luxury houses for sale Dukes County, United States

You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main house was recently renovated by a top local contractor and the result is a rustic Vineyard vibe with a sophisticated twist. The cozy and comfortable kitchen and sitting room areas lead to the dramatic Great Room on the north end of the house - the 600 square foot space with its 26’-high ceilings is bathed in light thanks to the banks of windows and French doors. There are two bedroom suites upstairs with views of the main pond, one of them with a sundeck. The third floor loft area has also been used as a bedroom and is the perfect spot to accommodate younger members of the family and their friends. The detached two-story guest quarters continue the Vineyard country chic theme with a delightful bedroom with veranda overlooking a separate area of the property from the main house. In addition to the main house and detached guest bedroom, there is a barn with a large finished room and loft as well as a secluded writing studio. A new garage completes the compound. Note: Four-bedroom septic in place. Property currently has 3 bedrooms plus 1 loft sleeping space.

Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from all rooms while being just a short walk from the Association boat ramp and kayak storage. The main level features a living area with a wood-burning fireplace, a spacious kitchen, and a screened-in porch with cathedral ceilings, perfect for dining while enjoying the beautiful views. The primary suite is situated on the second floor and boasts French doors that open to a small deck, allowing you to take in the expansive scenery. The lower level includes three bedrooms, each with French doors leading to a lower deck, and they share a full bathroom. The Sengekontacket Association, established in 1971, encompasses 93 acres and provides a variety of amenities including tennis and pickleball courts, an Association Clubhouse situated on Wiggy’s Pond, and a boat ramp with kayak storage on Sengekontacket Pond. Homeowners can consult the Harbor Master for a mooring in Major’s Cove, where the Association dock is located. Fully renovated in 2007, this property is ready for you to enjoy!

Experience the serene beauty of this 4-bedroom, 3.5-bathroom pond-front home in the Sengekontacket Community. Nestled on a hillside overlooking a freshwater pond, this home offers the perfect island retreat. Lush garden beds and wildflowers greet you as you make your way to the pond, where you can enjoy swimming or paddling. The well-appointed kitchen seamlessly connects to the dining room and deck, all with stunning pond views. The first-floor primary bedroom features a private bath and a spacious closet, with sliding doors opening to the back deck. Upstairs, another ensuite bedroom awaits, along with an open loft ideal for an office or game room. The finished lower level opens to a bluestone patio with an outdoor shower and includes two bedrooms, a full bathroom, and a large laundry area. Residents of the Sengekontacket Community can take advantage of access to the dock and kayak storage on Sengekontacket Pond, as well as tennis/pickleball courts and a community clubhouse, perfect for hosting small events. Fully furnished, including kayaks and electric bikes, this property is ideal for a peaceful retreat, an investment, or both. All you need is your toothbrush!

Ocean views - Nestled on a quiet corner lot, this classic beach house offers a reverse floor plan and distant views of the Atlantic Ocean over the Katama Plain. It is only 1.5 miles to South Beach and just under 2 miles to the heart of Edgartown village. The upper level features the common living space including the dining area, kitchen, living room with fireplace, and large powder room. The lower level is where you find the more private spaces, including the primary bedroom suite plus an 2 additional bedrooms and full bathroom. For 30 years the property has been a generational meeting place for the owners, their family, and friends, and now they are passing the baton on to its future owners. Enjoy it “as is” or put your vision to work to create a brand new Katama beach house to make your own memories.

Gorgeous post-and-beam home built by a respected contractor. This spacious house plus detached guest quarters is on the outskirts of the village conveniently located on the way to South Beach. The property is at the end of a long driveway off Katama Road and is private and quiet. Upon arrival, you are greeted by beautiful landscaping with large beds of hydrangeas. There are 3 bedrooms in the main house, including on the first floor a large Great Room and a spacious primary bedroom suite. The living area spills out naturally onto a large fir deck. Upstairs is a secondary sitting area plus two bedrooms and a bath. There is a 2-bay garage with guest quarters upstairs. There is plenty of room for a swimming pool should the future owner want one. This is a comfortable home in the Katama Country style with lots of space for your family to make their own memories.

