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.
Built in 2016 by Squash Meadow Builders, this exceptional five bedroom Colonial sits moments from the sandy shores of Tashmoo Beach on Vineyard Sound. Spanning four levels, it blends timeless architecture with modern comfort. The main floor offers open living with gas fireplace, a gourmet kitchen with custom built-ins and bench seating, and a sunlit sunroom for relaxed coastal living. A private first floor primary suite adds convenience. Upstairs, a bedroom suite with private bath joins three guest rooms sharing an updated bath. The finished third level provides a large bunk room, while the lower level features media room, gym, and storage. Outdoors, the sunroom opens to a pergola covered stone patio and saltwater pool framed by a classic stone wall. Lush landscaping, hydrangeas, outdoor fireplace, garage, and solar panels complete this turnkey Martha’s Vineyard retreat near one of the island’s most beloved beaches.
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.
In a peaceful Vineyard Haven setting just moments from town, 50 Lantern Lane offers a refined take on classic island living. Privately sited in a quiet enclave yet only one mile from Main Street, Owen Park Beach, and dining and just 1.2 miles from the ferry—this property blends convenience with serenity. The three bedroom, two bath residence spans 1,040 square feet and features a thoughtfully designed layout, including a sought after first floor bedroom. Sun filled living and dining spaces open seamlessly to outdoor decking and a tranquil backyard, creating an effortless indoor-outdoor lifestyle synonymous with Martha’s Vineyard. Modern comforts include an efficient heat pump system with mini-split heating and air conditioning. An unfinished lower level provides storage and laundry, while the outdoor shower and private yard complete the quintessential Vineyard experience.
A unique opportunity to own a one of a kind property complete with fourteen bedrooms, flanked with large picture windows and water views from all three living levels. Currently being run as a state licensed, private pay, assisted living facility. In addition to the fourteen bedrooms and twelve full baths and one half bath, in the main building, there is a private owners apartment on the first level. The potential opportunity to subdivide this parcel only adds value to this well-rounded offering. The property is being offered turn key with the opportunity to own a very profitable business. This offering is for both the current business and the real estate. Just a short distance to downtown Vineyard Haven, the harbor and the ferry, look no further for your future investment! *Note: This offering is for the real estate and the business, seller potentially willing to separate the two - please inquire with the listing agent for more information.
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!
The Colonial Style home with wrap around porch is beautifully maintained and nicely sited on almost a half acre. The first floor is thoughtfully designed and offers an open floor plan that includes an ample mudroom with half bath and is just off the side porch that takes you into the well equipped kitchen with a center island, stainless appliances, custom cabinetry and dining room with sliders to a peaceful and private deck. Living room offers a comfortable space for TV and relaxing. There is also nice size first floor primary with walk-in closet and spacious en-suite bathroom. The grand entryway takes you to the second floor which offers a second primary bedroom with walk-in closet and en-suite bath. There are two guest rooms that share bath and second floor laundry. Wood and tile floors throughout, propane FHA with A/C. The walkout basement offers almost 10' of ceiling height and is ready to be finished off for additional living space, workshop or office.
Find your sweet spot in this charming starter home, ideally located on a quiet street yet within an effortless walk of everything. Forget the car and get your steps in! You're a short jaunt to essentials like Cronig's Market and Shirley's Hardware, AND local favorites including The Maker, Black Dog Cafe, Island Fresh Pizza, Pie Chicks, and Island Adventures Mini Golf. Also within walking distance is the newly renovated Tisbury School! The interior delivers classic warmth, showcasing mellow wide pine floors in the living areas. Enjoy the convenience of an efficient kitchen with deck access to the back yard, a cheerful updated bathroom, and comfortable carpeted bedrooms. Need more space? A 3-bedroom septic system is being designed by Sourati Engineering. And the full, dry basement is a blank canvas, offering massive potential. This is your affordable opportunity to settle on Martha's Vineyard! Schedule your showing!
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.
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.
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!
3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! A rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 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 your mortgage. The main house features a stunning sun-room, a cheerful efficient kitchen, and a sweet living room anchored by a beautiful stone fireplace. The main house has been emptied out 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, radiating a clean and bright atmosphere. Situated on a spacious corner lot, the site is large enough to support a 5-bedroom septic system; a design is currently being finalized by Sourati Engineering (buyer to be financially responsible for the upgrade). Other features include oak floors, 2 decks, a vintage garden shed, and a full dry basement.
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.
Tisbury is located in Massachusetts. Tisbury, Massachusetts has a population of 4,744. Tisbury is less family-centric than the surrounding county with 12.32% of the households containing married families with children. The county average for households married with children is 27.66%.
The median household income in Tisbury, Massachusetts is $55,938. The median household income for the surrounding county is $77,392 compared to the national median of $69,021. The median age of people living in Tisbury is 52.9 years.
The average high temperature in July is 80.1 degrees, with an average low temperature in January of 22.6 degrees. The average rainfall is approximately 47.4 inches per year, with 24.2 inches of snow per year.
