Thoughtfully designed with custom features throughout, this in-town Vineyard Haven home is the perfect blend of coastal charm and modern sophistication. The 4 bedroom 3 bath property offers a comfortable, easy flowing layout with gleaming hardwood floors and open sun-filled spaces. At the heart of the home is a chef-inspired gourmet kitchen with premium appliances, ample counter space, a generous walk-in pantry and a separate window-lined dining area ideal for both casual or formal dining. Enjoy alfresco dinners on the private deck or unwind on the cozy porch, creating the perfect backdrop for island evenings. Located steps from the ferry, shops, restaurants, and the Vineyard Haven Yacht Club, you’ll have everything at your fingertips while still enjoying a peaceful, private setting. Perfect as a year-round residence or island retreat, this exceptional Vineyard Haven home offers a rare opportunity to enjoy the best of Martha’s Vineyard living.

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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.

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Ideally located at the beginning of Hines Point, this light-filled, well-maintained home offers a central setting with easy access to the Lagoon, the MV Museum, and town. Public water access is just a short walk away, making it easy to enjoy all the benefits of this special area. Set on a gentle rise overlooking the Lagoon, the home is filled with natural light and offers beautiful water views. A bright sitting room welcomes you and flows easily into the kitchen and dining area. The dining room opens to a large deck, perfect for outdoor dining or simply enjoying the view. The cathedral living room is filled with glass and natural light, with a fireplace and sliders to the deck that create an easy indoor outdoor feel. The first floor includes a bedroom with a slider to a private deck and a renovated full bath, ideal for one level living. Upstairs are two comfortable bedrooms connected by a Jack and Jill bath. The grounds are just as inviting, with a park like yard, mature trees, and thoughtful landscaping that provide both beauty and privacy. An irrigation system keeps everything lush, while the pea stone driveway lined with cobblestones adds classic Vineyard charm. The home is equipped with a solar array and heat pumps for efficient, year-round comfort. An easy, comfortable home in a prime location with great light, views, and a setting that feels both private and connected to everything. Seller will provide design, permitting and installation of a 4-bedroom NitROE septic system, as required by the Town of Tisbury.

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Ideally situated on Main Street in Vineyard Haven, just moments from the Yacht Club and West Chop, this charming four-bedroom, six-bathroom home offers the perfect blend of convenience, comfort, and Island living. Set on a quarter-acre lot, the property features a private and inviting backyard—ideal for entertaining, gardening, or simply enjoying warm summer evenings. Inside, generous living spaces and a flexible floor plan provide plenty of room for family and guests alike. Enjoy the rare combination of a peaceful residential setting with the convenience of being just a short walk to downtown Vineyard Haven’s shops, restaurants, ferry terminal, and harbor. Whether you’re seeking a year-round residence, seasonal retreat, or investment opportunity, this well-located home captures the best of Martha’s Vineyard living. A wonderful opportunity to own a home in one of Vineyard Haven’s most desirable neighborhoods, where town, beaches, and West Chop are all at your doorstep.

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1/2 acre of commercial land in the State Road B-2 district. Possibilities are endless for the right business. Also available, next door, is a commercial building that currently has 10 rental units. $6,000,000.

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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.

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Ideally situated just minutes from the ferry, downtown Vineyard Haven, and West Tisbury, this charming, meticulously maintained property offers exceptional flexibility for year-round living, seasonal escape, or income potential. The main residence features three bedrooms and an inviting open-concept floor plan, seamlessly connecting an updated kitchen, living room, and dining area, perfect for entertaining or relaxed island living. Expansive decks extend the living space outdoors, overlooking mature plantings and beautifully established garden areas throughout the property. The home is powered by an owned 5kw solar panel system serving the entire property, offering energy efficiency and reduced utility costs. Agent has a list of detailed upgrades upon request. Adding remarkable versatility, a 900 square foot barn style studio offers space for a home office, artist's studio, workshop, or creative retreat, while a private two bedroom garden apartment, complete with its own separate entrance, provides excellent rental income potential or comfortable accommodations for extended family and guests. Ample parking and move-in ready condition round out this rare combination of location, character, and income producing flexibility on Martha's Vineyard. Please note: the property is located within the Vineyard Haven watershed, and a new or upgraded nitrogen-mitigating septic system will be required.

