luxury houses for sale Dukes County, United States

Tucked back from the road on scenic Lake Street, this one-of-a-kind home offers privacy and charm on a beautifully landscaped 0.7 acre lot accented by mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm and inviting atmosphere. The home’s four-level design provides exceptional character and flexibility. The main level features a spacious kitchen with a center island that opens to a dining area. A sunken living room with floor-to-ceiling windows overlooks the surrounding tree canopy, filling the space with natural light. Just off the living room, a large screened porch offers a peaceful setting for relaxing outdoors. Two bedrooms, a full bath, and a laundry room complete this floor. Up the wood staircase, the second level includes a dramatic hallway that overlooks the living area below and leads to a generous primary suite with a spacious bathroom and additional laundry. The third level features a private guest bedroom with its own living area and full bath, ideal for visitors or extended stays. The finished lower level adds even more living space, offering a full bathroom, bedroom windows, and a walkout door to the side yard. A spacious garage provides added convenience and storage. Convenient to the public boat landing on Lake Tashmoo and the Lake Street tennis and pickleball courts, and just a short distance to Downtown, this is the ideal Vineyard Haven location.

Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval, providing exciting possibilities for future expansion. A partially finished walk-out basement adds flexible additional space. Whether enjoyed as a year round residence or seasonal Island retreat, this property offers space, convenience, and potential. To add to this well rounded offering, this property is also being offered turnkey!

Step into a piece of Martha's Vineyard history with this exceptionally charming antique Cape, originally dating back to 1808. While the home proudly retains its authentic historical character, boasting exquisite period details, rich moldings, and wide-pine floorboards, it has been thoughtfully updated to offer the ultimate in contemporary living. There are 5 total bedrooms: 2 on the first floor and 3 on the second floor. Two bedrooms are en suite: 1 on the 1st floor and 1 on the 2nd floor. There are 4 full bathrooms (3 renovated), and a light-filled, spacious kitchen, designed to blend old world charm with modern needs. Additional updates include central AC, 3 lined chimneys, and an upgraded septic system. A bluestone patio is ideal for al fresco dining, and a lovely, professionally maintained backyard and garden complete the storybook picture. Perfectly positioned across from picturesque Owen Park, this property places you at the very heart of Vineyard Haven culture and coastal convenience. Take in water views and boat activity on scenic Vineyard Haven Harbor. Enjoy the newly built town dock and the historic bandstand where you can enjoy the Vineyard Haven Band play on Sunday evenings in the summer. Schedule your tour today and experience the magic of Vineyard Haven living.

Set on a generous 0.3-acre lot in desirable Oak Bluffs, this property offers exceptional potential just moments from Vineyard Sound. A newly installed 6-bedroom septic system opens the door to a variety of expansion opportunities. The home is thoughtfully designed with two separate living areas, ideal for guests or rental possibilities. The main living space features hardwood floors throughout, a spacious living room with a fireplace, kitchen, sunroom, and a primary bedroom with a full bath. An additional shared living room serves as the central gathering space between the two wings of the home, creating a seamless and functional layout. The secondary living area includes a kitchenette, dining space, guest bedroom, and bathroom. The bathroom is currently unfinished, providing the next owner the opportunity to customize it to their taste. Upstairs, the second level boasts high ceilings, abundant natural light, a guest bedroom, and a private office space. Additional highlights include a two-car garage, a large rear deck, and a private backyard setting. An excellent investment or renovation opportunity in Oak Bluffs, offered as-is.

Expanded cottage with in-law suite, garage, and detached studio. On the way to West Chop, it is equidistant to Downtown Vineyard Haven, the flagpole at West Chop, Mink Meadows Golf Club, and Vineyard Haven Yacht Club. This 4 bedroom, 4 bathroom property offers a flexible floor plan, including a private inlaw wing complete with its own entrance, kitchen, living room, full bathroom, and bedroom—perfect for extended family or guests. There are two driveways. The home also features a garage and a finished basement offering excellent storage or future expansion potential. A detached studio at the rear of the property provides wonderful overflow space for a home office, art studio, or guests. The property is only 2/10ths of a mile to the town beach at the end of Grove Ave, and half a mile to the town beach on Owen Little Way. Ready for a new owner's vision and updates, this well-located property presents an exceptional opportunity to enjoy the convenience and charm of this desirable neighborhood. This property is being offered as-is.

