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luxury real estate for sale Queenstown, United States

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House Queenstown (United States)

From the moment you turn onto winding Carmichael Road and cross the bridge onto Wye Island, the pace begins to slow. Of the island’s approximately 2,800 acres, only about 350 are privately owned. The State of Maryland through the Maryland Park Service owns and manages the rest. ‘The Point’ is among the island’s handful of private properties, distinguished by almost six acres and more than 1,200 feet of elevated waterfront, one of the largest private shorelines on Wye Island, with over half riprapped. Set at the end of a private drive, this exceptional estate offers a rare sense of privacy amid the island’s pristine, unspoiled lands. The main residence is distinctive in both design and setting, with a playful modern aesthetic, soaring ceilings reaching nearly 18 feet, and an open floor plan oriented toward the water. Two bedroom suites occupy the main level, each with an ensuite bath and its own exceptional outlook, one overlooking the Wye River, the other facing a private cove. Upstairs, two additional bedrooms share a Jack-and-Jill bath, with each opening to its own private deck. Designed for both everyday living and memorable family gatherings, the property embraces the natural beauty of its surroundings. An outdoor kitchen creates an inviting setting for entertaining, while the approximately 90-foot pier, with an estimated 5’+ mean low water, provides direct access to the river and the Chesapeake beyond. A private duck blind and abundant wildlife further connect the property to the land and water. A charming guest house provides comfortable accommodations for extended family and friends, with a kitchenette, bedroom, full bath, and sweeping water views. A second-floor loft, with exceptional views across the river and surrounding farmland, provides an ideal setting for a home office, studio, or quiet retreat. Life on Wye Island is defined by its unspoiled landscape and enduring connection to the outdoors. The island is celebrated for its quiet coves, abundant wildlife, and sporting traditions, with opportunities for boating, crabbing, fishing, waterfowl hunting, and deer hunting. Here, days can be spent on the river, along the shoreline, in the surrounding woods and fields, or simply enjoying the remarkable sense of privacy that comes with living in such a protected setting. Meticulously maintained and ready for its next chapter, The Point represents an increasingly rare opportunity to own a private waterfront estate in one of the Eastern Shore’s most pristine and unspoiled settings. A place for family and friends to gather, enjoy the water, and experience all that Wye Island and Eastern Shore have to offer. ***Owner occupied - PLEASE DO NOT DRIVE DOWN DRIVEWAY.*** Agent related to Owner.

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$3,850,000
5bedrooms
4bathrooms
land 2.4ha

By Ttr Sotheby's International Realty

50

Contemporary house with pool and terrace Queenstown (United States)

Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

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$4,995,000
5bedrooms
5bathrooms
land 7.3ha

By Ttr Sotheby's International Realty

50
Video

House Queenstown (United States)

