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$1,450,000
4 Beds ⋅ 3 Baths ⋅ 73551628 MLS
Charming Property in the Heart of Vineyard Haven. A rare opportunity to own a beautifully maintained main house and guest house nestled on a generous 25,100 square foot lot in Tisbury. This special offering combines charm, privacy and versatility, surrounded by a stunningly landscaped yard. The main house has three full bedrooms and two full bathrooms. The one-bedroom and one-bathroom guest house has a kitchen, loft, private deck, and outside shower. Enjoy easy access to the town's vibrant waterfront, boutique shops, local restaurants, cafés, galleries, and the ferry terminal, making it an ideal location for both year-round living and seasonal escapes. Per the Board of Health, there is no land area restriction; therefore, if a new septic system can be installed without variances, the approved bedroom capacity may be increased.The main house and the guest house each have their own basements. Each basement has a washer and dryer and lots of room for storage.

21 W Spring St, Tisbury
$2,325,000
4 Beds ⋅ 4 Baths ⋅ 73549701 MLS
COASTAL CHIC RETREAT IN VINEYARD HAVEN. Located less than five blocks from Main Street in Vineyard Haven, this classically styled home is perfectly positioned for easy access to restaurants, shops, the harbor, and the ferry, offering the ideal blend of in-town convenience, relaxed island living, and timeless Vineyard appeal. The open-designed living area flows seamlessly to the outdoor living spaces, creating an effortless connection between indoors and out. A wraparound porch, bluestone patio, patio areas, and firepit create multiple spaces for al fresco dining, entertaining, and gathering after a day at the beach or on the harbor. There is also possible pool potential, adding another layer of future enjoyment. Inside, the home features a cook’s kitchen with granite countertops and stainless steel appliances, beautiful hardwood floors throughout, and four bedrooms, each with its own en suite bathroom. Offered furnished, the property is ready for immediate enjoyment and has an establis

54 Amelia's Crossing, Tisbury
$1,365,000
2 Beds ⋅ 3 Baths ⋅ 73543902 MLS
Discover the charm of Vineyard Haven in this delightful two-bedroom, 3 bath cottage, ideally located just moments from downtown, the Steamship Authority, and the picturesque Lagoon. Whether you're looking for a year-round residence, vacation retreat, or investment property, this home offers the perfect blend of comfort and convenience. Inside you'll find a bright and welcoming floor plan with spacious living areas, two well-appointed bedrooms and two full baths with a full bath downstairs. Close to town, marina, shopping, restaurants, and beaches.

51 Davis St, Tisbury
$1,790,000
3 Beds ⋅ 3 Baths ⋅ 73536989 MLS
Included in the asking price are two separate parcels: a beautifully updated 3-bedroom home and an adjacent 16,000 square foot buildable lot. No subdivision is required. The lot is ready to build on immediately or may be sold separately after closing, offering exceptional flexibility for a family compound, second home, or investment. An easement is being established along the existing driveway to provide access to the residence while allowing the buildable lot to remain an independent parcel.Situated just moments from downtown Vineyard Haven, the ferry terminal, shops, restaurants, and harbor, the beautifully maintained home offers over 2,300 square feet with 3 bedrooms, 2.5 baths, central air, an updated kitchen with walk-in pantry, and a substantial 2010 addition featuring a spacious living room and second-floor primary suite. A detached studio, landscaped grounds, large deck, and full walk-out basement complete this rare Vineyard Haven offering.

41 & 0 Cook Street, Tisbury
$2,695,000
5 Beds ⋅ 2 Baths ⋅ 73441105 MLS
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.

187 Lagoon Pond Road, Tisbury

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