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$3,100,000
3 Beds ⋅ 1 Baths ⋅ 73564072 MLS
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, paddle board, 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.

36 Hines Point Rd, Tisbury

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Donnelly + Co..
$1,285,000
3 Beds ⋅ 3 Baths ⋅ 73559180 MLS
Just moments from downtown Vineyard Haven, the ferry terminal, shops, restaurants, and harbor, this beautifully maintained three-bedroom home combines distinctive character with thoughtfully updated spaces, modern comforts, and a peaceful residential setting. The home offers over 2,300 square feet of living space with three bedrooms, 2.5 baths, central air, and wood flooring throughout. An updated custom kitchen by French Accent, with a walk-in pantry, opens to the dining area, while a first-floor powder room with laundry adds everyday convenience. A substantial 2010 addition expanded the home with a spacious, light-filled living room and a generous second-floor primary suite. Two additional bedrooms and a full bath comfortably accommodate family and guests. Outside, a large deck overlooks landscaped grounds with native plantings, stonework, and a fire pit gathering area. A full walk-out basement is perfect for both a work space and storage. Whether you’re searching for a year-round home, vacation retreat, or investment opportunity, this property offers something increasingly rare on Martha’s Vineyard: a home with genuine character, generous living space, and the comforts of modern living.

41 Cook Road, Tisbury

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.
$1,690,000
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 Road, Tisbury

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.
$1,175,000
3 Beds ⋅ 1 Baths ⋅ 73524099 MLS
This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other. Many attractive features include hardwood floors and Indian tile throughout, a large inviting mahogany deck off the front of the house overlooking a koi pond, fully owned solar panels that have covered the electrical costs for the past five years, a nitrogen reducing septic system, a full unfinished walkout basement and a large detached shed. This property is deed restricted to year-round housing and is part of the Daggett Ave. Homeowner’s Association which has a ninety-nine-year ground lease agreement.

299 Daggett Ave Unit A, Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 73503832 MLS ⋅ ['Tashmoo Cove'] BLDG.
END UNIT WITH PRIVATE DRIVEWAY IN TASHMOO WOODS. Well-maintained 3BR/3BA condo offering rare privacy, space, and a single-family feel in one of Vineyard Haven’s most desirable communities. End unit with private driveway, one-car garage, and extra storage. Mature plantings, including 24 added trees, enhance the setting. Open layout with granite kitchen and high-end appliances flows to dining area and private deck overlooking woodlands. Living room with wood-burning fireplace. First-floor bedroom and full bath add flexibility. Upstairs, primary suite with soaking tub and separate shower; second bedroom with nearby full bath. Recent updates include new 30-year roof and gutters (April, 2026). Amenities include tennis, heated pool, playground, basketball, private dock on Lake Tashmoo, and beach access, plus full exterior maintenance and landscaping for easy, turnkey living.

261 Sandpiper Lane Unit 12, Tisbury

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.
$7,500
3 Beds ⋅ 2 Baths ⋅ 73493947 MLS
Located off of Edgartown-Vineyard Haven Road, close to down-town and bike path, this 3 bedroom, 2 bath property is being offered year round to the right tenants. The home has been completely renovated, is being offered fully furnished and features an open floor plan with wood floors on the first level, wall to wall carpet in the upstairs bedrooms and an in-ground pool in the backyard. Available September for 1 year lease.

43 Edgartown Road, Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$1,975,000
3 Beds ⋅ 3 Baths ⋅ 73481021 MLS
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: 29 and 33 Lagoon Pond Road are also available as a package offering for $3,295,000. Showings are limited to turnover days - please inquire with listing agent.

33 Lagoon Pond Road, Tisbury

Listing courtesy of Listing Agent: Madelyn Silvia from Listing Office: Wallace & Co. Sotheby's International Realty.
$4,695,000
3 Beds ⋅ 2 Baths ⋅ 73478787 MLS
Downtown Vineyard Haven with Harbor Views. Positioned between the energy of Main Street and the quiet prestige of West Chop, this 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. 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.

16 Frog Hollow, Tisbury

Listing courtesy of Listing Agent: Rose Ryley from Listing Office: Wallace & Co. Sotheby's International Realty.
$18,840
3 Beds ⋅ 3 Baths ⋅ 72854056 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less formal TV and entertainment room. There is a large master bedroom suite on the first floor and two bedrooms on the second. A spacious patio overlooks a shady lawn. Take your choice of two outside showers. And this house is just a few blocks from picturesque downtown Vineyard Haven. This is a beautifully maintained perfect Vineyard property.

21 William St Vh430, Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$12,000
3 Beds ⋅ 2 Baths ⋅ 72852720 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three bedroom two bath condo is just a short walk to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!Amenities include Direct TV DVD set up. There is an open wifi signal in the building.

223 Sandpiper Lane Vh405, Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$10,000
3 Beds ⋅ 2 Baths ⋅ 72853547 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming 3 bedroom home offers open living, dining and kitchen space that open to a screened-in porch and patio. You are located in a peaceful setting yet with-in walking distance to Lake Tashmoo, town beaches, and the Vineyard Haven Village for dining, shopping and theater.

100 Franklin Terrace Vh411, Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

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