Welcome to 200 Wye Road, an exceptional waterfront estate set on over two private acres along the Wye River, directly across from the protected natural beauty of Wye Island. Here, scale, setting, and thoughtful design converge to create a truly elevated Eastern Shore lifestyle. Spanning more than 8,100 square feet across three finished levels, the residence offers a refined yet highly livable floor plan designed to capture water views from nearly every room. Expansive living spaces, a formal dining room with handpainted custom wallpaper from the U.K., and a reimagined gourmet kitchen create an environment equally suited for everyday living and large-scale entertaining. The kitchen has been thoughtfully redesigned with updated cabinetry, statement lighting, and a full suite of premium appliances, including Wolf, Sub-Zero, and Bosch. The home offers exceptional flexibility, including an optional first-floor primary suite, a dedicated home gym, two laundry rooms, and an oversized mudroom designed for seamless day-to-day living. Two wood-burning fireplaces add warmth and character, enhancing the home’s sense of comfort and timeless appeal. The primary suite serves as a private retreat, complete with two walk-in closets and a fully renovated, spa-inspired bath featuring heated flooring, a soaking tub, a glass-enclosed shower, and its own gas fireplace, delivering a level of comfort and detail rarely found. Since 2024, the property has undergone extensive upgrades that enhance both performance and long-term value, including a new Owens Corning roof with a transferable warranty, three fully replaced Trane HVAC systems, a whole-home water filtration system, and comprehensive renovations throughout the bathrooms and interior spaces. Outdoor living is where the property truly distinguishes itself. A newly renovated 20x40 waterfront pool with a pebble finish and automatic cover anchors the setting, complemented by expansive hardscaping, manicured grounds, and multiple areas designed for entertaining or quiet relaxation. The shoreline has been improved with 250 feet of stone rip rap, and the deep-water dock is outfitted with new electrical service and lighting, featuring a new 25,000 lb boat lift and a 12,000 lb one along with two additional slips, providing effortless access to the Wye River and beyond. Whether enjoying sunrise coffee on the screened porch, hosting summer gatherings by the pool, or heading out by boat to St. Michaels or the Kent Narrows, this property offers a lifestyle defined by ease, privacy, and connection to the water. Conveniently located in Queenstown, just minutes from shopping, dining, and Route 50, with easy access to Annapolis and Easton, 200 Wye Road represents a rare opportunity to own a turnkey waterfront estate in one of the Eastern Shore’s most sought-after settings.

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$4,700,000
6bedrooms
6bathrooms
land 9,267

By Ttr Sotheby's International Realty

88 listings near Queenstown

Nearby
50

Apartment with terrace Saint Michaels (United States)

Whether you are looking for a full-time residence, weekend retreat, or investment property, this unit is truly move-in ready. Situated in Martingham community just minutes from St. Michaels, shops, restaurants 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. Additionally, the deck was also recently primed and painted. 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. Come and enjoy the St. Michaels lifestyle today.

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$385,000
2bedrooms
3bathrooms

By Ttr Sotheby's International Realty

Nearby
50
Video

House Easton (United States)

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

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$13,750,000
5bedrooms
9bathrooms
land 140.2ha

By Ttr Sotheby's International Realty

Nearby
50

Property Grasonville (United States)

Discover the perfect blend of modern elegance and comfort in this stunning Colonial-style home located in the desirable Perry's Retreat. Built in 2024, this residence boasts a pristine condition and an array of features designed to enhance your lifestyle. Step inside to find an inviting open floor plan that seamlessly connects the gourmet kitchen, dining area, and family room, creating an ideal space for entertaining and everyday living. The kitchen is a chef's dream, equipped with upgraded countertops, a double oven, built-in microwave, and ample pantry space. With four generous bedrooms and 2.5 baths, this home offers plenty of space for relaxation and privacy. The upper floor laundry adds convenience to your daily routine, while the elegant luxury vinyl plank flooring and tasteful window treatments throughout elevate the aesthetic. Outside, the property features a well-maintained exterior with sidewalks and a concrete driveway leading to a two-car attached garage, ensuring ample parking and easy access. The 0.14-acre lot provides a manageable outdoor space for gardening or leisure activities. This home is not just a place to live; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this exquisite property your own!

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$619,900
4bedrooms
3bathrooms
land 567

By Ttr Sotheby's International Realty

Nearby
38

House Grasonville (United States)

