Tisbury, MA Real Estate Search

Tisbury, MA Single Family Homes for Sale

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Newest Tisbury, MA Single Family Homes for Sale

$2,295,000
4 Beds ⋅ 4 Baths ⋅ 73575143 MLS
Nestled on an acre of beautifully landscaped grounds in a tranquil, park-like setting, this home is tucked away on a quiet lane within an established neighborhood. Located just a quarter mile from miles of Land Bank walking trails and less than two miles from Main Street, it offers the perfect opportunity to embrace the Vineyard lifestyle, just minutes from the vibrant center of Vineyard Haven. Thoughtfully designed for both everyday living and entertaining, the main level boasts hardwood floors, high ceilings, and lots of windows that bathe the living areas and bedrooms in natural light. The kitchen serves as the heart of the home, featuring a center island and a dining area that opens onto a deck and attached gazebo—ideal for outdoor dining and gatherings. The inviting living room, complete with a propane fireplace, provides a warm and welcoming space. Three bedrooms—including a primary with ample closet space and a newly refinished bath are all located on the first floor. Additional highlights include new stainless-steel appliances, a Bertazzoni stove, Andersen windows, renovated baths, fresh paint, refinished floors, custom window treatments, plantation shutters, and a generator. This turnkey property is ready for immediate occupancy, allowing you to settle in and enjoy from day one. On the garden level, you'll find versatile space for additional living, relaxation, or exercise. The family room includes a half-bath and sliders that open to the patio and outdoor shower. A separate guest suite complete with bedroom, den, full bath, and kitchenette provides flexible accommodations for visitors. Meticulously maintained inside and out, this home is ready to welcome its next owner.

125 Mayflower Ln, Tisbury

Listing courtesy of Listing Agent: Courtney Marek from Listing Office: Sandpiper Realty, Inc..
$2,095,000
4 Beds ⋅ 4 Baths ⋅ 73571249 MLS
COMING SOON! Welcome to 18 Sylvan Avenue, a delightful, custom-crafted four-bedroom, four-bath, contemporary-style home set at the end of a quiet neighborhood road in Vineyard Haven. Surrounded by eight acres of conservation land, the property offers a peaceful setting with a spacious wraparound deck overlooking the natural landscape. It truly feels like its own private enclave, both inside and out. The home is in pristine, move-in-ready condition and has been thoughtfully renovated and meticulously maintained by the current owners. A welcoming entry leads directly into the open-concept space where a well appointed living room with fireplace flows into the dining area and kitchen. Positioned to the right of the entry is the primary bedroom suite, while two additional bedrooms and two bathrooms are tucked beyond the kitchen on the opposite side of the home, creating a functional and well designed layout which maximizes privacy. A finished lower level with a full bathroom and laundry provides additional flexible living space or a fourth bedroom. Skylights and sliders throughout the home fill the interior with natural light and create an easy connection to the multiple decks, beautiful mature gardens and woodlands. With an impressive rental history, this unique property is offered turnkey, making it an ideal opportunity as a year-round residence, Island retreat, or investment property. A true gem, conveniently located only 1.5 miles to Vineyard Haven’s Main Street shops, restaurants and ferry terminal, and only 5 miles to all that downtown Oak Bluffs has to offer! Showings begin on September 25th. Please note there is ducted HVAC and mini splits for both heat and AC as well as radiant heat in the floors throughout both levels. Property is located in the Lagoon Pond Watershed, septic will require an upgrade after transfer. Seller will include a four bedroom septic design.

18 Sylvan Avenue, Tisbury

Listing courtesy of Listing Agent: Madelyn Silvia from Listing Office: Wallace & Co. Sotheby's International Realty.
$6,150,000
6 Beds ⋅ 7 Baths ⋅ 73565263 MLS
Tucked away on a quiet street in coveted West Chop, this pristine property offers exceptional privacy, stunning scenery, and easy access to downtown Vineyard Haven. Designed for effortless indoor-outdoor living, this sophisticated compound combines timeless charm with every modern amenity. The first floor features an inviting open-concept layout ideal for both relaxed family living and entertaining. The kitchen overlooks the dining area, an intimate sitting area, and a versatile game and reading area beyond. The spacious TV and family room features custom built-in bookcases and French doors that open onto a bluestone patio and the pool area beyond. A generous screened porch provides additional living space. Completing the first floor is a large guest bedroom with an ensuite bath, along with a powder room, pantry, mudroom, and laundry room. Upstairs, the gracious primary suite features vaulted ceilings, a sitting area, and a luxurious bath with a soaking tub. There are two additional guest bedrooms, each with an ensuite bath. A private sun deck overlooks the pool and beautifully landscaped grounds, offering a wonderful spot to relax and enjoy distant water views. A dedicated office with water views toward Woods Hole and the Elizabeth Islands provides an inspiring setting for work or quiet retreat. Above the garage, a separate one-bedroom apartment offers a full kitchen, bath, and laundry, with convenient interior and exterior access. The living space in the apartment is currently being used as the sixth bedroom. Outside, the property transforms into a private oasis. The upper garden patio features an inviting sofa seating, while a stone staircase leads down to the heated 20' x 40' pool with spa. The expansive pool terrace is furnished with comfortable loungers and the pool cabana provides additional seating and a welcome retreat from the sun, all surrounded by lush, mature plantings. Other amenities include a gym, two enclosed outside showers and a pool powder room. With its exceptional privacy, generous living spaces, water views, pool and cabana, guest accommodations, this stunning property is truly one of the Grand Dames of West Chop.

