Tisbury, MA Real Estate Search

Tisbury, MA 5 Bedroom Homes for Sale

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Newest Tisbury, MA 5 Bedroom Homes for Sale

$1,995,000
5 Beds ⋅ 3 Baths ⋅ 73560676 MLS
Ideally situated just minutes from the ferry, downtown Vineyard Haven, and West Tisbury, this charming, meticulously maintained property offers exceptional flexibility for year-round living, seasonal escape, or income potential. The main residence features three bedrooms and an inviting open-concept floor plan, seamlessly connecting an updated kitchen, living room, and dining area, perfect for entertaining or relaxed island living. Expansive decks extend the living space outdoors, overlooking mature plantings and beautifully established garden areas throughout the property. The home is powered by an owned 5kw solar panel system serving the entire property, offering energy efficiency and reduced utility costs. Agent has a list of detailed upgrades upon request. Adding remarkable versatility, a 900 square foot barn style studio offers space for a home office, artist's studio, workshop, or creative retreat, while a private two bedroom garden apartment, complete with its own separate entrance, provides excellent rental income potential or comfortable accommodations for extended family and guests. Ample parking and move-in ready condition round out this rare combination of location, character, and income producing flexibility on Martha's Vineyard. Please note: the property is located within the Vineyard Haven watershed, and a new or upgraded nitrogen-mitigating septic system will be required.

135 Mayflower Lane, Tisbury

Listing courtesy of Listing Agent: Kathleen Dawson from Listing Office: Donnelly + Co..
$2,695,000
5 Beds ⋅ 4 Baths ⋅ 73560291 MLS
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.

124 Main St., Tisbury

Listing courtesy of Listing Agent: Idalyn Macchia Gilstad from Listing Office: Wallace & Co. Sotheby's International Realty.
$3,295,000
5 Beds ⋅ 4 Baths ⋅ 73554212 MLS
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. Tenants in place. Showings are limited to turnover days - please inquire with listing agent.

29 and 33 Lagoon Pond Road, Tisbury

Listing courtesy of Listing Agent: Madelyn Silvia from Listing Office: Wallace & Co. Sotheby's International Realty.
$2,195,000
5 Beds ⋅ 4 Baths ⋅ 73511187 MLS
Tucked back from scenic Lake Street, this distinctive home offers privacy and charm on a landscaped 0.7 acre lot with mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm, inviting feel. The four-level design provides flexibility and character. The main level features a spacious kitchen with a center island open to the dining area, and a sunken living room with floor-to-ceiling windows overlooking the trees. A large screened porch extends the living space outdoors. Two bedrooms, a full bath, and laundry complete this floor. Upstairs, a dramatic hallway leads to a generous primary suite with a spacious bath and additional laundry. The third level offers a private guest suite with living area and bath. The finished lower level includes added living space, bath, and walkout. Convenient to the public boat landing on Lake Tashmoo, the Lake Street tennis and pickleball courts and just a short distance to Downtown Vineyard Haven.

159 Lake Street, Tisbury

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.
$1,595,000
5 Beds ⋅ 3 Baths ⋅ 73476994 MLS
Located in a quiet enclave off Main Street, Vineyard Haven and just a half-mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for entertaining. The design is casual but practical, evidenced by the well-appointed kitchen which offers direct access to the expansive deck. With separate finished living quarters on the garden level, the home easily accommodates guests and multi-generational living. Mature plantings bloom on stone-scaped retaining walls and evergreen trees provide ultimate privacy. Moments from the harbor, shops, and ferry, and yet this property also offers seclusion and privacy, a rare combination at this price point. Offered partially furnished.

22 Old Lighthouse Road, Tisbury

Listing courtesy of Listing Agent: Jessica Holtham from Listing Office: Wallace & Co. Sotheby's International Realty.
$7,950,000
5 Beds ⋅ 3 Baths ⋅ 73476753 MLS
A rare opportunity -- a Vineyard harbor front property with a Victorian gambrel cottage restored to its original grandeur of a century ago, an expansive front yard, 180 degree commanding views of the active harbor, private sandy beach, and unmatched serenity. You have the opportunity to own one of the finest estates gracing the Vineyard Haven harbor front -- so admired by all visitors to the Vineyard. The property, located on a private way in the historic Hatch Road neighborhood, is a short distance to downtown Vineyard Haven and the West Chop Club. The home, built in 1900, was the summer residence of Leland and Carol Powers who named their estate ''The Mooring.'' Enjoy the magnificent views and sounds from the wrap-around porch: spectacular sunrise over East Chop; tell time by the passing ferries; see youngsters learn the art of sailing from the Yacht Club; see the Black Dog tall ships raise their sails in front of you; watch family members and guests enjoy lawn games, and swimming.

33 Goethals Way, Tisbury

Listing courtesy of Listing Agent: Buder Team from Listing Office: Sandpiper Realty, Inc..
$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

Listing courtesy of Listing Agent: Erin Leighton from Listing Office: Compass.
$13,500
5 Beds ⋅ 6 Baths ⋅ 73408313 MLS
** SUMMER WEEKLY RATE ** Private and luxurious BRAND NEW contemporary chic 5 BED 5.5 BATH home perfectly situated close to downtown Vineyard Haven yet set amongst a rural and peaceful WEST CHOP adjacent neighborhood. Indulge and unwind in the PRIVATE HEATED SALTWATER IN-GROUND POOL surrounded by opulent outdoor living and dining area highlighted by covered al-fresco kitchen, BBQ grill and bar - fully fenced for aded privacy. Adventure to nearby beaches; Owen Little, Tashmoo and Eastville Beach - all within minutes from the home. Revel in the boutique shopping and world-class waterfront dining all within close proximity to the home. The expansive and luxurious interior features gourmet chef kitchen, multiple living and gathering spaces suitable for large groups. Set the ambiance with dramatic gas fireplace. Customizable climate throughout. Fun loving lower level game room enhanced with bar and kitchenette. Professional quality gym. Price is weekly estimate. Taxes and fees adtl.

14 Bernard Circle, Tisbury

Listing courtesy of Listing Agent: Allison Cameron Parry from Listing Office: Douglas Elliman Real Estate - Nantucket.
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