Welcome home to 120 Pathfinder Circle in Perry's Retreat! Built in 2023 and meticulously maintained, this 4 -bedroom , 3.5 bath home offers approximately 3,010 sf of beautify designed living space, where thoughtful upgrades,custom touches,and everyday functionality come together. From the moment you walk in, the attention to detail is impossible to miss. The main level showcases a stunning three-sided fireplace topped with a custom walnut mantel - an eye catching centerpiece that makes the living space feel warm, inviting, and distinctly your own. The kitchen is made for gathering, cooking and entertaining, featuring two ovens and custom -made pendant lighting that adds both function and personality. Throughout the home, an upgraded Craftsman trim package recessed lighting , luxury vinyl plank flooring, and ceiling fans in every room create a polished, comfortable feel. With Ethernet wiring throughout , this home is ready for everything from work from home days to movie nights and streaming marathons. Upstairs, the spacious primary suite feels like a retreat, complete with two walk in closets and a generous shower with dual showerheads. A secondary bedroom with its own ensuite bath offers a private space for guests or family. Two additional flex spaces give you the freedom to create dedicated offices, home gym, playroom or whatever your lifestyle demands. A separate loft adds even additional room to spread out. The back yard is where this property really shines. The 16x40 patio provides an incredible outdoor living and entertaining space, while the privacy fence creates a comfortable, secluded setting. The meticulously maintained landscaping and lush lawn are true standouts and add exceptional curb appeal. With a three car garage, there's plenty of room for vehicles and storage. This is more than a newer home - it's a home that has been thoughtfully enhanced and lovingly maintained. The custom details and flexible spaces truly make it feel special. Come see why 120 Pathfinder Circle is the home you have been looking for.

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$659,950
4bedrooms
4bathrooms
land 0.1ha

By Monument Sotheby's International Realty

Nearby
50

House Saint Michaels (United States)

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. This exceptional residence was recently featured in The Talbot Spy–view in the virtual tour section or the link below. https://bit.ly/4zqt09f

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$1,950,000
3bedrooms
3bathrooms
land 1,659

By Ttr Sotheby's International Realty

Nearby
48
Video

Contemporary house with pool and garden Easton (United States)

Welcome to Holly House – A Rare Waterfront Legacy Estate on the Miles River Holly House presents an extraordinary opportunity to own one of the Upper Miles River’s most captivating waterfront estates. Set gracefully on five spectacular, beautifully landscaped acres, this contemporary French-inspired residence offers approximately 150 feet of private shoreline, panoramic water views, and unforgettable sunsets. Designed for effortless one-level living, the impeccably constructed brick home blends timeless architecture with endless potential. The current residence features a gracious living room, formal dining room, inviting den, spacious kitchen, sunroom, private office, study/optional bedroom, an elegant waterfront primary suite with dual bathrooms and separate walk-in closets, two additional en-suite bedrooms, a powder room, unfinished basement, and an attached two-car garage. Outdoor living is equally impressive. A waterside 8-foot-deep swimming pool, expansive terrace overlooking the Miles River, private 150-foot pier, tennis court, and oversized outbuilding create an exceptional setting for entertaining, recreation, and peaceful waterfront living. Whether you choose to thoughtfully refresh the existing home or create a spectacular new estate, Holly House offers an unmatched canvas to realize your vision. The property has also received its long-awaited approval from Talbot County for a new 5-6 bedroom septic system, allowing construction to begin immediately. Fully permitted architectural and structural plans, along with a stunning full-color exterior fly-through video, are included with the sale. For those wishing to personalize the design, the approved plans can be modified to reflect a buyer’s individual style and lifestyle needs. This is more than a home—it’s a once-in-a-generation opportunity to create a landmark waterfront estate in one of the Eastern Shore’s most coveted location See document panel for floor plans for large addition and another for one level living

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$2,995,000
3bedrooms
5bathrooms
land 2ha

By Ttr Sotheby's International Realty

Nearby
50

House with pool Saint Michaels (United States)

Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant harbor, boutique shops, and award-winning restaurants. Enter from the wide, covered front porch - ideal for morning coffee or greeting neighbors - into a grand, elongated foyer that sets a welcoming tone. The interior features gorgeous hardwood floors throughout, seamlessly connecting the bright living spaces. This home offers four spacious bedrooms, generously sized bathrooms, and ample storage, providing comfort for family and guests alike. The rear yard is a private retreat designed for both relaxation and entertaining. Tucked into the lush landscaping (which includes an in-ground irrigation system) is a fully finished, detached accessory building. This versatile, light-filled structure is perfect for a dedicated craft studio, hobby workshop, private home office, or fitness room. This property also includes rare, highly coveted off-street parking. Situated just steps from San Domingo creek and less than a block from Talbot Street, the house provides quick access to the waterfront park/kayak launch and the nature trail as well to the town's maritime attractions, local ice cream parlors, and fine dining. An 1850 historic treasure in a premier in-town location doesn't come along often-schedule your private tour today and make the magic of the Eastern Shore your reality.

