Historic Water View Elegance Meets Modern Luxury in Vineyard Haven: 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. There are 2 en suite bedrooms, 1 on the first floor and 1 on the second floor. In addition, there are 4 full bathrooms (3 newly renovated), and a light-filled, spacious kitchen, designed to blend old world charm with modern needs. Additional updates include central air conditioning, 3 lined chimneys, and an upgraded septic system. A bluestone patio is ideal for al fresco dining and summer barbecues. And a lovely, professionally maintained backyard and garden complete the storybook picture. Perfectly positioned right 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 the boat activity of scenic Vineyard Haven Harbor. Enjoy front-row access to Owen Park with the newly built town dock and the historic bandstand where you can enjoy the Vineyard Haven Band play Sunday evenings in the summer. When you want to explore further, you are a short walk from the village where there are several exciting new restaurants, a multitude of shops, and the historic Playhouse. Whether you are looking for a gracious year-round island residence, a seasonal getaway, or a desirable vacation rental income producer, this historic gem delivers on every front. Schedule your private tour today and experience the magic of Vineyard Haven living. Offer mostly furnished and equipped with some exclusions.

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For the very first time, the historic Ben Luce Homestead (circa 1850) is being offered on the open market. This charming farmhouse blends rich Island history with timeless appeal. Once home to Benjamin Norton Luce (1840–1912) — Civil War veteran, blacksmith, and town constable — the property sits on 1.5 acres of pastoral land and offers 5 bedrooms, 2 full baths, solar panels, barn, and a newly updated septic system meeting current standards. Thoughtfully restored for year-round living, the home provides comfort, character, and sustainability. Just minutes from Vineyard Haven’s harbor, shops, and ferry, this rare offering combines privacy with exceptional convenience.Whether enjoyed as-is or further restored as a preservation project, the Ben Luce Homestead is ready for its next chapter — as a year-round residence, summer retreat, or historic Island treasure. The barn offers the perfect foundation for adding an ADU or additional living space, enhancing both functionality and value.

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Ideally located just minutes from the heart of Vineyard Haven, 21 Davis Street offers exceptional island living in this beautifully crafted five-bedroom, four-bathroom home encompassing 3,704 square feet of thoughtfully designed living space. Rich hardwood flooring, custom cabinetry, elegant Restoration Hardware vanities, and custom tilework throughout the bathrooms reflect exceptional quality and craftsmanship at every turn. The grounds are equally impressive, featuring beautiful stonework, handcrafted bluestone patios, and professionally landscaped outdoor spaces designed for effortless entertaining. Spend summer evenings by the outdoor fireplace, unwind in the Jacuzzi, or rinse off after the beach in the private outdoor shower, all part of the quintessential Vineyard lifestyle. Lovingly maintained and thoughtfully designed, this home offers an exceptional blend of comfort, style, and convenience just moments from Vineyard Haven Harbor, the ferry, shops, restaurants, and the Island's renowned beaches.

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Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District and just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. The property also has potential for an additional buildable lot. For 35 years, home of Susan Branch, the illustrious self-taught illustrator and author of New York Times best-seller "Martha's Vineyard, Isle of Dreams," this quintessential Greek Revival gem with Neoclassical touches enjoys over 3,468 s.f. of indoor space including the summer kitchen (now pantry/laundry) on more than a half acre in town with wood floors throughout and cheerful eastern sunlight mornings and western afternoon sunlight with evening skies. With period paneling, crown molding, and 9' ceilings, the floor plan includes front hall entry with lovely curved staircase, front parlor-studio, formal living room with fireplace and bay window, spacious dining room, second side entrance vestibule used as a dry bar, cozy wood paneled study/tv room ~ "the Snug", eat-in kitchen with wainscotting, east-facing side porch, laundry/pantry/storage room, and a half bath. With a convenient back staircase off the kitchen, the second floor with 8.5" ceilings includes additional spacious rooms: A large primary bedroom with fireplace and ensuite bath, sitting room, linen closet, three additional bedrooms, one with bay window, plus two additional full baths ~ one with claw foot tub. Wonderful two-story carriage house - barn, expansive lawn and yard, tea-house pergola for afternoon tea, cocktail social, and alfresco dining. Seller has drawings for potential renovation of the barn to include a studio apartment - see Documents. Mature plantings including privet, flowering trees and bushes, perennials, historic Linden trees, and herb garden. Six bedroom approved Title 5 septic. A rare opportunity for those who appreciate the history and value of historic homes in a sailing port which as been described as "the sweetest little harbor on the east coast." This property and the owner's abutting Town Approved Building Lot comprised of 12,527 s.f on William Street is available for purchase together for $3,200,000. Some furnishings available for purchase by separate bill of sale.

