luxury house for sale Tisbury, United States

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.

This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a 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 rear deck for an eat-in or eat-out option. With separate finished living quarters on the garden level, the home easily accommodates guests, or multi-generational living. The expansive deck invites morning coffee, summer gatherings, and peaceful evenings surrounded by nature. Mature plantings bloom on stone-scaped retaining walls and evergreen trees provide ultimate privacy. You are just moments from the harbor, shops, and ferry, and yet this property also offers seclusion and privacy - this is a rare combination in this price point.

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.

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.

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.

Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower, perfect after a day at the beach. Also on this level is a comfortable guest bedroom with peaks of the harbor, a stylish full tile bath with a glass-enclosed shower, a cozy living area, and washer/dryer for convenience. Upstairs, cathedral ceilings and a gas fireplace create an inviting open-concept living space. The gourmet kitchen is outfitted with sleek Bosch appliances, a large center island ideal for entertaining, and an adjoining dining area. Enjoy panoramic water views of the harbor, passing ferry boats, and Vineyard Sound from the entire second floor, or step out onto your private deck, perfect for alfresco dining or morning coffee. Just steps from your door, a private path leads to the association’s sandy harbor beach where you can store your kayak or launch your boat. This condo also includes a dedicated parking space and an enclosed storage area under the house ideal for bikes, beach gear, or seasonal items. With easy access to downtown shops, restaurants, ferry terminal, and local beaches, this condo offers the ultimate combination of luxury, convenience, and island charm. A rare opportunity for carefree coastal living on Martha’s Vineyard.

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.

Tucked back from the road on scenic Lake Street, this one-of-a-kind home offers privacy and charm on a beautifully landscaped 0.7 acre lot accented by mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm and inviting atmosphere. The home’s four-level design provides exceptional character and flexibility. The main level features a spacious kitchen with a center island that opens to a dining area. A sunken living room with floor-to-ceiling windows overlooks the surrounding tree canopy, filling the space with natural light. Just off the living room, a large screened porch offers a peaceful setting for relaxing outdoors. Two bedrooms, a full bath, and a laundry room complete this floor. Up the wood staircase, the second level includes a dramatic hallway that overlooks the living area below and leads to a generous primary suite with a spacious bathroom and additional laundry. The third level features a private guest bedroom with its own living area and full bath, ideal for visitors or extended stays. The finished lower level adds even more living space, offering a full bathroom, bedroom windows, and a walkout door to the side yard. A spacious garage provides added convenience and storage. Convenient to the public boat landing on Lake Tashmoo and the Lake Street tennis and pickleball courts, and just a short distance to Downtown, this is the ideal Vineyard Haven location.

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.

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!

Ideally located just minutes from the heart of Vineyard Haven, 21 Davis Street offers exceptional island living in this beautifully crafted five-bedroom, four-bathroom home with 3,704 square feet of thoughtfully designed living space. Rich hardwood flooring, custom cabinetry, elegant Restoration Hardware vanities, and custom tilework throughout the bathrooms reflect the care and craftsmanship the homeowner has poured into every detail. The grounds are equally impressive, featuring beautiful stonework, handcrafted bluestone patios, and professionally landscaped outdoor spaces designed for effortless entertaining. Enjoy summer evenings by the outdoor fireplace, unwind in the Jacuzzi, or rinse off after the beach in the private outdoor shower, all creating a true Vineyard lifestyle experience. Lovingly maintained and thoughtfully designed, this property offers both comfort and refinement just moments from Vineyard Haven Harbor, the ferry, shops, restaurants, and the island’s renowned beaches.

COMING SOON! Welcome to 18 Sylvan Avenue, a delightful, custom-crafted four-bedroom, four-bath, contemporary-style home set at the end of a quiet neighborhood road in Vineyard Haven. Surrounded by eight acres of conservation land, the property offers a peaceful setting with a spacious wraparound deck overlooking the natural landscape. It truly feels like its own private enclave, both inside and out. The home is in pristine, move-in-ready condition and has been thoughtfully renovated and meticulously maintained by the current owners. A welcoming entry leads directly into the open-concept space where a well appointed living room with fireplace flows into the dining area and kitchen. Positioned to the right of the entry is the primary bedroom suite, while two additional bedrooms and two bathrooms are tucked beyond the kitchen on the opposite side of the home, creating a functional and well designed layout which maximizes privacy. A finished lower level with a full bathroom and laundry provides additional flexible living space or a fourth bedroom. Skylights and sliders throughout the home fill the interior with natural light and create an easy connection to the multiple decks, beautiful mature gardens and woodlands. With an impressive rental history, this unique property is offered turnkey, making it an ideal opportunity as a year-round residence, Island retreat, or investment property. A true gem, conveniently located only 1.5 miles to Vineyard Haven’s Main Street shops, restaurants and ferry terminal, and only 5 miles to all that downtown Oak Bluffs has to offer! Showings begin on September 25th.

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.

3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! Discover 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 solarium or sunroom, 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 lot, the site is large enough to support a 4-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, two decks for outdoor enjoyment, a vintage garden shed, and a full dry basement for additional storage.