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$1,195,000
4bedrooms
4bathrooms
land 0.1ha

By Ttr Sotheby's International Realty

Nearby
39
Video

House Saint Michaels (United States)

NEW PRICE!! 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.

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$695,000
3bedrooms
2bathrooms
land 0.1ha

By Ttr Sotheby's International Realty

Nearby
50

House with pool and terrace Saint Michaels (United States)

Waterfront Living Reimagined in San Domingo Cove! Coastal influences, exceptional craftsmanship and meticulous attention to detail define this immaculate custom waterfront home. Dramatic two-story family room, soaring ceilings, walls of windows and an open staircase with stainless steel cable railings create a striking architectural statement. The second-story catwalk and loft overlook the main living area, while expansive windows frame the pool and water views beyond. Designed for both everyday living and entertaining, the chef's kitchen features quartz countertops, stainless steel appliances and extensive soft-close cabinetry. An oversized island provides generous prep space and seating, while the bright eat-in dining area and separate beverage station offer exceptional space for casual dining and entertaining. Bamboo flooring extends throughout the living spaces, adding warmth and continuity to the home's contemporary coastal design. The thoughtfully designed floor plan includes a first-floor primary suite overlooking the pool and San Domingo Creek, two additional ensuite bedrooms and a spacious bonus room with a full bath, ideal as a guest suite, home office, studio, media room or fourth bedroom. Outside, beautifully landscaped grounds frame the waterside pool and expansive patio, while the shared private pier with a boat lift and floating dock provides easy access for boating, kayaking and paddleboarding. An oversized three-car garage offers ample space for vehicles, storage and recreational equipment. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the St. Michaels Nature Trail. This distinctive property combines waterfront privacy with convenient access to the shops, restaurants, marinas and waterfront attractions of St. Michaels.

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$2,395,000
4bedrooms
5bathrooms
land 0.6ha

By Ttr Sotheby's International Realty

Nearby
Contract pending
50
Video

House Chester (United States)

Designed to rival a private resort, this waterfront estate was built for celebrating with family and friends. Sweeping Chesapeake views set the stage for every gathering. The waterfront pool features a cascading rock waterfall, a tucked in bench, and a generous sun shelf, all overlooked by a pool house with a covered summer kitchen, bar, seating area, and full bath with AC. A curated firepit lounge, expansive patios and balconies, and a screened waterside porch bring indoor and outdoor living together for every occasion. At the shoreline, life on the Bay begins, with an expansive private beach perfect for wading, sandcastles, and quiet evenings by the water. The newly expanded L shaped pier stretches 260 feet and is engineered for serious boating, with dockage for a large yacht, 24,000 lb. and 10,000 lb. lifts, electric, R/O water, dual pedestals, and decorative lighting. Protected waters offer calm conditions for docking, fishing, crabbing, and watersports, with direct Bay access and easy cruising to Annapolis, St. Michaels, and beyond. A circular driveway centered by a gorgeous fountain leads to the entry, where a stunning two story foyer and grand staircase greet you, framed by spectacular water views. The great room features a soaring wall of glass and a fireplace, opening to a chef's kitchen appointed with Wolf and Sub Zero appliances, custom cabinetry, a conversation bar, pantry, and breakfast nook. The dining room seats twelve or more, ready for every holiday feast. The primary suite is a private waterfront retreat, with a sitting area beneath a domed ceiling, a fireplace, custom built ins, and a spa bath with heated floors, a jetted soaking tub, and a multi head shower. The waterfront game room offers a fireplace, wet bar, and large TV, while the private theater seats eight in front of a 100 inch screen, making this home the destination for family and friends year round. Upstairs, five architecturally unique bedrooms, three ensuite, include private waterfront balconies and a large activity room opening to a deck overlooking the pool, dock, creek, and bay. A fully equipped in law suite offers its own kitchen, living area, bedroom, fireplace, and attached two car garage, while a separate heated and cooled four car garage with porcelain tile and custom cabinetry serves as studio, workshop, or gym. Six fireplaces, Anderson and Palladian windows, tankless water heaters, a whole house water softener and reverse osmosis system, a 60KW whole house generator, and fiberoptic 2.5GB internet with seventeen access points bring comfort and connectivity throughout. Fully app based control manages lighting, HVAC, security, pool, spa, generator, music, locks, and network, inside and out. Tucked along a quiet private road with easy access to the Bay Bridge, Annapolis, and Washington D.C., this is waterfront vacation living designed to be experienced every day. Serenity Lane describes how you feel, not just where you are. Welcome home.

