luxury seaside houses for sale West Tisbury, United States

Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to discover a custom circular staircase with dramatic floor to ceiling windows, leading to the upper living area flooded with natural light from the wall of south-facing windows. The living area with high ceilings and woodstove is a comfortable place to congregate, while the kitchen and open dining areas lend themselves to modern day living. Glass sliding doors open onto a spacious 2nd story deck giving the entire living space an intimate relationship with the outdoors. On the first floor there are three total bedrooms; two bedrooms sharing a full bath plus a primary bedroom with a full bath en-suite. Total square footage represents house (1,400 sq. ft.) and guest house (518 sq. ft.). A shared six (6) bedroom septic system services both houses.

Set high on the north shore with panoramic waterviews of Vineyard Sound and deeded private beach access, this secluded 9.8-acre property occupies a rare setting bordered by conservation land and the Menemsha Hills trail network. The spacious, meticulously maintained residence features a reverse floor plan that accentuates the natural light, soaring ceilings, and breathtaking views. The upper level includes an open-concept kitchen, dining, and living area, along with a private primary suite and dedicated office space. There is a large open deck and a screened porch o n this level, as well as a deck off the primary bedroom suite. Thoughtfully designed for both everyday living and entertaining, the home includes amenities such as air conditioning, a whole-house generator, an integrated sound system, outdoor lighting, and more. Outside, the grounds are equally impressive, featuring a tennis court, landscaped gardens with a water feature, and a large open meadow spanning several acres, all surrounded by mature woodland for exceptional privacy. No neighboring homes are visible from the property. There is ample room to add a swimming pool, and the parcel may offer subdivision opportunities. Ownership also includes rights to Brickyard Beach.

Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home for a client list that included Lady Diana Spencer. The historic main house has been completely modernized. There are 6 bedrooms spread out over almost 6000 square feet, a detached pool house, swimming pool, and Har-Tru tennis court. Wherever you are in this gracious home you will be blessed with sweeping views of the open fields, stone walls, and horses in the neighboring farm, a scene as if from a painting done in a previous century. Included within the 10 acres is a separate 3.3-acre parcel of land that will accommodate a full-size home. The property is part of the Tashmoo Farm Association which includes deeded access to the association dock on Lake Tashmoo and tennis courts.

Introducing a refined contemporary Chilmark beach house with water views and deeded access to Stonewall Beach on the Atlantic Ocean. The property is set within the storied Stonewall Road and Beach Association - where homes are held for generations and lifelong friendships take root - and offers a true sense of place and continuity. Built by South Mountain Company and thoughtfully renovated and significantly expanded in 2023, the home blends craftsmanship with modern comfort. Enjoy sweeping views of the Atlantic Ocean, Squibnocket Point, and Nomans Land island from both interior living spaces and outdoor vantage points. Designed for multigenerational living, the home offers multiple private zones - including a dedicated media room - allowing for both connection and retreat. This is a rare opportunity to own a meaningful piece of Chilmark—an offering not to be missed.

House & Apartment Near Lagoon! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This clean, bright, move-in-ready property features a 3 BR, 1 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 the mortgage. The main house, featuring a wonderful sunroom, an efficient kitchen, and a comfortable living room anchored by a beautiful stone fireplace, has been emptied 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. Situated on a spacious corner lot, and located a short distance to down town and public Lagoon access, this property is a super value. Seller will credit the buyer the cost of a brand new septic system at closing.

A rare offering on the shores of Menemsha Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Thoughtfully designed with striking modern architecture, walls of glass, and seamless indoor-outdoor living, this one-of-a-kind compound captures breathtaking water views from nearly every room. Set on 4.9 acres with a private 115-foot deep-water dock, the property represents an irreplaceable opportunity, as a waterfront estate of this scale and caliber could no longer be replicated today. The main residence features six luxurious ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired bathrooms. Two state-of-the-art kitchens appointed with top-tier appliances provide exceptional spaces for entertaining, while the dramatic main living area showcases soaring cathedral ceilings and panoramic pond views. A screened porch and expansive waterfront deck create effortless transitions between interior and exterior living spaces. Upstairs, a striking glass-lined hallway with a dramatic glass floor overlooks the water, leading to guest suites with private baths and access to a second-floor deck. Exceptional amenities include a private theater with massage seating, wine cellar, outdoor shower, and a hilltop writer’s cottage with sweeping waterviews. Set just beyond the main house is the pool house. The pool house is a private wellness retreat featuring a heated indoor pool, spa, sauna, cold plunge, steam room, wet bar, and spacious enclosed porch surrounded by retractable glass doors. The second floor includes a full guest suite with a bedroom, living room, laundry, and dual balconies overlooking Menemsha pond. The estate also includes an impressive 1,927 sq. ft. barn-style entertainment pavilion designed to complement the property’s contemporary aesthetic while offering exceptional recreational amenities. The upper level features a professionally designed fitness center with floor-to-ceiling windows overlooking the grounds and pond, alongside a sprawling recreation lounge with space for indoor basketball, billiards, ping pong, and additional sporting activities. Below, the structure houses an expansive six-car garage, ideal for luxury vehicle storage, boating equipment, and recreational gear. Completing this incomparable estate are a private tennis court and charming boathouse by the dock for paddleboards and waterfront equipment. An unparalleled modern retreat in one of Martha’s Vineyard’s most exclusive waterfront settings.

