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.
Classic Style Meets Timeless Charm - Located at the end of a lightly traveled lane and surrounded by stunning gardens and stone retaining walls, this residence provides a modern and spacious environment for comfortable island living. The home welcomes you with an open and bright layout, featuring sleek finishes and an abundance of natural light. The gourmet kitchen is a chef's delight that seamlessly connects with the living and dining areas. A cozy Family Room/Den is also located on the main floor. The second-floor primary bedroom is a private sanctuary, complete with a walk-in closet and a spa-like en suite bathroom. Outside, the meticulously landscaped yard provides a serene escape for outdoor relaxation and gatherings, offering a private retreat for enjoying the beautiful surroundings.*Note: The property is located in the Lagoon Pond watershed and will require an upgrade to an enhanced nitrogen septic upgrade. An approved septic plan PLUS a $35,000 buyer closing credit is included
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.
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.
128 Spring Street—just moments from the Tisbury School and downtown Vineyard Haven. Built in 2013 and sited on an ample 1/4-acre lot, the house features four bedrooms and two-and-a-half bathrooms, along with a separate first floor one-bedroom in-law apartment complete with a full bath—ideal for extended family, guests, or added rental flexibility. The central location offers convenience to schools, ferry, shops, and beaches, while the layout allows for privacy, adaptability, and long-term value. Few properties on Martha’s Vineyard offer this level of space, flexibility, and opportunity in such a walkable, well-connected neighborhood. Note: This property is also being marketed as part of compound with the abutting 1BR/1BA home located at 136 Spring Street.
A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street - Two adjacent properties being sold together create a flexible compound just moments from downtown Vineyard Haven. The 4-bedroom, 2-1/2 bath main house also includes a separate, 1-bedroom in-law/nanny apartment with a full bath. The guest house has 1 bedroom and 1 bath, with a 4-bedroom septic system allowing for expansion—ideal for guests or rental income. Perfect for multigenerational living, seasonal use, or year-round occupancy with income potential. Conveniently located near the ferry, school, shops, and beaches, this compound offers privacy, versatility, and long-term value. Live in one, rent the other, host with ease, or tailor both homes to suit your needs. A rare opportunity in one of the island’s most walkable, connected neighborhoods.
Newly priced ~ fully renovated building and move-in ready! Outstanding, year-round, two-bedroom condo on the ground level with dedicated parking, and conveniently located close to the ferry, shops, and restaurants on Main Street, Vineyard Haven. This building (Building A) is undergoing a complete renovation including a new roof, siding, windows and doors, trim, decks and steps. Enjoy this freshly updated unit in time for Spring! The common grounds feature colorful landscaping, picnic tables, grills, and a swimming pool with a distant peek at the Lagoon. This unit has been tastefully renovated, featuring new hardwood floors, an updated bathroom, updated kitchen appliances, and a freshly painted interior. Being sold furnished, this true gem is ready for immediate occupancy.
Welcome to this meticulously maintained 2+ bedroom, 3 bathroom end unit condo in Tashmoo Woods, built in 1998. The updated kitchen with granite countertops and high-end appliances opens to a dining room with a private deck overlooking lush woods. The first floor includes a den and a renovated bathroom. Upstairs, both bedrooms have ensuite bathrooms. Upgrades include propane heat, central air, a gas stove, an alarm system, and new Andersen sliding doors. Outside, 12 White Pine trees enhance privacy, with Belgian Block pavers, a flagstone walkway, and a large planting bed with a bird bath. The condo offers a private driveway, a 1-car garage with custom shelving, and extra storage for bikes and beach chairs. Tashmoo Woods amenities include tennis courts, a heated pool, a playground, a basketball court, a dock on Lake Tashmoo, and a private beach. Located in the Tashmoo Watershed area, the sellers are willing to contribute to the upgrade of a denitrification septic system.

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.