A rare opportunity, this Hines Point waterfront compound offers expansive views of the Lagoon and 100 feet of private beach. The home was built and has been enjoyed by the same family for gathering and summer recreation over generations. The main house offers an open first floor layout with high ceilings and large windows facing the water where you can watch sunrise over the water. A first floor bedroom and bath, expansive living and dining area, and an updated kitchen make up the first floor. There's also an inviting sunroom and large deck perfect for morning coffee or evening cocktails while watching the boats on the Lagoon. The second floor offers a large primary bedroom with en-suite bath and private balcony as well as a second guest bedroom. The bright walk-out finished basement has a family room, full bath, a bonus room, and additional storage space. The property also features a two-car garage and a charming boathouse at the edge of the sloping lawn. The beach is generous and sandy; inviting picnics, swimming, fishing and clamming or you can launch your kayak or paddleboard right from your backyard. The property has a mooring - available to a new owner with proper permitting. The calm Lagoon, which opens to the Vineyard Haven Harbor, is made for boating. The iconic Hines Point neighborhood is a short stroll to Tisbury town center with shops and dining and The Vineyard Haven Yacht Club.

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Perched high above Lagoon Pond, this exceptional Martha's Vineyard estate offers a rare convergence of natural beauty, refined comfort, and Island living at its best. Set on 2.25 secluded acres, spectacular panoramic views stretch across the shimmering waters of Lagoon Pond, a private haven for kayaking, sailing, and peaceful exploration. The thoughtfully designed interior features four bedrooms and three full bathrooms, with generous windows framing breathtaking water views from nearly every room. A large family room/library, additional formal living room, and a private guest suite set apart on the far side of the residence offer ample space for homeowners and guests. Outside, the lawn sweeps to the water's edge, where a sandy shoreline invites you to launch a kayak, cast a line, or linger over a sunset picnic. Direct water access puts boating and paddling within easy reach. A detached three-car garage with a finished room above provides generous storage for watercraft, paddleboards, and all the trappings of Island adventure. Just minutes from the shops, restaurants, and harbor are worlds away in feeling, yet close to the best of the Island. Note: Septic Passed Title V inspection, but buyer will need an enhanced de-nitrification septic system Per town of Tisbury regulations. Expansion to six bedrooms possible.

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Set privately in one of Vineyard Haven’s most tranquil enclaves, 30 Water Gate Road is a rare legacy offering defined by pastoral beauty and ready access to Lake Tashmoo. The nearly 5,000-square-foot residence offers five bedrooms and generous living spaces designed for both gathering and quiet retreat, with an effortless indoor-outdoor flow that embraces the surrounding landscape. Bedrooms are thoughtfully positioned on opposite wings of the home, with three on one side and two—along with a striking office—on the other. The primary suite is exceptionally private, overlooking neighboring lawns, gardens, and the conservation land. The main living room is warm and inviting, anchored by a massive wood-burning fireplace and complemented by beautiful hardwood floors. A chef’s kitchen connects seamlessly to both indoor and outdoor living areas, ideal for entertaining. An attached two-car garage adds convenience. The grounds feature a wide-open lawn bordered by a classic stone wall, mature plantings, and established garden beds, including a fenced vegetable garden. A post-and-beam barn/boathouse offers flexible space for storage, recreation, or workshop use. Ownership includes access to neighborhood tennis courts and a dock on Lake Tashmoo, making it easy to enjoy morning paddles, sunset swims, and the best of Vineyard coastal living. A property of this scale, setting, and heritage rarely comes to market—an opportunity to carry forward a truly special family estate that combines an "up-island" feel with the convenience of nearby shops and restaurants.

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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.

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NOW INCLUDING RARE 12,527 S.F. TOWN APPROVED BUILDING LOT ON WILLIAM STREET! 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, just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. 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 room, on .92 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 a welcoming front hall entry with lovely curved staircase, front parlor, 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 includes additional spacious rooms with 8.5' ceilings: A large primary bedroom with fireplace, double closets and ensuite bath, sitting room, linen closet, three additional bedrooms, two with double closets, 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 (6) 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." Some furnishings available for purchase by separate bill of sale. This property is also available for purchase for $2,300,000 without the approved 12,527 s.f. buildable fronting on William Street.

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HINES POINT WATERFRONT GEM with 85 feet of frontage on the Lagoon, offering ever-changing water views and the perfect vantage point to watch the Steamship Authority ferries arrive in Vineyard Haven Harbor. Enjoy the charming, timeless cottage with a one-car garage as an idyllic summer retreat, or bring your Vineyard vision to life with beautiful architectural plans by Sullivan + Associates Architects. Perched atop a gentle embankment, this exceptional property captures expansive views of the Lagoon, harbor, and town. A private staircase leads to the water's edge, where you can launch a kayak, paddleboard, or small boat and explore the Lagoon and beyond. Just a short stroll to the Martha's Vineyard Museum, downtown Vineyard Haven, shops, restaurants, and the ferry, this is a rare opportunity to own in one of the Island's most coveted waterfront locations.

NEW

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Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. This five-bedroom, four-bath residence combines historic character with modern comforts. The home features a gracious living room, dining room, office, and an inviting kitchen/breakfast room. There are five original fireplaces, and 3 zone central heat and AC. Additional conveniences include a mudroom, laundry room and a large screened porch where you’ll find yourself spending more time than anywhere else in the summer time. Two of the five bedrooms are on the first floor, including a private ensuite with a full bath. The home is notable for its unusually large and abundant windows, flooding the south-facing interior with natural light. The winding staircase is a sculptural centerpiece that greets you as you enter through the original front door. Renovations include a new roof over the porch, three modernized bathrooms, and updates throughout the first and second floors, all carefully designed to honor the home’s historic charm. Outside you will find a lawn area and back yard patio that overlook perennial plantings including roses, hydrangeas and dogwood and a white picket fence that creates nice privacy. Plus there is off-street parking for 2 cars. Located just one block from Main Street and two blocks from the Vineyard Haven ferry terminal , this prime location offers easy access to shopping and restaurants and the Tisbury Elementary School. The town tennis courts are just a half-block away, and its a leisurely stroll to the town beach at Owen Park. This is a rare opportunity to own a piece of Vineyard Haven history, where timeless charm meets contemporary comfort.

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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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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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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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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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