Abutting hundreds of acres of conservation land and walking trails leading to the second-highest point on Martha's Vineyard with views of the Elizabeth Islands, this classically-styled house with detached guest quarters offers 5 total bedrooms and 4 full baths plus an outdoor shower. The primary bedroom suite is a generous size and has its own small deck that overlooks the charming front yard. The property feels quintessentially Chilmark with ancient stone walls and mature plantings. The detached guest quarters features a spacious bedroom, full bath, kitchenette eating area, and a garage. Menemsha Hills Reservation is your backyard - 211 acres described by its Trustees as follows: Menemsha Hills was shaped by thousands of years of glacial advance and retreat. Today an array of mini-environments comprise a rugged, pleasant landscape: low wetlands, woodland groves leading to a hilltop, wind-blasted coastal plains, a rocky ocean edge, and 308-foot Prospect Hill. Not to mention - Menemsha sunsets are a short distance away!

This expansive historic compound in the heart of Edgartown village offers the perfect blend of old-world charm and modern luxury. Just steps away from Edgartown’s finest restaurants and shops, this stunning property has been completely renovated by Stern McCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details. Upon entering, you'll be greeted by a sophisticated interior with open-plan living spaces designed for easy entertaining. The main level features sleek modern furnishings, flowing from the kitchen and dining area through French doors to a beautifully landscaped outdoor patio, ideal for al fresco dining and relaxation. Beyond the patio, a lush lawn and manicured gardens surround an impressive 42' x 18' swimming pool, creating a true outdoor oasis. The second level houses four spacious bedrooms, including a luxurious primary suite with an office, ensuite bath, and a private deck overlooking the pool. The third floor offers a large sleeping area with six twin beds, a full bath, a game area, and French doors leading to a sun-drenched deck. Perfect for family living or hosting guests, this home combines historic character with the finest modern conveniences. Located on North Water Street, this light-filled property is an exceptional opportunity to own a one-of-a-kind retreat in one of Edgartown’s most desirable locations.

A landmark property located on the very northernmost tip of Martha's Vineyard. 1005 Main Street is one of the ''Four Sisters'' - the four grandest and most historic homes in the distinguished West Chop neighborhood. The setting is unparalleled with a large private beach and 210-degree views so expensive that you can enjoy both sunrises and sunsets from the same deck. The views are extremely dynamic with ferries and fishing boats passing in the distance, and at night, the twinkling of lights from the mainland. There are 8 large bedrooms, 7 full baths, and a 2-bedroom apartment in the lower level. The home still exudes olde worlde charm despite all 5,050 sq ft having been renovated between 1995 and 2022 with new insulation, roof, and HVAC system, and updated plumbing and electric. The 400 ft of private beach is a rare asset, and the boardwalk down to it has been trod by many who have come to love this home and incomparable setting. With its multiple decks and spectacular views, the home has always been a prime location for entertaining friends and family. Owners may inquire about membership at the nearby West Chop Club, which offers a wide range of amenities.

Mattakesett Bay Home - South Beach is the place to be, and this immaculate 3 level Mattakesett Bay Home (duplex) is nestled in the woods which is barely a half mile away. Open kitchen, living and dining area with powder room and laundry on the first level. Primary en suite with 2 additional bedrooms and full bathroom on second level. The loft which is accessed thru the primary bedroom has many uses either as a tv/den or sleeping area for overflow guests with half bath. Many owners enjoy nearby Edgartown Bay Road for morning bike rides or walks. In addition to the highly popular Atlantic Ocean beach nearby, there are all the facilities of the Mattakesett community close at hand, including a pool, tennis, basketball courts, and extensive children's programs. The Mattakesett rental program makes this a hassle-free income producer.