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Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtfully designed 3-bedroom, 3-bathroom home offers modern downtown living just steps away from the ferry terminal, restaurants, shops and all that Vineyard Haven has to offer. Where luxury meets sophisticated coastal charm complete with an open floor plan, luxury kitchen featuring quartz countertops, custom tile bathrooms and seamless living both indoors and out. Enjoy water views from the living room, bedrooms and the inviting front porch, perfect for relaxing or entertaining, while the private backyard and spacious back deck provide the privacy many desire. The two-car garage provides a rare in-town convenience, for both parking and storage of your island car and beach gear. The property also boasts impressive rental history, look no further for your next in town purchase - an exceptional, well-rounded offering! Note: This property is also available for purchase with 29 Lagoon Pond Road as a combined offering for $3,295,000.

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Close to town with exceptional indoor / outdoor flow & privacy. Consider this beautifully designed home just minutes from town. The first floor features a bright, open kitchen + dining area flowing into a welcoming living room with a fireplace. From there, step onto a spacious deck—ideal for al fresco dining and lounging—complete with direct access to a hot tub and nearby outdoor shower. The main floor primary suite is a true retreat, with lofty ceilings, a large walk-in closet, and an elegant bathroom with soaking tub. Doors open to a screened porch that feels like a private sitting room—and connects you easily to the outdoor amenities like the hot tub and outdoor shower. Hardwood flooring spans the first floor, with a convenient half bath for guests. Upstairs, find two light-filled bedrooms with generous closets, eave storage, and a full bath, and cozy cork flooring underfoot. The walk out basement is primarily finished into a flexible space with great natural light. This is ideal for a gym, office, or casual living room. There is ample dry storage and potential to use it as a fourth bedroom (septic permitting). Additional Highlights: The level of landscape and hardscape on this property really elevates the setting. The yard is spacious and well-fenced. You can walk past an upper patio area to a private gate where you can jump on trails for a nice walk from your backyard. The sunny front covered porch has ample room for outdoor living and enjoying the south side of the property. The mature plantings really create a feeling of privacy on this serene lot with the Vineyard Haven amenities so close by (restaurants, Mink Meadows conveniently located behind the house, the VH Yacht Club, West Chop Yacht Club, Owen Park, Tashmoo, and the town tennis courts -clay and hard surface). Life is convenient in Tisbury! Don’t miss this opportunity to live where design, comfort, and location converge. An existing five-bedroom septic system allows for easy expansion of an additional lower-level bedroom and bath, as well as an ADU.

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Rarely does such a unique, waterfront location become available. With amazing, 180+ degree views of the lagoon from one side of the property, and the Vineyard Haven Harbor on the north side of the property. Wake up to glorious sunrises. Be entertained by a variety of waterfowl throughout the seasons. Have your vessel at the ready right off the shore. The moment you walk onto the property, the tranquil feel and the cooling shade trees will make you forget that you are still so close to town and ferry. The property is hugged by the Lagoon on one side and Vineyard Haven Harbor across the street on the other. Elevated above Beach Road and the lagoon, there are 2 structures on the property. The first, sited on the lagoon with private water access, is a year-round home with breathtaking, expansive views up and across the lagoon. The upper level has a spacious deck overlooking the gardens and sweeping views of the lagoon. The waterside patio has beautiful perennial gardens. A canopy of mature shade trees keeps the property cool. Enjoy meals al fresco in the shade while enjoying the water views. There are many creative details throughout. The sellers have been actively making improvements to increase the commercial usage. Soon the be an art gallery, the commercial building is currently used as an artist’s studio. Built with SIPS construction, this building is energy efficient and wind resistant. Property is connected to the town sewer and town water. Please note: This property is being sold "as is". Buyer is responsible for completing the necessary due diligence with the town and an engineer about this unique property that offers a plethora of opportunities.

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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."

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This 1.1-acre waterfront lot is located at the end of a quiet lane abutting 20+ acres of conservation land. The level and heavily wooded lot sits high on a bluff overlooking the Lagoon. The lot has been engineered, and the bounds have been staked. A buyer would be able to connect to Town water nearby, and an enhanced septic system should allow at least four bedrooms. This quiet, beautiful neighborhood has seen many improvements and new construction in recent years, making it quite desirable. While being a tranquil neighborhood, you are still in close proximity to the shops and restaurants of Main Street, the Steamship Authority, Museum, and the MV Film Center.

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