luxury houses for sale Vineyard Haven, United States

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.

WATERFRONT WITH DOCK – Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilities are endless. Enjoy water views from virtually every room as the home's spectacular waterfront setting seamlessly extends to your private sandy beach and deep-water dock, offering direct access for boating, swimming, paddle boarding, or simply relaxing by the water's edge. A truly special legacy property offered for the first time in over 50 years where history, charm, and an unparalleled waterfront lifestyle come together.

Set on a generous 0.3-acre lot in desirable Oak Bluffs, this property offers exceptional potential just moments from Vineyard Sound. A newly installed 6-bedroom septic system opens the door to a variety of expansion opportunities. The home is thoughtfully designed with two separate living areas, ideal for guests or rental possibilities. The main living space features hardwood floors throughout, a spacious living room with a fireplace, kitchen, sunroom, and a primary bedroom with a full bath. An additional shared living room serves as the central gathering space between the two wings of the home, creating a seamless and functional layout. The secondary living area includes a kitchenette, dining space, guest bedroom, and bathroom. The bathroom is currently unfinished, providing the next owner the opportunity to customize it to their taste. Upstairs, the second level boasts high ceilings, abundant natural light, a guest bedroom, and a private office space. Additional highlights include a two-car garage, a large rear deck, and a private backyard setting. An excellent investment or renovation opportunity in Oak Bluffs, offered as-is.

Recently updated Oak Bluffs ranch-style home ideally located near Downtown and Oak Bluffs Harbor. Step inside to discover vaulted ceilings and an airy open floor plan that seamlessly connects the living room, dining area, and a spacious kitchen featuring granite countertops and updated appliances. The private primary suite is thoughtfully positioned off the main living area and offers a full bath with in-suite laundry, plus its own separate exterior entrance, perfect for added privacy or guest flexibility. Two additional guest bedrooms and a full hall bath complete the interior layout. Outdoor living is equally inviting, with a charming front deck featuring built-in bench seating, a stone patio for entertaining, and a convenient storage shed. Recent upgrades include a new roof, updated flooring, and energy-efficient mini-split systems for heating and cooling. Move-in ready and perfectly suited for enjoying the Vineyard lifestyle.

Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a detached garage, and exclusive access to Hidden Cove's sought-after amenities, including a private boat launch. Just minutes from Oak Bluffs, Farm Neck Golf Club, beaches, and the bike path, this is a place where generations return to create the kind of Martha's Vineyard summers that never go out of style.

This enchanting artist-designed property is tucked away on 2.9 private acres in West Tisbury, a thoughtfully composed retreat with pastoral meadows, mature landscaping, and an unmistakable sense of intention and sophisticated taste. The two-bedroom, two-bathroom Main House is complemented by a spacious two-bedroom, one-bathroom Guest Studio with a fireplace, offering a combined 3,771 square feet of living space. A gunite swimming pool, gardens, expansive lawn areas, outdoor shower, and one-car garage complete the setting. Renovated in 2013 and equipped with central air conditioning, the property feels wonderfully secluded while remaining centrally located for convenient access to both up and down Island destinations. Future expansion to 12 bedrooms is possible with a septic upgrade, although the current system meets all regulations. Enjoy effortless access to Lambert’s Cove Beach, 7a Foods, North Tisbury Farm, State Road Restaurant, and all the iconic West Tisbury landmarks.

Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval, providing exciting possibilities for future expansion. A partially finished walk-out basement adds flexible additional space. Whether enjoyed as a year round residence or seasonal Island retreat, this property offers space, convenience, and potential. To add to this well rounded offering, this property is also being offered turnkey!

Set within the coveted Vineyard Meadow Farms community, this West Tisbury property presents a rare opportunity to own a thoughtfully configured compound in one of the island's most peaceful and sought-after settings. Privately sited on a generous parcel, the property is surrounded by natural beauty and offers a sense of calm that defines up-island living.The three-bedroom main residence is complemented by a separate two-bedroom guest house, creating a flexible and highly desirable arrangement for extended family, guests, or income potential. The layout lends itself effortlessly to both everyday living and entertaining, with each structure offering its own sense of space and privacy.A substantial garage adds meaningful utility, ideal for storage, a workshop, or accommodating island vehicles, an increasingly valuable feature in this location. The grounds offer ample room for outdoor living and future expansion, allowing the next owner to tailor the property to their vision.Surrounded by the natural beauty that defines the up-island experience, the property is just minutes from Long Point Beach, the protected landscapes of the Long Point Wildlife Refuge, scenic walking trails, and the serene waters of Long Cove Pond. Offering both privacy and proximity to some of Martha's Vineyard's most cherished outdoor destinations, this is a compelling opportunity to invest in a lifestyle of relaxation, recreation, and enduring value.*Select images may include virtual staging to illustrate potential use and design.

