luxury real estate for sale Vineyard Haven, United States

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.

Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers just over 2,800 square feet of living space, plus an additional 700+ square feet of newly finished recreation space above the two-car garage, with its own private entrance and second-floor deck. The inviting first floor is designed for both comfortable living and entertaining, featuring a spacious kitchen with a center island and abundant counter space. The adjacent dining room offers a warm gathering space with a wood stove, while glass doors open to a wood deck and bluestone patio for seamless indoor-outdoor living. Multiple sitting areas, a living room with a gas fireplace, and a private office provide plenty of space to relax or work. Upstairs, two guest bedrooms share a recently updated bathroom, while the spacious primary suite offers a walk-in closet and a large, light-filled bathroom with a soaking tub and tiled shower. The primary bedroom and bathroom feature radiant-heated floors, adding an extra level of comfort and warmth. Additional amenities include a two-car garage and half basketball court, making this a versatile home with plenty of space for guests and entertaining. Conveniently located near Downtown Oak Bluffs and Farm Neck Golf Club, this property offers an ideal setting for enjoying all that the Island has to offer.

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.

Downtown Oak Bluffs B1-zoned parcel offering a rare mixed-use development opportunity in one of Martha’s Vineyard’s most iconic and active locations. Conveniently located near Inkwell Beach, Oak Bluffs Harbor, the Steamship Authority, day-trip ferry services, Circuit Avenue, and Ocean Park. This level lot includes an existing poured concrete foundation and Martha’s Vineyard Commission–approved plans by Sullivan & Associates Architects for a classic Vineyard-style, 2.5-story mixed-use building. The design includes ground-floor commercial space and two one-bedroom residential apartments, creating three rentable units in total. With plans in place and foundational work already completed, the property offers a clear path forward as a mixed-use development or, alternatively, the opportunity to construct a traditional two-bedroom residence in downtown Oak Bluffs.

A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive access to the association’s private dock on Sengekontacket Pond, ideal for kayaking, paddleboarding, and more. This offering also includes a highly coveted stockholder membership to Farm Neck Golf Club, making it a truly unique and valuable investment.

Over 3 acres in the West Tisbury section of Makonikey. This buildable lot is a short distance from the Lower Makonikey Association beach. The prime home site on this property was recently cleared to reveal beautifully contoured land with several ancient white oak trees. The property is situated in an area of several multimillion-dollar homes and will accommodate a house, a guesthouse, and a swimming pool. Note: The lot is most easily accessed via Chappaquiddick Ave, where the cleared area is easily visible on the left.

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 Studio with fireplace. 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. The current septic system meets all regulations and is designed for four bedrooms. Converting the Studio into an ADU is possible, and the permitting path forward has been identified by the building inspector. Enjoy effortless access to Lambert’s Cove Beach, 7a Foods, State Road Restaurant, and all the iconic West Tisbury landmarks.

Located on a quiet cul-de-sac in a private Edgartown neighborhood, this half-acre parcel offers the perfect setting for your Martha's Vineyard home. Centrally located, the property provides easy access to the bike path and State Forest walking trails. With the recent Massachusetts Affordable Homes Act, this lot is now buildable and will include an approved 3-bedroom septic plan. The site allows for a home of up to 1,850 sq. ft. of heated living space. Use as a seasonal residence or short-term rental is not permitted, ensuring a stable year-round neighborhood setting. Please note, the property may not be used as a seasonal residence or short-term rental. An excellent opportunity to design and build your future home on Martha’s Vineyard.

A peaceful retreat close to Edgartown's amenities, thoughtfully updated and refreshed with a new kitchen and light-filled living spaces, this four bedroom three bath home offers an easy, relaxed setting for family and guests. The main body of the home features one downstairs bedroom with two additional bedrooms upstairs plus a flex space with balcony, and a fourth bedroom with full bath and kitchenette located above the attached garage for a separate guest retreat. The walkout basement provides storage, laundry and future potential. A versatile property thoughtfully designed for comfortable year-round living and quintessential Vineyard summers. Bold Meadow community tennis & pickleball courts nearby and abutting State forest bike path and hiking trails right from your back door.

Introducing the E Building at Lighthouse Station, Woods Hole's premier 55+ coastal community, with completion anticipated in late fall. Designed for effortless single level living, this beautifully appointed condo offers approximately 1,565 square feet, two bedrooms, and 2½ baths. The heart of the residence is an inviting open concept family room and kitchen featuring SubZero and Wolf appliances. Every detail reflects quality craftsmanship and thoughtful design. Adding to the coastal lifestyle, a one year boating membership to the Flying Bridge Boat Club is included, making it easy to experience the beauty of Vineyard Sound. Life at Lighthouse Station extends well beyond your front door. Residents enjoy an on-site fitness center, beautifully maintained grounds, and the convenience of being just moments from the shops, restaurants, waterfront, and cultural attractions of Woods Hole Village. Lighthouse Station is more than a residence. It is an opportunity to embrace the very best of Cape Cod.