Introducing a refined contemporary Chilmark beach house with water views and deeded access to Stonewall Beach on the Atlantic Ocean. The property is set within the storied Stonewall Road and Beach Association - where homes are held for generations and lifelong friendships take root - and offers a true sense of place and continuity. Built by South Mountain Company and thoughtfully renovated and significantly expanded in 2023, the home blends craftsmanship with modern comfort. Enjoy sweeping views of the Atlantic Ocean, Squibnocket Point, and Nomans Land island from both interior living spaces and outdoor vantage points. Designed for multigenerational living, the home offers multiple private zones - including a dedicated media room - allowing for both connection and retreat. This is a rare opportunity to own a meaningful piece of Chilmark—an offering not to be missed.

This enchanting artist-designed property is tucked away on 2.9 private acres in West Tisbury, a thoughtfully composed retreat with pastoral meadows, mature landscaping, and an unmistakable sense of intention and sophisticated taste. The two-bedroom, two-bathroom Main House is complemented by a spacious two-bedroom, one-bathroom Guest Studio with a fireplace, offering a combined 3,771 square feet of living space. A gunite swimming pool, gardens, expansive lawn areas, outdoor shower, and one-car garage complete the setting. Renovated in 2013 and equipped with central air conditioning, the property feels wonderfully secluded while remaining centrally located for convenient access to both up and down Island destinations. Future expansion to 12 bedrooms is possible with a septic upgrade, although the current system meets all regulations. Enjoy effortless access to Lambert’s Cove Beach, 7a Foods, North Tisbury Farm, State Road Restaurant, and all the iconic West Tisbury landmarks.

An iconic retreat in Chilmark, this totally renovated beach house captures sweeping views of the Atlantic Ocean, Stonewall Beach, and Stonewall Pond. The design honors the timeless simplicity of its coastal setting with elegant, understated finishes that allow the extraordinary vistas to take center stage. Designed for effortless indoor-outdoor living, the home's light-filled spaces open to expansive outdoor areas, inviting you to spend your days moving between the comfort of the house and the beauty of the surrounding shoreline. Nearly every room frames breathtaking ocean vistas, creating the feeling of living within a constantly changing work of art. From sunrise over the Atlantic to spectacular sunsets and star-filled skies, every moment here is unforgettable. In the evening, unwind in the hot tub on the courtyard patio, where rising steam meets the night air and the sounds of the ocean provide the perfect backdrop for reflection after a day spent enjoying the sun, surf, and sea. Completing this exceptional offering is a Stonewall Beach lot, providing access to one of Chilmark's most treasured stretches of coastline.

Rare Downtown Vineyard Haven Compound Offering! An exceptional opportunity to own two separate properties being offered together in the heart of Vineyard Haven. Just moments from the ferry terminal, restaurants, shops, and the harbor, this unique package offers the ideal blend of luxury living, investment potential, and an amenity that is nearly impossible to find in town with expansive parking. 33 Lagoon Pond Road is a newly constructed, thoughtfully designed three bedroom, three bathroom home where luxury meets sophisticated coastal charm. Featuring an open floor plan, a designer kitchen with quartz countertops, custom tile bathrooms, and seamless indoor-outdoor living, the home enjoys water views from the living room, bedrooms, and inviting front porch. A private backyard, spacious rear deck, and attached two car garage provide both privacy and convenience, while the property's impressive rental history adds outstanding investment appeal. Complementing the main residence is 29 Lagoon Pond Road, a beautifully renovated two bedroom, one bath cottage offering its own private retreat with a charming rear patio and outdoor shower. Ideal for extended family, guests, employee housing, or additional rental income, the cottage provides flexibility for a variety of ownership opportunities. A true standout feature of this offering is the oversized rear parking lot at 29 Lagoon Pond Road, accommodating approximately ten vehicles. Parking of this scale is exceptionally rare in downtown Vineyard Haven and significantly enhances the property's versatility. Whether you're seeking a family compound, an income producing investment, or a premier in town property with unmatched flexibility, 29 & 33 Lagoon Pond Road represent a truly one of a kind opportunity in downtown Vineyard Haven.

Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to discover a custom circular staircase with dramatic floor to ceiling windows, leading to the upper living area flooded with natural light from the wall of south-facing windows. The living area with high ceilings and woodstove is a comfortable place to congregate, while the kitchen and open dining areas lend themselves to modern day living. Glass sliding doors open onto a spacious 2nd story deck giving the entire living space an intimate relationship with the outdoors. On the first floor there are three total bedrooms; two bedrooms sharing a full bath plus a primary bedroom with a full bath en-suite. Total square footage represents house (1,400 sq. ft.) and guest house (518 sq. ft.). A shared six (6) bedroom septic system services both houses.

A rare opportunity to create a premier in-town compound in one of Edgartown’s most desirable locations. Set on High Street, just moments from downtown Edgartown, this exceptional 16,000+ square foot lot offers tremendous potential to create a substantial five-bedroom residence while enjoying the convenience and charm of village living. The property currently features a 4 bedroom main house, attached 1 bedroom apartment, and an oversized garage with an attached 556-square-foot barn. The property provides a unique foundation for expansion, renovation, or a thoughtfully designed new build. With its generous lot size and coveted location, 49 High Street presents a rare opportunity to create a legacy property within walking distance of Edgartown’s shops, restaurants, harbor, and village amenities.

WATERFRONT WITH DOCK – Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilities are endless. Enjoy water views from virtually every room as the home's spectacular waterfront setting seamlessly extends to your private sandy beach and deep-water dock, offering direct access for boating, swimming, paddle boarding, or simply relaxing by the water's edge. A truly special legacy property offered for the first time in over 50 years where history, charm, and an unparalleled waterfront lifestyle come together.

This Chilmark home is one-of-a-kind - a warm, charming hideaway set on 4.4 spectacular acres just off North Road. At the top of a shady driveway you are met by stone walls so typical of Chilmark from a bygone era. You enter a courtyard through cedar gates where you find beautifully tended flower beds. The porch is the ideal location for you to enjoy the private, peaceful courtyard. Immediately upon entering the home you captivated by the warm ambience. The main living spaces and primary bedroom suite all showcase views of a sweeping meadow punctuated by granite boulders and stately oaks. In addition to the primary bedroom suite and additional sleeping spaces on the main level, there is a large finished lower level with private entrance - ideal for accommodating your guests. Back upstairs and across the courtyard, there is an unfinished structure with screened porch begging to be converted into a bunkhouse, if not a studio or office. There are two garage spaces for cars or boats. Visitors are encouraged to walk the grounds and enjoy the private nooks and crannies of this magical piece of land. The property is less than 2 miles to Menemsha Village and Beach, 1 mile to the north shore beach at Great Rock Bight, and a 3-mile drive to parking at Lucy Vincent Beach.

3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset your mortgage. The main house features a stunning solarium or sunroom, a cheerful efficient kitchen, and a sweet living room anchored by a beautiful stone fireplace. The main house has been emptied out and awaits the new owner's touch (please refer to images showing digital staging). Both the main house and the apartment have been freshly painted throughout, radiating a clean and bright atmosphere. Situated on a spacious lot, the site is large enough to support a 4-bedroom septic system; a design is currently being finalized by Sourati Engineering (buyer to be financially responsible for the upgrade). Other features include oak floors, two decks for outdoor enjoyment, a vintage garden shed, and a full dry basement for additional storage.

Nestled at 5 Pinetree Lane, Vineyard Haven, MA, this single-family residence in Dukes County presents a unique opportunity to own a piece of classic American architecture. Built in 1927, this home offers a blend of vintage charm and comfortable living. The residence features three full bathrooms, providing convenience and privacy for all occupants. Imagine mornings where everyone can prepare for the day without the rush, and evenings where relaxation is never compromised. The thoughtful design ensures that personal space is always readily available. With four bedrooms, this home provides ample space for rest and rejuvenation. Envision each room becoming a personalized sanctuary, tailored to individual preferences and needs. Whether it's a tranquil space for sleep, a vibrant area for hobbies, or a practical room for remote work, these bedrooms offer the flexibility to adapt to any lifestyle. The 2730 square feet of living area unfolds to provide a comfortable and inviting environment.