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$5,400,000
7bedrooms
9bathrooms
land 1ha

By Ttr Sotheby's International Realty

Nearby
50
Video

House with pool Saint Michaels (United States)

PRICE IMPROVEMENT.... PRIVATE Estate Living Minutes from Historic St. Michaels... Escape to nearly twenty acres of unspoiled countryside just moments from the charm and waterfront allure of historic St. Michaels. This 4,492-square-foot home offers refined comfort with four bedrooms, two and a half baths, and a gourmet kitchen designed for both everyday living and effortless entertaining. A dedicated space for a future elevator adds thoughtful flexibility for years to come. Outside, the possibilities are as expansive as the land itself- 19.5 private acres with pastures suited for up to eleven Horses, plus a car barn for storage, hobbies, or collections. Agricultural and livestock production also permitted (buyers should confirm specifics with Easton P&Z). Notably, 5.75 wooded acres are enrolled in the DNR's Forest Stewardship Plan, preserving the agricultural tax discount without the requirement to grow crops or house livestock.

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$2,000,000
4bedrooms
3bathrooms
land 7.9ha

By Ttr Sotheby's International Realty

Nearby
9

Land Bozman (United States)

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.

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$800,000
72,196

By Ttr Sotheby's International Realty

Nearby
6

Land Bozman (United States)

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.

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$800,000
29,583

By Ttr Sotheby's International Realty

Nearby
6

Land Bozman (United States)

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.

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$800,000
42,411

By Ttr Sotheby's International Realty

Nearby
30

House Stevensville (United States)

NEW PRICE! Don't miss this opportunity to live on the water in a beautiful neighborhood! Tucked between the tranquil waters of Long Creek and Shipping Creek, this approximately 2,100 square-foot waterfront retreat offers a rare blend of mid-century charm and modern comfort. With two bedrooms, an office and three full bathrooms, there's plenty of space to live, relax, and host with ease. Originally built in 1977 and thoughtfully renovated in 2019, the home showcases timeless mid-century design - clean lines, an inviting flow, and character you can't replicate in new construction. A brand-new well pump (2025) adds peace of mind, ensuring reliable, efficient water service for years to come. The primary bedroom offers a true private retreat, while the additional bedrooms and full baths provide comfort and flexibility for family or guests. Throughout the home, updated finishes and smart design touches create a space that feels both stylish and easy to live in. Step outside and the real magic begins: your own private dock on Long Creek, with a mean depth of approximately 6 feet, ideal for kayaking, paddleboarding, fishing, or simply pulling up the boat after a day on the water. Enjoy the birds, sea life and mature landscaping from morning to night! This is more than a house - it's a lifestyle. Mid-century character, recent upgrades, and an unbeatable waterfront setting come together to create a truly special place to call home.