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.

More than a luxury townhome, Lighthouse Station offers a lifestyle that is rarely available on Cape Cod. Perched on 5.3 acres overlooking Little Harbor and Vineyard Sound, this exclusive 55+ community combines elegant coastal living with the convenience of being just a short stroll from the restaurants, shops, ferry, beaches, and world renowned oceanographic institutions that make Woods Hole one of New England's most cherished seaside villages. Enhancing this extraordinary offering is a one year membership to the new Flying Bridge Boat Club at Woods Hole Marine, with the possibility of securing a boat slip for those wishing to keep their boat nearby. Designed for effortless living, this newly constructed residence offers 2712 square feet of thoughtfully planned living space, plus a 900 square foot finished lower level. Three ensuite bedrooms, a private home office, two separate living areas, and dual laundry areas create an ideal layout for everyday comfort while providing exceptional privacy for family and guests. A soaring entry foyer leads to the open concept great room and professionally designed kitchen with Sub Zero, Wolf and Cove appliances. The main level also features a mudroom with laundry, powder room, and a spacious primary suite. Upstairs, two additional ensuite bedrooms provide comfortable guest accommodations, while the finished lower level offers a separate family room and flexible space for entertaining, hobbies, or extended stays. Nine foot ceilings, wide plank wood flooring, and custom cabinetry reflect the quality and craftsmanship found throughout the home. Begin your mornings with coffee on the private deck and spend your afternoons strolling into Woods Hole Village for lunch, dinner, waterfront activities, or a ferry ride to Martha's Vineyard. Lighthouse Station is more than a place to live. It is an opportunity to embrace the very best of the Cape Cod lifestyle, where luxury, convenience, boating, and the charm of Woods Hole come together in one remarkable community.

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 an acre of beautifully landscaped grounds, this estate offers a rare combination of privacy, refined living, and exceptional proximity to all that makes Martha’s Vineyard special. Bordering Land Bank conservation land and overlooking the picturesque fields of Morning Glory Farm, the property enjoys a peaceful pastoral setting with vibrant flower gardens and expansive outdoor living spaces. Just moments from the bike path, Downtown Edgartown, and South Beach, this exceptional compound offers the best of both worlds. With more than 4,000 square feet of living space across the main house, guest house, and detached garage with office above, there is ample room for both gathering and privacy. The recently renovated four-bedroom main residence is thoughtfully designed for comfortable living and entertaining. A dramatic living room with vaulted ceilings and a gas fireplace opens through sliding doors to an expansive deck overlooking the pool and outdoor kitchen. The dining room features soaring cathedral ceilings and direct deck access, while the beautifully renovated modern kitchen offers generous space for entertaining. A cozy den just off the kitchen provides a quiet retreat. The second floor is dedicated to the private primary suite with a renovated bath, while the lower level offers three additional bedrooms and two full bathrooms. The newly built two-bedroom guest house delivers an equally inviting experience, with cathedral ceilings accented by exposed beams, a modern kitchen, a spacious living room, a full bathroom, and laundry. Outdoor living is at the heart of this remarkable property. A heated infinity-edge pool and spa create a resort-like atmosphere, surrounded by beautifully manicured grounds and gardens with views across the working fields of Morning Glory Farm. A detached garage with an office and half bath above provides a versatile space for work or quiet retreat, complemented by an additional garage attached to the main house. Combining exceptional privacy, multiple living spaces and stunning farm views, 29 Llewellyn Way is a distinctive Vineyard compound designed for effortless year-round living and unforgettable summer gatherings.

A Rare Edgartown Opportunity — Privacy, Proximity & Possibility. Tucked away at the end of a private setting on Upper Main Street, this almost one acre parcel offers a rare opportunity to create your own Edgartown retreat within easy walking distance of downtown. Set well back from the road, the property provides a wonderful sense of privacy and seclusion while being remarkably close to the restaurants, shops, galleries, harbor and village life that make Edgartown so desirable. The property offers the potential to build a main residence and guest house, with the two structures together supporting up to seven bedrooms, along with the ability to add a pool and create the quintessential island compound. A small, older guest quarters and shed currently occupy the property and could be removed to make way for a thoughtfully designed new vision. For those seeking the best of both worlds, a private setting with the convenience of town just moments away this parcel of land presents an exceptional opportunity to create a custom Edgartown property tailored to your lifestyle. Bring your architect and imagine what could be created on this special piece of land.