House & Guesthouse near Long Point Beach! The Island's coveted south shore is just minutes from this charming West Tisbury compound, where the connection to nature is seamless. The main house sits high atop the trees and overlooks a park-like, fenced-in backyard, perfect for kids and dogs. The yard also encompasses a sweet vegetable garden, a storage shed, and outdoor shower. Inside, find an open floor plan with natural light streaming in from windows and skylights. The kitchen flows to the dining area, which flows to the spacious living room anchored by a wood-burning stove for cozy ambience. Also on this level is the primary bedroom with two closets, and a large full bathroom with a soaking tub and separate tiled shower. The larger, open loft upstairs offers versatile living space perfect for reading, television, or spillover guests. Downstairs on ground level is another full bathroom and two bedrooms plus a light-filled home office with a convenient exterior access. Other features for the main house are a new furnace and 4 mini splits for air conditioning. Last but not least, adding tremendous value to the property, is a beautiful, spacious guesthouse with every detail curated for comfort and style; central air and heat, a living room with a gas fireplace, a full eat-in kitchen, a bedroom with two closets, a full bathroom, a bonus attic room, and a deck perfect for bird watching while listening to the distant rhythm of the Atlantic! This property is not to be missed! Note: At closing Seller will credit Buyer for 4-bedroom septic system upgrade. See design by VLSE in documents.

Experience refined coastal living in this impeccably renovated modern condominium nestled within the tranquil enclave of Meetinghouse Village. This sophisticated end-unit residence lives with the ease of new construction, offering bright, sun-filled interiors and thoughtfully curated finishes throughout.Every detail has been meticulously upgraded—from new appliances, lighting, and mechanical systems to custom window treatments, energy-efficient window tinting, and enhanced insulation for exceptional year-round comfort. Beautifully reimagined bathrooms, a fully finished lower level, and three seamlessly integrated 50 smart TVs add both versatility and contemporary style.Step outside to a private bluestone patio with elegant landscape lighting, perfectly positioned beside a wooded side yard that offers a rare sense of privacy for condominium living.Ideally located just moments from downtown Edgartown's acclaimed restaurants, boutiques, beaches, and harbor, Meetinghouse Village also offers residents a community pool and generous guest parking. Move-in ready and impeccably maintained, this turnkey residence is equally suited as a year-round home, seasonal retreat, or investment opportunity.Easy to show.

On sheltered Eel Pond, with a large, licensed deepwater dock and direct access to Vineyard Sound and Buzzards Bay, this waterfront property presents a rare opportunity to create your own Woods Hole compound. Originally dating back to the 1820s, this classic New England home spans three separate dwellings - each with sweeping water views: a main 5-bedroom residence with a separate guest suite, plus two year-round cottages (one 2-bedroom and one 1-bedroom). Located on the village doorstep, with ample off-street parking and seclusion, you are moments from restaurants, shops, ferries, beaches, the vibrant harbor and renowned marine science institutions. Position, potential and provenance - and available for the first time in 70 years - this is a once-in-a-lifetime chance to establish your own Woods Hole legacy in a premium Cape Cod waterfront community.

Set on over a half an acre in Edgartown’s desirable Island Grove neighborhood, this three-bedroom, two-bath classic Cape offers an exceptional expansion opportunity in a convenient Katama location. The existing 1,560-square-foot home can be enjoyed as-is while plans are developed for a renovation, expansion, or new construction. With a connection to town sewer, the property can support up to seven bedrooms, creating potential for a substantial residence, pool, and accessory dwelling unit. Surrounded on two sides by common land, this lot offers a unique level of privacy. Association tennis courts are located nearby, with Morning Glory Farm, Edgartown Village, South Beach, shops, restaurants, and the harbor all within easy reach. A rare opportunity to create a custom Vineyard retreat in an established neighborhood.

A rare offering of extraordinary scale and architectural significance, this 22-acre Martha's Vineyard estate represents a category of ownership seldom available on the Island. Designed around privacy, natural beauty, and enduring craftsmanship, the living spaces encompass more than 9,500 square feet across multiple thoughtfully designed structures, creating an unparalleled setting for multigenerational living, private retreats, or legacy ownership. Altogether, the compound offers 11 bedrooms and 13 bathrooms across its collection of residences and guest accommodations. At its heart is the Robert A.M. Stern-designed main residencean architectural work by one of America's most celebrated architects, whose residential designs are prized for their timeless elegance and lasting value. Complementing the estate is the architecturally striking Pond House, completed in 2021, featuring cathedral ceilings, exposed beams, shiplap detailing, a dramatic stone fireplace, screened porch overlooking the pond, and beautifully appointed interiors that rival the finest boutique hotels. A 1,700-square-foot Amish barn includes additional living quarters, and private driveways serving both parcels provide exceptional flexibility while maintaining complete privacy throughout the property. Resort-caliber amenities elevate the experience, including a heated 20' x 60' swimming pool, an exceptional pool house with a fully equipped gym, sauna, massage room, and a screened porch with fireplace for effortless indoor-outdoor entertaining. Conveying with the property is coveted membership in the exclusive Boldwater Association, granting access to a private Atlantic Ocean beach, boat landing, tennis courts, and pickleballoffering the best of Vineyard coastal living without sacrificing the remarkable privacy of this inland sanctuary. This is far more than a luxury home. It is a private estate where architecture, landscape, and thoughtful design become the defining amenities. For the discerning buyer who values land, beauty, and architectural pedigree above a traditional waterfront address, this is an irreplaceable Vineyard legacy property unlike anything else available today. Off Edgartown West Tisbury Road via Pohoganot Road.