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!

Rare Downtown Vineyard Haven Compound Offering! An exceptional opportunity to own two separate properties being offered together in the heart of Vineyard Haven. Just moments from the ferry terminal, restaurants, shops, and the harbor, this unique package offers the ideal blend of luxury living, investment potential, and an amenity that is nearly impossible to find in town with expansive parking. 33 Lagoon Pond Road is a newly constructed, thoughtfully designed three bedroom, three bathroom home where luxury meets sophisticated coastal charm. Featuring an open floor plan, a designer kitchen with quartz countertops, custom tile bathrooms, and seamless indoor-outdoor living, the home enjoys water views from the living room, bedrooms, and inviting front porch. A private backyard, spacious rear deck, and attached two car garage provide both privacy and convenience, while the property's impressive rental history adds outstanding investment appeal. Complementing the main residence is 29 Lagoon Pond Road, a beautifully renovated two bedroom, one bath cottage offering its own private retreat with a charming rear patio and outdoor shower. Ideal for extended family, guests, employee housing, or additional rental income, the cottage provides flexibility for a variety of ownership opportunities. A true standout feature of this offering is the oversized rear parking lot at 29 Lagoon Pond Road, accommodating approximately ten vehicles. Parking of this scale is exceptionally rare in downtown Vineyard Haven and significantly enhances the property's versatility. Whether you're seeking a family compound, an income producing investment, or a premier in town property with unmatched flexibility, 29 & 33 Lagoon Pond Road represent a truly one of a kind opportunity in downtown Vineyard Haven.

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!

Step into a piece of Martha's Vineyard history with this exceptionally charming antique Cape, originally dating back to 1808. While the home proudly retains its authentic historical character, boasting exquisite period details, rich moldings, and wide-pine floorboards, it has been thoughtfully updated to offer the ultimate in contemporary living. There are 5 total bedrooms: 2 on the first floor and 3 on the second floor. Two bedrooms are en suite: 1 on the 1st floor and 1 on the 2nd floor. There are 4 full bathrooms (3 renovated), and a light-filled, spacious kitchen, designed to blend old world charm with modern needs. Additional updates include central AC, 3 lined chimneys, and an upgraded septic system. A bluestone patio is ideal for al fresco dining, and a lovely, professionally maintained backyard and garden complete the storybook picture. Perfectly positioned across from picturesque Owen Park, this property places you at the very heart of Vineyard Haven culture and coastal convenience. Take in water views and boat activity on scenic Vineyard Haven Harbor. Enjoy the newly built town dock and the historic bandstand where you can enjoy the Vineyard Haven Band play on Sunday evenings in the summer. Schedule your tour today and experience the magic of Vineyard Haven living.

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.

Downtown Vineyard Haven with Harbor Views. Positioned between the energy of Main Street and the quiet prestige of West Chop, the 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. Mornings start with sunrise over the water, while evenings slow as the light fades across the shoreline. 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. 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.

Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within a reasonable distance from essential amenities and entertainment options. Whether you're looking for a year-round residence or a vacation getaway, this waterfront home in Squibnocket is an idyllic sanctuary to create unforgettable memories with family and friends.

Expanded cottage with in-law suite, garage, and detached studio. On the way to West Chop, it is equidistant to Downtown Vineyard Haven, the flagpole at West Chop, Mink Meadows Golf Club, and Vineyard Haven Yacht Club. This 4 bedroom, 4 bathroom property offers a flexible floor plan, including a private inlaw wing complete with its own entrance, kitchen, living room, full bathroom, and bedroom—perfect for extended family or guests. There are two driveways. The home also features a garage and a finished basement offering excellent storage or future expansion potential. A detached studio at the rear of the property provides wonderful overflow space for a home office, art studio, or guests. The property is only 2/10ths of a mile to the town beach at the end of Grove Ave, and half a mile to the town beach on Owen Little Way. Ready for a new owner's vision and updates, this well-located property presents an exceptional opportunity to enjoy the convenience and charm of this desirable neighborhood. This property is being offered "as-is."

