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.
Courtesy: Sandpiper Realty Inc
508-627-3737
MIXED USE PROPERTY WITH PROFESSIONAL OFFICES AND TWO-BEDROOM APARTMENT - Extensively renovated mixed-use property offering commercial + residential use in a high-visibility location on State Road in Tisbury. This versatile property presents a true live-work opportunity with strong income-producing potential.The first floor offers four offices including a reception area, 1.5 baths, and a kitchenette, with both front and side entrances. The second floor features a bright and sunny two-bedroom apartment with a full bath, living room, and kitchen--ideal for owner occupancy or rental income.The entire building has been renovated and includes heat and air conditioning throughout, off-street parking for multiple vehicles in the rear, and a yard. Seller financing available, please inquire!
Courtesy: Island Real Estate
508-693-4800
Here is your chance to be a Homeowner on Martha's Vineyard. MOVE RIGHT IN! This sunny end unit is being offered furnished! Spacious living area opens to an eat-in kitchen with a new Bosch dishwasher. Bedroom number one has a queen bed. Bedroom two has two single beds. Conveniently located within close proximity to Main Street shops, the ferry and bus terminal, and the scenic bike path that extends across the island. At the bottom of the hill you will find a recreation area with basketball hoops, volleyball net and swings! Could this be the opportunity that you have been waiting for to be a homeowner on the Island? Year-round living or investment home with a solid rental history. Additional financial information provided upon request.
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.
Courtesy: Island Real Estate
508-693-4800
The Premiere Townhouse at Tashmoo Wood. Elegantly renovated, this sun-filled end unit is fresh and modern with fine finish details. From the moment you step onto the expanded wrap-around deck, you will begin to see the fine craftsmanship of the property. Walk through the front entry and you will gain further appreciation for the meticulous attention to detail. Expansive windows fill the living area with light while providing a view to the side yard and fountain down below. Enjoy evenings on the deck or in front of the wood-burning fireplace. Any chef will be happy in the well-appointed kitchen with Thermador appliances that include a 5-burner cook top and double wall ovens, sizable island with seating, and counters topped with quartz. The kitchen affords views to the dining and living areas as well as out to the deck and yard. There is a first-floor room with an en suite bath. Pocket doors allow for the bath to be a powder room while providing privacy to the flex-room. Ascend the modern staircase to be wowed by the primary suite. The spa-like bath has double sinks and a make-up vanity. There is a glass-enclosed, tiled shower with multiple shower heads. The walk-in closet has been finished with hanging rods, shelves, and drawers. and there is a sliding door that opens to a balcony overlooking the yard. The second en suite bedroom has plantation shutters and a bathroom with a tub. Behind a pocket door, in the hall, you will find a well-organized laundry room with commercial-sized washer and dryer. White oak floors throughout the first and second level with tiled baths. Rinnai on demand water heater. Plantations shutters and custom shades throughout. There is an over-sized garage that is larger than many of the other units. With association amenities that include a pool with pool house, multiple tennis courts, playground, basketball court, private access area to Lake Tashmoo, and a beach on Vineyard Sound. If you are looking for luxury with the convenience of townhouse living, look no further than this truly spectacular unit.
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.
Courtesy: Wallace & Co. Sotheby's International Realty
508-627-3313
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 cafe 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. A rare opportunity to own directly on Vineyard Haven Harbor, with a mooring available and the best of Martha's Vineyard right outside your door.
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!
Courtesy: Portfolio Properties
508-627-7005
Country Living so close to Town! Lovely 4 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space . Open kitchen, dining & entertainment area. Sliders open to Large side deck. High Ceilings Wood floors Living Room with additional nook. Half bath. Interior stairs to lower level with office/bedroom, half bath, private exterior entrance and garage. 2nd floor has large primary bedroom with cathedral ceilings, walk through double closet and generous private bath with jacuzzi, separate shower and laundry facilities. Two additional bedrooms. 2nd full bath. Attic. Grassy areas on front and side of property. Small association off West Spring St. R10 Zoning. Propane FHW Heat Pump A/C Radiant Heat on lower level Town Water Title V 4 Bedroom Septic must be upgraded to Nitrogen reducing Septic. New design currently being worked on by Engineer will be provided to Buyer upon completion. Easy access to Town, Year round Ferry port, shops, restaurants, Tisbury School, Tashmoo Scenic Overlook, Amphitheatre and a direct route to up island towns.
Courtesy: Sandpiper Realty Inc
508-627-3737
This move-in ready four-bedroom, being offered fully furnished, delivers effortless living, simply bring your swimsuit and settle in. Featuring an open and inviting layout, the living space seamlessly extends to the large deck and heated pool, perfect for relaxing or entertaining. Conveniently located just one mile from the shops and restaurants of downtown Vineyard Haven and less than two miles from the sandy shores of Tashmoo public beach. With a strong rental history, it's perfectly suited as a year-round residence, vacation retreat, or investment property. The property is located within the Tashmoo Watershed District, and the septic system will require upgrades to comply with denitrification requirements.
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, a cheerful updated bathroom, and cozy carpeted bedrooms. Need more space? 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 now!
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.
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.
Courtesy: Compass Massachusetts, LLC
508-206-8726
NEW CONSTRUCTION - Designed by Outlands Design and built by McElhinney Construction, this home exemplifies modern coastal design. 34 Davis Street delivers the perfect balance of sophistication and relaxed island living. Positioned to offer both privacy and proximity to the Island's harbors, shops, and beaches. Spread across two thoughtfully designed levels, the interiors are bathed in natural light, highlighting the clean lines, open spaces, and high-end finishes throughout. Highlights include a chef's kitchen with Thermador appliances, a 9-foot island, and 7-inch oak flooring. The exterior is clad in timeless cedar shingles with crisp white trim, while expansive windows create a seamless indoor-outdoor connection. A walk-out unfinished lower level provides the option for a home office, gym, or media room. The professionally designed landscape plan by Contemporary Landscape allows you to customize the outdoor experience--whether adding a fire pit, pool, or spa. Perfect as a year-round residence, summer retreat, or investment property with strong rental potential, this home is truly an island gem. *Agent is owner.
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.
Vineyard Haven is located in Massachusetts. Vineyard Haven, Massachusetts 02568has a population of 2,258. Vineyard Haven 02568 is less family-centric than the surrounding county with 26.79% of the households containing married families with children. The county average for households married with children is 27.66%.
The median household income in Vineyard Haven, Massachusetts 02568 is $60,080. 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 Vineyard Haven 02568 is 58.8 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.