Experience the buzz of one of Katama's most desirable neighborhoods, right across from Down Harbor and next door to the Field Club and Somerset Lane. The good energy is everywhere. Here is your sanctuary amidst the hubbub, a custom-built 4700 sq ft classically styled home that feels brand new (square footage includes a finished basement). The vibe is upscale Edgartown with a coastal contemporary twist. The home is designed for entertaining an open floor plan transitions seamlessly to the stunning patio and landscaped backyard with a swimming pool and an outdoor kitchen beneath the pergola. The entryway provides a taste of things to come, with vaulted ceilings and an elegant stairway to the second floor. The chef's kitchen with top-of-the-line appliances has a large island with soapstone countertops that provides an area for casual gatherings or ample space for cooking. The substantial first-floor primary bedroom suite enjoys direct access to the deck and overlooks the backyard and pool area. Upstairs there are two large bedroom suites - plus a separate sitting area with fireplace and deck. The high ceilings provide light and openness in this elegant home. And as if all this space isn’t enough, there is a 1200 sq ft sq ft finished basement with a media room and two additional bonus rooms for overflow guests. The Carriage House is a revelation, as above the two-car garage there are spacious guest quarters with bold design choices that will appeal to your guests. At present there is a kitchenette that in 2 years zoning will allow to be expanded into a complete kitchen with a stove. A finished product home like this is not seen often in the Katama area.

This meticulously renovated 1920s gem is nestled in the desirable West Chop area of Vineyard Haven, offering a perfect blend of historical charm and modern luxury. With deeded access to a pristine beach on Vineyard Sound, this exquisite residence is a seaside haven. Step inside to discover a spacious layout. The heart of the home is the gourmet kitchen, boasting custom cabinetry and high-end appliances. Entertain with ease in the open-concept living and dining areas, where upgraded systems and central A/C ensure year-round comfort. The second floor features a primary bedroom suite with a luxurious tile bath and soaking tub in addition to 2 guest bedrooms and an elegantly appointed guest bath with laundry. Every detail of this home has been thoughtfully considered, including a charming compass rose stained glass window, adding a touch of nautical flair. The finished lower level includes additional living space and a spacious bedroom. Step outside to the stunning mahogany rear deck overlooking a newly landscaped yard, ideal for entertaining and an outdoor shower. With easy access to Downtown Vineyard Haven and Vineyard Sound beaches, don’t miss the opportunity to own this exceptional property where timeless beauty meets contemporary living.

This beautifully renovated gambrel-style home in Vineyard Haven seamlessly blends classic charm with modern luxury. This pristine residence is nestled within a private, hedge-lined yard in one of Vineyard Haven’s most quiet and quaint neighborhoods. With the new heated salt-water pool, outdoor shower, lovely plantings, and beautiful gardens, no detail has been overlooked. The property also features a renovated garage with a finished second level, perfect for a creative studio. Inside, the home exudes warmth and elegance, with wide pine flooring, custom craftsmanship, and intricate wood detailing on the ceilings. The spacious living room, centered around a gas fireplace, is both inviting and stylish. The sunlit kitchen, equipped with top-of-the-line appliances and refined finishes, includes a cozy window seat that adds to its charm. The primary bedroom suite offers a serene retreat, complete with a private tile bath and access to a 2nd-floor deck. The three additional bedrooms are equally comfortable and well-appointed, providing ample space for guests. The finished lower level expands your living space further, ideal for a home theater, gym, or playroom. Spend your days soaking in this privacy that this tranquil abode provides, or take advantage of its ideal location to access the hustle and bustle of downtown Vineyard Haven where you can enjoy various galleries, shops, and fine dining. This location is also convenient to Owen Park Beach, West Chop and Mink Meadows Golf Club.

Lamberts Cove Beach access, first and second floor water views, and a warm and inviting home in a private West Tisbury location - that is what is on offer here. The home was recently upgraded with a new kitchen and bathrooms. The primary bedroom suite has even better views than those from the first floor. The walkout lower level is a two bedroom suite with full bath, sitting area, kitchenette, and private entrance that leads to a beautiful sitting area beside a fenced-in vegetable garden and flower-cutting garden. In addition to a deck and backyard patio, there is also a porch in the front of the house. There is a climate-controlled garage that is currently a complete workshop with an upstairs that can be converted into a detached bedroom if one of the bedrooms in the main house is decommissioned.