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 in the highly sought-after Nora’s Meadow community in Edgartown, this exceptional coastal property offers the rare combination of privacy, acreage, and close proximity to downtown Edgartown, South Beach, and the Katama bike path. Set on 1.8 beautifully landscaped acres, this custom home was built in 2014 and features over 4,000 square feet of thoughtfully designed living space across three levels. A welcoming mudroom, ideal for beach living, opens into a bright and expansive main living area featuring a spacious dining room, gourmet kitchen, and comfortable living room with oversized French doors leading to the pool patio. The first floor primary suite offers a luxurious spa-inspired bath and private French doors opening to a serene outdoor sitting area surrounded by lush landscaping. Four additional guest bedrooms are all generously sized, providing ample accommodations for family and friends. The finished lower level includes a media room, pool table area, and abundant storage space. Designed for effortless indoor-outdoor living, the backyard is a true Vineyard retreat featuring an oversized pool, outdoor kitchen, expansive stone patio, and a pool cabana complete with a full bath. A two-car garage includes unfinished space above with the unique potential to create a guest house, an exclusive feature permitted only for this property within the Nora’s Meadow association. A charming barn-style shed provides additional storage for kayaks, bikes, and boating equipment. This rare offering combines luxury, privacy, and exceptional outdoor living in one of Edgartown’s most desirable neighborhoods, creating the ultimate Martha’s Vineyard retreat for generations to enjoy.

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest of its kind on Martha’s Vineyard. Originally built in 1835 and masterfully renovated by renowned architect Patrick Ahearn, the estate seamlessly blends historic character with refined modern luxury. Just moments from Edgartown Harbor and the island’s premier dining and shopping, the property spans two lots and offers an extraordinary compound featuring 10 bedrooms and 14 baths. Designed for both elegant entertaining and comfortable everyday living, the main residence showcases refined architectural details and modern technology. Beautiful oak floors run throughout the home, complemented by sophisticated hardware, premium appliances, and walls tastefully finished with nickel board. A gracious living room with fireplace opens to a patio with retractable screens, creating effortless indoor-outdoor flow. The chef’s kitchen is impeccably appointed with dual dishwashers, a plumbed miele coffee bar, refrigerator drawers, and a wine refrigerator. A custom brass and glass bar is equipped with an ice maker and refrigerated drawers and can easily be converted into a secondary kitchen. Two private bedrooms with en-suite tile baths anchor opposite wings of the main level, providing both privacy and balance. The main floor also includes an inviting secondary living room with a gas fireplace, an elegant dining room wrapped in seagrass wallpaper, a generous walk-in pantry, and a spacious mudroom thoughtfully designed for effortless island living. Upstairs a spectacular primary suite serves as a retreat, complete with private balcony and a bonus two full spa-inspired baths. Three additional en-suite guest rooms and a spacious laundry room complete the second floor. The third level features a charming nautical-themed bunk room with four built-in beds and full bath. The finished lower level includes two bedrooms with en-suite baths, a media room, wine cellar, and additional laundry. Beyond the main house is a beautifully finished two-car garage with brick floors and wood-paneled walls. The carriage house above the garage offers a private guest suite with a balcony overlooking the pool. The outdoor setting is unparalleled for in-town living. Lush hydrangeas surround a resort-style pool and spa, complemented by a built-in grill, firepit, and an exceptional cabana with kitchenette, half bath, laundry, heating and air conditioning. This Edgartown estate offers privacy, scale, and sophistication rarely found within steps of Main Street. An iconic Martha’s Vineyard property reimagined for modern coastal living.

Introducing a landmark property in Edgartown’s Starbuck Neck enclave, just one tenth of a mile to Fuller Street Beach. Included in this sale is an adjoining vacant buildable lot. 14 STARBUCK NECK features a 7-bedroom house with 5 full bathrooms, garage, and plunge pool. Known as the Tower House, this home offers delightful views of the harbor from the first and second floors. The views from the bedroom and office located in the tower are stunning. 23 THAYER STREET is an extremely rare vacant lot in the heart of the Starbuck Neck neighborhood. With well over a third of an acre of land, the lot will comfortably accommodate a 5-bedroom house with guesthouse and pool.

Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature’s grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home’s timeless architecture and expansive front lawn make an unforgettable first impression. Inside, the home features a bright and airy open-concept layout that seamlessly blends the living, dining, and kitchen areas, all enhanced by the dramatic “big sky, big water” setting. Spanning three levels, the residence offers 4 bedrooms, 3 full bathrooms, and a spacious family room. Nearly every room captures breathtaking water views, creating a true connection to the surrounding coastal landscape. Step outside to the backyard lawn and follow the wooden boardwalk to your own private sandy beach. Whether launching a kayak or paddleboard for a day exploring Katama Bay, or taking a scenic shortcut to South Beach, this waterfront setting offers the very best of Vineyard living. Completing the property is a generous 2-car garage

Awaken to sweeping, unobstructed views of Nantucket Sound from this meticulously crafted new build in Falmouth. Custom-designed for the discerning Cape Cod buyer. Serving as your private gateway to the quintessential Cape lifestyle, this exceptional property places you moments away from renowned local shores and an association beach option. Here, your days unfold effortlessly across a birding paradise perfect for windsurfing, swimming, and sun-drenched lounging, or exploring the nearby Shining Sea Scenic Bikeway. Ideal for avid boaters and nature enthusiasts alike, the location offers seamless access to nearby harbors and marinas, complemented by daily sightings of native coastal birds, wildlife and serene spaces for your garden. Equipped with modern conveniences including a garage that lives like an organized haven keeping everything at an arm's reach, an EV charger and a whole-house generator, every thoughtful detail ensures absolute peace of mind, creating an extraordinary sanctuary where coastal adventure and timeless memories await. The immediate area provides a long list of places to experience. Spohr Gardens is a breathtaking 6-acre woodland garden that can be easily accessed near the property. Spohr Gardens features a succession of seasonal blooms including thousands of daffodils, daylilies, rhododendrons, and azaleas, all set along paths with sweeping views of Oyster Pond and Nantucket Sound. Additionally, these winding trails are uniquely integrated with whimsical nautical artifacts, vintage lanterns, large millstones, and old ship anchors. Just a little further away some of the other areas include. The Knob is a scenic coastal nature area with narrow paths winding through a wooded peninsula to panoramic waterfront vistas. Oyster Pond Environmental Trust manages serene, low-impact passive paths through protected marshlands and coastal pond habitats. Beebe Woods is an expansive 383-acre forest featuring an extensive network of shaded dirt paths and carriage roads winding around scenic ponds and rolling hills. Two Ponds Conservation Area provides quiet dirt and boardwalk paths that loop through tranquil woodlands and wetland environments. Coonamessett Greenway Heritage Trail is a scenic pathway following the river corridor through cedar swamps, pine forests, and open fields.

A compelling opportunity to own in one of Falmouth's most desirable coastal locations. Welcome to 205 Grand Avenue, where the best of Cape Cod living is right outside your door. Ideally positioned in sought-after Falmouth Heights, this distinctive property offers the location buyers dream about—close to the beach, harbor, restaurants, and all the energy of Falmouth's vibrant seaside community. Enjoy morning walks along the shore, afternoons at the beach, and summer evenings taking in everything this iconic neighborhood has to offer. Whether envisioned as a year-round residence, Cape Cod retreat, or investment opportunity, 205 Grand Avenue offers exceptional versatility in a location that is increasingly difficult to replicate. Now offered at $2,400,000, this significant price adjustment creates a fresh opportunity for buyers who have been waiting for the right Falmouth Heights property. Come take another look—the value and possibilities may surprise you.

Spectacular water views from nearly every room! Breathtaking sunrises and sunsets overlooking Vineyard Sound, Bristol and Falmouth Heights Beaches, and Little Pond. This home offers one of the finest vantage points in town for enjoying the Fourth of July fireworks. Offered for the first time in over 100 years, this exceptional property combines timeless character with comfortable living. Rebuilt in 1992, two properties were combined and the structure was raised 14 ft., providing for a garage and basement. The convenience of one floor living is provided with an elevator, first-floor bedroom suite, and first floor laundry. Multiple living spaces are provided for entertaining family and friends. The sun-filled sunroom is the perfect place to start your morning. Additional features include a two-car garage, wrap-around deck, and a private yard ideal for summer enjoyment. Mechanicals on first and second floors. New 2000-gallon septic tank installed in 2026. Passing Title V in hand.

Tucked along the water's edge in one of Mashpee's most scenic settings, this rare coastal retreat offers the quintessential Cape Cod boating lifestyle with a private sandy beach area, deepwater dock and sweeping water views. Comprised of two waterfront parcels at 22 & 23 Samoset Road, the property blends the charm of a classic Cape retreat with exceptional potential to renovate, reimagine or enjoy as-is. The light-filled interior features vaulted ceilings with exposed beams, wide pine floors and walls of glass framing the water beyond. An expansive waterfront deck creates seamless indoor-outdoor living, while the spacious living room with dramatic brick hearth and wood stove flows to the dining area, kitchen and water-facing gathering spaces. The adjoining waterfront parcel provides added privacy and exciting possibilities for expanded outdoor living or other future improvements, subject to applicable approvals. With conservation land beyond, sandy frontage, deepwater access and remarkable potential, this is a truly special opportunity to own a legacy Cape Cod waterfront property. Credit being provided for new septic & roof.