59 Hagerty Drive, Tisbury

Listing courtesy of Listing Agent: Carol Shore from Listing Office: Donnelly + Co..
$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..
$1,600,000
4 Beds ⋅ 4 Baths ⋅ 73563290 MLS
Expanded cottage with in-law suite, garage, and detached studio. On the way to West Chop, it is equidistant to Downtown Vineyard Haven, the flagpole at West Chop, Mink Meadows Golf Club, and Vineyard Haven Yacht Club. This 4 bedroom, 4 bathroom property offers a flexible floor plan, including a private inlaw wing complete with its own entrance, kitchen, living room, full bathroom, and bedroom—perfect for extended family or guests. There are two driveways. The home also features a garage and a finished basement offering excellent storage or future expansion potential. A detached studio at the rear of the property provides wonderful overflow space for a home office, art studio, or guests. The property is only 2/10ths of a mile to the town beach at the end of Grove Ave, and half a mile to the town beach on Owen Little Way. Ready for a new owner's vision and updates, this well-located property presents an exceptional opportunity to enjoy the convenience and charm of this desirable neighborhood. This property is being offered "as-is." *Please note there is only AC in the primary bedroom wing addition.

528 Main Street, Tisbury

Listing courtesy of Listing Agent: Madelyn Silvia from Listing Office: Wallace & Co. Sotheby's International Realty.
$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.
$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.
$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.
$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..
$1,690,000
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.
$5,800,000
6 Beds ⋅ 9 Baths ⋅ 73525014 MLS
Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home for a client list that included Lady Diana Spencer. The historic main house has been completely modernized. There are 6 bedrooms spread out over almost 6000 square feet, a detached pool house, swimming pool, and Har-Tru tennis court. Wherever you are in this gracious home you will be blessed with sweeping views of the open fields, stone walls, and horses in the neighboring farm, a scene as if from a painting done in a previous century. Included within the 10 acres is a separate 3.3-acre parcel of land that will accommodate a full-size home. Association located dock on Lake Tashmoo!

31 Lambert's Cove Rd., Tisbury

Listing courtesy of Listing Agent: Idalyn Macchia Gilstad from Listing Office: Wallace & Co. Sotheby's International Realty.
$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..
$1,999,000
4 Beds ⋅ 3 Baths ⋅ 73516062 MLS
Nestled at 5 Pinetree Lane, Vineyard Haven, MA, this single-family residence in Dukes County presents a unique opportunity to own a piece of classic American architecture. Built in 1927, this home offers a blend of vintage charm and comfortable living. The residence features three full bathrooms, providing convenience and privacy for all occupants. Imagine mornings where everyone can prepare for the day without the rush, and evenings where relaxation is never compromised. The thoughtful design ensures that personal space is always readily available. With four bedrooms, this home provides ample space for rest and rejuvenation. Envision each room becoming a personalized sanctuary, tailored to individual preferences and needs. Whether it's a tranquil space for sleep, a vibrant area for hobbies, or a practical room for remote work, these bedrooms offer the flexibility to adapt to any lifestyle. The 2730 square feet of living area unfolds to provide a comfortable and inviting environment.

5 Pinetree Lane, Tisbury

Listing courtesy of Listing Agent: Kristin Francoeur from Listing Office: Gibson 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.
$1,250,000
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.
$1,975,000
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.
$1,999,000
4 Beds ⋅ 3 Baths ⋅ 73480830 MLS
Blending 1920s charm with modern luxury, this beautifully renovated home is tucked into the coveted West Chop area of Vineyard Haven. Just steps from a neighborhood beach on the pristine shores of Vineyard Sound, it offers an elegant mix of historic character and contemporary comfort. A thoughtfully designed layout features generous living spaces centered around a chef’s kitchen with custom cabinetry, high-end appliances, and refined finishes. Open living and dining areas flow seamlessly, enhanced by updated systems and central air. Upstairs, the serene primary suite includes a spa-like tile bath with soaking tub, while two guest bedrooms share a stylish full bath with laundry. Nautical details like a compass rose stained-glass window add charm. The finished lower level provides a large additional bedroom and flexible living space. Outside, a mahogany deck overlooks the newly landscaped yard with outdoor shower and entertaining areas. Just minutes from downtown Vineyard Haven.

5 Pine Tree Lane, Tisbury

Listing courtesy of Listing Agent: Alyssa Halisky 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.
$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..
$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.
$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.
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