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Nestled on an acre of beautifully landscaped grounds in a tranquil, park-like setting, this home is tucked away on a quiet lane within an established neighborhood. Located just a quarter mile from miles of Land Bank walking trails and less than two miles from Main Street, it offers the perfect opportunity to embrace the Vineyard lifestyle, just minutes from the vibrant center of Vineyard Haven. Thoughtfully designed for both everyday living and entertaining, the main level boasts hardwood floors, high ceilings, and lots of windows that bathe the living areas and bedrooms in natural light. The kitchen serves as the heart of the home, featuring a center island and a dining area that opens onto a deck and attached gazebo—ideal for outdoor dining and gatherings. The inviting living room, complete with a propane fireplace, provides a warm and welcoming space. Three bedrooms—including a primary with ample closet space and a newly refinished bath are all located on the first floor. Additional highlights include new stainless-steel appliances, a Bertazzoni range, Andersen windows, renovated baths, fresh paint, refinished floors, custom window treatments, plantation shutters, and a generator. This turnkey property is ready for immediate occupancy, allowing you to settle in and enjoy from day one. On the garden level, you'll find versatile space for additional living, relaxation, or exercise. The family room includes a half-bath and sliders that open to the patio and outdoor shower. A separate guest suite complete with bedroom, den, full bath, and kitchenette provides flexible accommodations for visitors. Meticulously maintained inside and out, this home is ready to welcome its next owner.

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Welcome to this meticulously maintained home which features an attractive open kitchen with an island that seats four. The kitchen has a wall of built in appliances and a walk-in pantry for ease of cooking. The kitchen flows into the open dining area and lounge area with a wall of sliding glass doors that lead to the large outdoor entertaining area which features a lounge area and two eating areas, all overlooking the expansive manicured lawn. On the 1st floor is a full bath and a bedroom that is currently being used as a sewing room. The top floor showcases the expansive primary bedroom en-suite which has a seating area with sliders that lead to a private outdoor balcony. This bedroom offers a large walk in closet and a luxurious bathroom. On the lower level there are two more guest bedrooms, a full bath, a lounge and a home office. This property is complimented by its attached garage and outdoor shower. There is a six bedroom septic system in place.The plot can support a guest house with proper approvals from the HOA and the town. The property is truly turn-key and has been meticulously maintained. A true gem!

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Tucked away in a private, beautifully landscaped setting, this charming Vineyard farmhouse offers a wonderful blend of privacy, space, and in-town convenience. Just moments from town, the ferry, and shopping, the four-bedroom, three-bath home sits on a spacious 30,000-square-foot lot with a five-bedroom septic system. Inside, sun-filled spaces, warm wood floors, built-ins, and a welcoming layout create an easy, comfortable feel. The first floor includes a private bedroom with en suite bath, while upstairs offers three additional bedrooms, two full baths, and laundry. The spacious living room opens to an enormous screened porch and back deck overlooking the beautifully landscaped yard—perfect for morning coffee, summer gatherings, and long Vineyard evenings. A truly special place to make lasting memories.

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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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Welcome to 18 Sylvan Avenue, a delightful, custom-crafted four-bedroom, four-bath, contemporary-style home set at the end of a quiet neighborhood road in Vineyard Haven. Surrounded by eight acres of conservation land, the property offers a peaceful setting with a spacious wraparound deck overlooking the natural landscape. It truly feels like its own private enclave, both inside and out. The home is in pristine, move-in-ready condition and has been thoughtfully renovated and meticulously maintained by the current owners. A welcoming entry leads directly into the open-concept space where a well appointed living room with fireplace flows into the dining area and kitchen. Positioned to the right of the entry is the primary bedroom suite, while two additional bedrooms and two bathrooms are tucked beyond the kitchen on the opposite side of the home, creating a functional and well designed layout which maximizes privacy. A finished lower level with a full bathroom and laundry provides additional flexible living space or a fourth bedroom. Skylights and sliders throughout the home fill the interior with natural light and create an easy connection to the multiple decks, beautiful mature gardens and woodlands. With an impressive rental history, this unique property is offered turnkey, making it an ideal opportunity as a year-round residence, Island retreat, or investment property. A true gem, conveniently located only 1.5 miles to Vineyard Haven’s Main Street shops, restaurants and ferry terminal, and only 5 miles to all that downtown Oak Bluffs has to offer!

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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, including in-law suite, 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. Same day and short notice showings now available!

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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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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 of a 4-bedroom NitROE septic system, as required by the Town of Tisbury.

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