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$1,150,000
181
2bedrooms
3bathrooms

By Annonceur International

Nearby
50

Property Easton (United States)

Set on 2.85 waterfront acres with panoramic views of Dixon Creek along the coveted Easton–St. Michaels corridor, this beautifully renovated coastal home offers over 5,000 square feet of light-filled living space with 4+ bedrooms, 5 full baths, and 1 half bath. Originally built in 1964 and thoughtfully transformed, the home blends timeless waterfront appeal with refined coastal style, featuring shiplap accents, hardwood flooring, vaulted beamed ceilings, custom built-ins, and expansive windows showcasing breathtaking water views throughout. Designed for both everyday living and effortless entertaining, the open floor plan includes a gourmet kitchen with top-tier appliances, a waterside breakfast nook, spacious dining area, inviting living room with woodburning fireplace, and a separate billiard room with its own woodburning fireplace. Filled with natural light, the main living spaces flow seamlessly from one room to the next, creating an inviting atmosphere for intimate gatherings. The main-level primary suite serves as a private retreat, complete with luxurious ensuite bath and large walk-in closet. Two separate upper-level wings provide exceptional accommodation for family and guests. One wing offers three bedrooms, served by an ensuite bath and a shared hall bath. The opposite wing features an expansive bonus room with custom built-in bunks, a full bath, and abundant space for recreation, overflow guests, or private guest quarters. Stunning water views and thoughtfully designed built-ins enhance many of the home's living spaces. At the heart of this exceptional waterfront retreat, thoughtfully designed outdoor spaces invite you to embrace the relaxed elegance of Eastern Shore living. Enjoy a screened porch overlooking the water, gunite pool, heated spa, expansive slate patio, outdoor kitchen, arbor-covered sitting area, fire pit, outdoor shower with full bath facilities, and beautifully landscaped grounds. Additional improvements include an attached 2-car garage with generous storage space and a storage shed. The private pier is equipped with a floating dock, two boat lifts, two slips, and approximately 4’ MLW, providing access to Dixon Creek and beyond for boating, fishing, kayaking, and exploring the surrounding waterways. The property is currently operating as a successful vacation rental. Showings during the summer season are limited to turnover days and approved availability. Sellers prefer a November 2026 settlement.

… 
$3,250,000
5bedrooms
6bathrooms
land 1.2ha

By Ttr Sotheby's International Realty

Nearby
50

Property with pool and garden Easton (United States)

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

… 
$2,195,000
4bedrooms
4bathrooms
land 9,348

By Ttr Sotheby's International Realty

Nearby
50
Video

House with pool Wittman (United States)

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.

… 
$5,995,000
8bedrooms
6bathrooms
land 31.2ha

By Ttr Sotheby's International Realty

Nearby
50
Video

House with pool Wittman (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.

… 
$7,900,000
8bedrooms
6bathrooms
land 46.4ha

By Ttr Sotheby's International Realty

Nearby
50
Video

House with pool Wittman (United States)

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.

… 
$5,995,000
8bedrooms
6bathrooms
land 31.2ha

By Ttr Sotheby's International Realty

Nearby
50
Video

Farmhouse with outbuildings and garden Wittman (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. 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.

… 
$7,900,000
8bedrooms
6bathrooms
land 46.4ha

By Ttr Sotheby's International Realty

Nearby
35
Video

House with pool Chester (United States)

Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs, the spacious primary suite features a sitting area, two walk-in closets, and en-suite bath, alongside three additional bedrooms and two full bathrooms. The unfinished walkout basement includes a rough-in for a future bath. Outside, enjoy a fenced backyard complete with a patio and built-in fire pit—perfect for gathering year-round. Community amenities include swimming pool, clubhouse, fitness center, walking trails, community pier, picnic area, and kayak launch. Centrally located on Kent Island. Only 5 minutes to the Bay Bridge.

… 
$825,000
4bedrooms
4bathrooms
land 0.1ha

By Ttr Sotheby's International Realty

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