyle and live the Bay Life in unparalleled luxury!