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$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.
$1,450,000
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. The main house has a nice, finished area for storage.

21 W Spring St, Tisbury

Listing courtesy of Listing Agent: Casandra Hyland from Listing Office: Sandpiper Realty, Inc..
$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.
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 73481062 MLS
HOUSE + APARTMENT NEAR LAGOON! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This clean and bright, move-in ready property features a 3 BR, 1 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset the mortgage. The main house, featuring a wonderful sun-room, a cheerful efficient kitchen, and a comfortable living room anchored by a beautiful stone fireplace, has been emptied and awaits the new owner's touch (please refer to images showing digital staging). Both the main house and the apartment have been freshly painted throughout. Situated on a spacious corner lot, and located a short distance to down town and public Lagoon access, this property is a super value. SELLER WILL CREDIT BUYER THE COST OF A BRAND NEW 4BR SEPTIC SYSTEM AT CLOSING.

22 Oklahoma Ave, Tisbury

Listing courtesy of Listing Agent: Idalyn Macchia Gilstad from Listing Office: Wallace & Co. Sotheby's International Realty.
$1,350,000
4 Beds ⋅ 3 Baths ⋅ 73464793 MLS
Nestled on a quiet street just moments from the heart of Vineyard Haven, this well-maintained 4 BR, 3 BA home offers a winning blend of comfort, privacy, and classic island appeal. The sun-filled main level features an open-concept living area flowing seamlessly into a bright, updated kitchen with center island, ideal for everyday living and casual entertaining. Two 1st floor bedrooms and a full bath provide excellent flexibility for guests, home office space, or convenient one-level living, while upstairs offers two spacious en-suite bedrooms designed for privacy and relaxation. Outdoor living shines with a deck overlooking the yard, plus a lower-level bonus with laundry, storage, and workshop potential. Peacefully set yet close to it all, enjoy easy access to public beaches, Tisbury School, and just 0.5 miles to Main Street Vineyard Haven with shops, dining, and ferry access. Perfect as a year-round residence, second home, or investment opportunity—this property checks all the boxes!

116 Franklin Ter, Tisbury

Listing courtesy of Listing Agent: Pricila Ray from Listing Office: Keller Williams Realty.

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