Welcome to your ideal Edgartown retreat! This stunning classic cape-style home features four bedrooms and two baths. Built and cared for by a contractor, this residence exudes quality and attention to detail at every turn. Nestled on a picturesque half-acre lot in the Westminster Acres neighborhood, privacy abounds in this tranquil setting. Situated on a quiet paved dead-end street, enjoy easy access to all island amenities, including beaches, bike paths, state forests, and public transportation. Step inside to discover a bright and airy first floor, adorned with hardwood floors and a cozy fireplace. The spacious eat-in kitchen boasts stainless steel appliances and granite countertops, complemented by a slider leading to a sprawling deck overlooking manicured landscaping and gardens. On the first floor, you'll find a convenient bathroom and one bedroom, while the second floor hosts a generously sized primary bedroom with abundant natural light and a skylight. Two additional bedrooms and another full bathroom complete the second level, offering ample space for family and guests. Adding to the allure of this home is the expansive basement, spanning 890 sq. ft. and providing endless possibilities for storage, recreation, or future expansion. Don't miss out on the opportunity to make this exceptional Edgartown property your own.

Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within a reasonable distance from essential amenities and entertainment options. Whether you're looking for a year-round residence or a vacation getaway, this waterfront home in Squibnocket is an idyllic sanctuary to create unforgettable memories with family and friends.

This classic New England home is a true masterpiece of modern living. Nestled on a spacious and meticulously landscaped lot in Katama, this property offers the perfect blend of elegance, comfort, and convenience. The main house features three spacious and beautifully appointed bedrooms, each designed for relaxation and comfort. From the primary suite to the guest bedrooms, every room offers a serene retreat with ample natural light. The main living area is thoughtfully designed with an open concept layout, creating an ideal space for entertaining. A cozy fireplace and large windows enhance the ambiance, providing both warmth and captivating views of the lush surroundings. The french doors open to a deck overlooking the manicured lawn. A state-of-the-art media room, complete with comfortable seating, a large screen, and high-quality audio visual equipment. It's the perfect spot for movie nights, game days, or simply relaxing with friends and family along with a wine cellar just steps away. The carriage house features a three-car garage, providing ample space for your vehicles and storage needs including a large one bedroom and bath upstairs. Katama Bay View Road is located adjacent to Sheriffs Meadow Conservation land and public access to Katama Bay. Conveniently located near South Beach, one of Martha's Vineyard's most beautiful and sought-after beaches.

Welcome to your dream home in the exclusive Lower Makonikey Association, a serene enclave on Martha's Vineyard. This meticulously crafted 3,284 square-foot residence with a 3-car garage is a masterpiece of design and comfort, set on 3.21 acres of lush, tree-lined grounds accented by historic stone walls. Offering 4 spacious bedrooms and 4 elegantly appointed bathrooms, this home embraces the charm of island living. The main level features a flowing floor plan, ideal for both entertaining and everyday living, with a gourmet kitchen with a sun-filled breakfast nook, and butler’s pantry, dining room, and a spacious living room with a brick fireplace. A home office and laundry room finish the first floor which has beautiful hardwood floors throughout. Upstairs, the primary bedroom suite is beautifully appointed and features a spacious bathroom with double sinks, spa tub and shower. The bedrooms are generously sized, with ample natural light and stunning views of the surrounding landscape. The third level holds tremendous potential, offering the possibility to add 2 additional bedrooms, further enhancing the home's versatility. Outside, the back deck and expansive grounds provide a peaceful sanctuary, perfect for outdoor activities, gardening, or simply relaxing in nature's embrace. As a resident of the Lower Makonikey Association, you'll enjoy access to a private association beach on Vineyard Sound. This exceptional property is more than just a home; it's a lifestyle. Experience the perfect blend of privacy, elegance, and community in one of Martha's Vineyard's most sought-after neighborhoods.