Introducing a landmark property in Edgartown’s Starbuck Neck enclave, just one tenth of a mile to Fuller Street Beach. Included in this sale is an adjoining vacant buildable lot. 14 STARBUCK NECK features a 7-bedroom house with 5 full bathrooms, garage, and plunge pool. Known as the Tower House, this home offers delightful views of the harbor from the first and second floors. The views from the bedroom and office located in the tower are stunning. 23 THAYER STREET is an extremely rare vacant lot in the heart of the Starbuck Neck neighborhood. With well over a third of an acre of land, the lot will comfortably accommodate a 5-bedroom house with guesthouse and pool.

Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home for a client list that included Lady Diana Spencer. The historic main house has been completely modernized. There are 6 bedrooms spread out over almost 6000 square feet, a detached pool house, swimming pool, and Har-Tru tennis court. Wherever you are in this gracious home you will be blessed with sweeping views of the open fields, stone walls, and horses in the neighboring farm, a scene as if from a painting done in a previous century. Included within the 10 acres is a separate 3.3-acre parcel of land that will accommodate a full-size home. The property is part of the Tashmoo Farm Association which includes deeded access to the association dock on Lake Tashmoo and tennis courts.

Downtown Vineyard Haven with Harbor Views. Positioned between the energy of Main Street and the quiet prestige of West Chop, the location delivers a rare balance of downtown access, privacy, and harbor frontage. Built in 2015, the three-bedroom, two-bath modern ranch is designed for easy first-floor living with expansive water views. Wide, harbor-facing windows showcase the meadow and water beyond. Mornings start with sunrise over the water, while evenings slow as the light fades across the shoreline. The interior feels open, calm, and intentional, with spaces that flow naturally toward the outdoors and keep the focus where it belongs. Outside, the landscape opens gently toward the water. A private beach path sits immediately adjacent to the Vineyard Haven Yacht Club, offering sailing, tennis, dock access, and a café just steps away—an uncommon amenity pairing in such a peaceful, natural setting. Whether enjoyed as a personal escape or leveraged as an income-producing property, the home’s strong rental history reflects its wide appeal. A rare opportunity to own directly on Vineyard Haven Harbor, with a mooring available and the best of Martha’s Vineyard right outside your door.

This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for entertaining. The design is casual but practical, evidenced by the well-appointed kitchen which offers direct access to the rear deck for an eat-in or eat-out option. With separate finished living quarters on the garden level, the home easily accommodates guests, or multi-generational living. The expansive deck invites morning coffee, summer gatherings, and peaceful evenings surrounded by nature. Mature plantings bloom on stone-scaped retaining walls and evergreen trees provide ultimate privacy. You are just moments from the harbor, shops, and ferry, and yet this property also offers seclusion and privacy - this is a rare combination in this price point.

Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort. Inside, a thoughtfully designed floor plan welcomes you with generous living spaces. At the heart of the home is a chef’s kitchen featuring custom cabinetry, high-end appliances, and stylish finishes—perfect for both everyday living and entertaining. The open-concept living and dining areas flow seamlessly, enhanced by updated systems and central air conditioning for year-round comfort. Upstairs, the primary suite provides a serene escape with a spa-like tile bath and soaking tub. Two additional guest bedrooms share a beautifully appointed full bath that also includes convenient laundry. Unique details like a compass rose stained glass window add a distinctive nautical touch. The finished lower level offers even more living space, including a large bedroom—ideal for guests or extended family. Outdoors, a stunning mahogany deck overlooks the newly landscaped backyard, complete with an outdoor shower and perfect areas for entertaining. With close proximity to downtown Vineyard Haven and the beaches of Vineyard Sound, this exceptional home captures the essence of island living—timeless, refined, and move-in ready.

Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower, perfect after a day at the beach. Also on this level is a comfortable guest bedroom with peaks of the harbor, a stylish full tile bath with a glass-enclosed shower, a cozy living area, and washer/dryer for convenience. Upstairs, cathedral ceilings and a gas fireplace create an inviting open-concept living space. The gourmet kitchen is outfitted with sleek Bosch appliances, a large center island ideal for entertaining, and an adjoining dining area. Enjoy panoramic water views of the harbor, passing ferry boats, and Vineyard Sound from the entire second floor, or step out onto your private deck, perfect for alfresco dining or morning coffee. Just steps from your door, a private path leads to the association’s sandy harbor beach where you can store your kayak or launch your boat. This condo also includes a dedicated parking space and an enclosed storage area under the house ideal for bikes, beach gear, or seasonal items. With easy access to downtown shops, restaurants, ferry terminal, and local beaches, this condo offers the ultimate combination of luxury, convenience, and island charm. A rare opportunity for carefree coastal living on Martha’s Vineyard.

Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a detached garage, and exclusive access to Hidden Cove's sought-after amenities, including a private boat launch. Just minutes from Oak Bluffs, Farm Neck Golf Club, beaches, and the bike path, this is a place where generations return to create the kind of Martha's Vineyard summers that never go out of style.

Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone bench, offering stunning water views of Vineyard Sound and the Elizabeth Islands. Ideally located just steps from Gray's Beach and dock, this is one of the most picturesque properties in Seven Gates Farm. The Seven Gates Farm community consists of 45 homesites on 1,600 acres with 1,000 acres of protected conservation land, open fields, woodlands, ponds, and miles of trails for walking and horseback riding. Residents of Seven Gates Farm also enjoy exclusive access to 1.5 miles of private beach, two piers, and two tennis courts. This rare opportunity allows you to become part of a remarkable community, once an assembly of farms, that remains dedicated to the preservation and stewardship of the land.

Set high on the north shore with panoramic waterviews of Vineyard Sound and deeded private beach access, this secluded 9.8-acre property occupies a rare setting bordered by conservation land and the Menemsha Hills trail network. The spacious, meticulously maintained residence features a reverse floor plan that accentuates the natural light, soaring ceilings, and breathtaking views. The upper level includes an open-concept kitchen, dining, and living area, along with a private primary suite and dedicated office space. There is a large open deck and a screened porch o n this level, as well as a deck off the primary bedroom suite. Thoughtfully designed for both everyday living and entertaining, the home includes amenities such as air conditioning, a whole-house generator, an integrated sound system, outdoor lighting, and more. Outside, the grounds are equally impressive, featuring a tennis court, landscaped gardens with a water feature, and a large open meadow spanning several acres, all surrounded by mature woodland for exceptional privacy. No neighboring homes are visible from the property. There is ample room to add a swimming pool, and the parcel may offer subdivision opportunities. Ownership also includes rights to Brickyard Beach.

A rare offering on the shores of Menemsha Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Thoughtfully designed with striking modern architecture, walls of glass, and seamless indoor-outdoor living, this one-of-a-kind compound captures breathtaking water views from nearly every room. Set on 4.9 acres with a private 115-foot deep-water dock, the property represents an irreplaceable opportunity, as a waterfront estate of this scale and caliber could no longer be replicated today. The main residence features six luxurious ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired bathrooms. Two state-of-the-art kitchens appointed with top-tier appliances provide exceptional spaces for entertaining, while the dramatic main living area showcases soaring cathedral ceilings and panoramic pond views. A screened porch and expansive waterfront deck create effortless transitions between interior and exterior living spaces. Upstairs, a striking glass-lined hallway with a dramatic glass floor overlooks the water, leading to guest suites with private baths and access to a second-floor deck. Exceptional amenities include a private theater with massage seating, wine cellar, outdoor shower, and a hilltop writer’s cottage with sweeping waterviews. Set just beyond the main house is the pool house. The pool house is a private wellness retreat featuring a heated indoor pool, spa, sauna, cold plunge, steam room, wet bar, and spacious enclosed porch surrounded by retractable glass doors. The second floor includes a full guest suite with a bedroom, living room, laundry, and dual balconies overlooking Menemsha pond. The estate also includes an impressive 1,927 sq. ft. barn-style entertainment pavilion designed to complement the property’s contemporary aesthetic while offering exceptional recreational amenities. The upper level features a professionally designed fitness center with floor-to-ceiling windows overlooking the grounds and pond, alongside a sprawling recreation lounge with space for indoor basketball, billiards, ping pong, and additional sporting activities. Below, the structure houses an expansive six-car garage, ideal for luxury vehicle storage, boating equipment, and recreational gear. Completing this incomparable estate are a private tennis court and charming boathouse by the dock for paddleboards and waterfront equipment. An unparalleled modern retreat in one of Martha’s Vineyard’s most exclusive waterfront settings.