Welcome to your dream retreat in Oak Bluffs—a magnificent eight-bedroom oceanview estate that combines luxury, space, and unparalleled views in one breathtaking offering. This property is designed to accommodate family and friends with ease while offering an elegant and serene environment for all to enjoy. The open floor plan of the main living areas ensures a seamless flow between the living room, dining room, and kitchen, making it perfect for entertaining. High ceilings and large windows flood the space with natural light and provide spectacular water views from every angle. The state-of-the-art kitchen is a chef's delight, featuring high-end appliances, ample counter space, and a large island that doubles as a breakfast bar. Custom cabinetry and elegant finishes complete this culinary haven. Each of the eight bedrooms is designed as a private sanctuary, offering comfort and tranquility. Most rooms feature ensuite baths and large windows that offer stunning water views, allowing you to wake up to the sight and sound of the gentle waves. In addition to the main living room, the property includes several cozy sitting areas, a media room for movie nights, and a game room, ensuring there's always a perfect spot for relaxation and entertainment. It's more than just a home; it's a sanctuary where you can create lasting memories with loved ones, enjoy sophisticated coastal living, and savor the unique charm of this beautiful area.

Two waterfront lots are part of this unique 4.40 acre offering - a 1.30 acre lot with a pre-existing four bedroom and three bathroom dwelling and a 3.10 acre vacant lot to build! This exquisite waterfront sanctuary boasts breathtaking views and serene surroundings on Katama Bay. The enchanting home offers ample space for comfortable living both indoors and outdoors. As you step through the front door, you are greeted by an airy and light-filled interior, flanked with windows, that seamlessly blend with the beauty of the outdoors. The spacious living area is perfect for hosting gatherings. The highlight of this home is the expansive porch where you can enjoy your morning coffee while taking in the picturesque views of the waterfront. Imagine relaxing here as you watch the sunset over the tranquil waters. Upstairs, you will find the inviting bedrooms, each offering a peaceful retreat at the end of the day. The primary suite is a true oasis with its own private balcony overlooking the water, creating the perfect spot for relaxation. Located in a highly desirable waterfront community on Chappy and just a short distance to Edgartown Village. Don't miss this rare opportunity to own a waterfront gem that offers a lifestyle of comfort, beauty and a unique opportunity to build your Chappy compound with the two lots. You can have up to nine bedrooms with town approval on the vacant land parcel!—sold as is.

Welcome to the timeless elegance of the Captain Swain House, nestled on the prestigious historic William Street in Vineyard Haven. This distinguished Greek Revival main residence and barn-style guest house seamlessly merges historical charm with modern luxury. Step into this meticulously updated 4-bedroom home and you will find a gourmet kitchen with top-of-the-line appliances and custom butcher block island. Attached to the kitchen is a welcoming dining room and wet-bar and a screened porch with garden views. The multiple spacious living areas are flooded with natural light and fireplaces perfect for both entertaining and everyday living. The second floor features 3 beautifully appointed bedrooms with 3 updated tile baths. Additionally, a serene sitting room awaits, complete with built-in bookshelves, creating the perfect place for relaxation or study. Venture to the third level and discover a hidden retreat—a charming bedroom offering privacy distant water views. Outside, there is an expansive yard, a rare find in-town, offering ample space for outdoor gatherings and gardening. The detached 2-story 1-bedroom barn-style guest house beckons, a charming retreat with its own private back deck. From the elegant facade to the landscaped grounds with beautiful perennial gardens, every aspect of this property reflects a rich history and a timeless appeal. The perfect in-town location with easy access to Downtown Vineyard Haven restaurants, shops, beaches and ferry. Excellent rental history.

Unparalleled Chappaquiddick waterfront estate complete with deepwater dock, 300±-foot private beach, private 3-bedroom guest house and garage/barn, plus the unique added opportunity to acquire the private 17±-acre golf course adjacent, also suitable for horses or open space. Designed by award-winning Boston architects Albert-Righter-Tittmann and expertly crafted, this grand yet welcoming home, featured in numerous publications, is a refined modern take on traditional design. Harmonizing with the idyllic coastal scenery, the 5-bedroom main residence captures glorious wide-open views on Nantucket Sound taking in the sunset, legendary yachting regattas and July 4th fireworks. Comfortably styled and beautifully furnished, the inviting light-filled living/entertaining spaces open their doors to the breezy waterside porch. Appointed with classic shiplap paneling, the home also features a gym, sauna and high-efficiency systems. A worlds-away retreat, yet close to Edgartown village.