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.

RECENTLY COMPLETED and in a league of its own in Falmouth Heights. Nothing to renovate. Nothing to compromise. Everything to love about this exceptional water-view home, just steps from Falmouth Harbor and Falmouth Heights Beach. Pristine and thoughtfully renovated, this three-bedroom, two-and-a-half-bath residence blends timeless Cape Cod character with exceptional craftsmanship and sophisticated finishes. Wide-plank, 6.5-inch French oak hardwood flooring flows throughout, while the beautifully designed kitchen features leathered quartz countertops, a custom farmhouse sink, and custom cabinetry with convenient pull-out shelving. The buyer will also have the opportunity to select the LG refrigerator configuration that best suits their preferences. After a day at the beach, rinse off in the inviting outdoor shower, gather around the gas fireplace, or unwind during a relaxed summer evening in one of Falmouth Heights' most desirable neighborhoods. Additional amenities include oil heat, air conditioning, and underground irrigation. Park the car and enjoy everything the neighborhood has to offer on foot. Stroll to Falmouth Heights Beach, the harbor, Shipwrecked, the Falmouth Yacht Club the Black Dog Tavern, the Kite Flying Field, Grand Avenue, and Bristol Beach. Walk to the Island Queen for a day trip to Martha's Vineyard—or simply stay home and savor the water view. Ideal as a year-round residence, a refined Cape retreat, or an investment with attractive rental potential, this property offers a rare combination of pristine condition, an exceptional renovation, and an unforgettable location. Recently completed. Impeccably finished. Simply arrive and enjoy Falmouth Heights. The property is located in an AE flood zone. Buyers should independently verify flood-insurance requirements, rental regulations, and all property information.

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.

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.

Rarely does a property offer the privacy of 2.88 acres while being just a short stroll to downtown Falmouth and the beautiful surf drive beaches. This spacious 4-bedroom Cape is designed for comfortable year-round living and memorable gatherings. The inviting living room is centered around a wood-burning fireplace, while the eat-in kitchen features a convenient walk-in pantry for exceptional storage. Two bright sunrooms provide the perfect spaces to relax with a morning coffee, entertain guests, or simply enjoy views of the surrounding gardens and natural landscape. Step outside to the expansive wraparound elevated deck, where you'll overlook a peaceful yard that feels like your own private bird sanctuary. Mature gardens, two storage sheds, and abundant privacy create a truly tranquil setting. Additional features include a walk-out basement, one-car garage, whole-house generator, oil heat, and mini-split air conditioning for year-round comfort. Whether you're looking for a year-round residence or a Cape Cod getaway, this exceptional property offers the best of both worlds--peaceful seclusion with the convenience of being so close to Main Street and Surf drive beach.

Rare Woods Hole Village Opportunity with Eel Pond Views! Discover the timeless charm of this corner lot village property where coastal beauty meets everyday convenience. Enjoy morning coffee on the inviting porch as boats glide across Eel Pond, with cafés, acclaimed restaurants, Stony Beach, the Vineyard ferries, the Boston bus, MBL, WHOI, and the bike path all just steps away. Inside, period details shine through hardwood floors, tall ceilings, and original woodwork. The living room features handcrafted built-ins and a Jotul wood burning stove flowing into an adjacent dining area. The eat-in kitchen opens directly to the porch for effortless indoor-outdoor living with peaceful water views. Two bedrooms and a full bath complete the main level, while the second floor offers two additional bedrooms and another full bathroom. The walk-out lower level offers laundry, double entry doors, and wide-open space ideal for storing small boats and kayaks or potential future finished area. Mature landscaping, whimsical charm, privacy, and ample parking make this a truly special offering. All this, and just minutes to downtown Falmouth. Don't let this one pass you by!

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.

This remarkable 5+ acre waterfront estate is one of the most extraordinary coastal offerings to come to market in generations. Perched on the southwest tip of an exclusive community, it is Cape Cod's southernmost private residential land. The property commands panoramic, unobstructed views across Buzzards Bay to Naushon and the Elizabeth Islands, and then onto Vineyard Sound and Martha's Vineyard. The estate features more than 611 feet of shoreline, anchored by a substantial protective seawall that ensures both privacy and structural permanence, as well as a private, pristine sandy beach. A charming three-bedroom cottage currently rests on the grounds, offering immediate enjoyment while serving as an unparalleled canvas for a world-class waterfront masterpiece. Future development allows for a two-story residence designed to capture expanded views toward Great Harbor, subject to local approvals. This is more than a property - it is a private sanctuary where sea breezes, sunrises and dramatic sunsets define daily life. Representing an unrepeatable investment in New England's most authentic and unspoiled coastal landscape, it offers a level of prestige and natural beauty that is impossible to replicate. Breathtaking. Timeless. Truly Irreplaceable.

Coming Soon - Tucked within the desirable Greengate community, this 4-bedroom, 4-bath shingle-style home is designed for easy Cape Cod living and memorable gatherings. Set on nearly an acre of privacy, the property is wrapped in lush, mature plantings that create a sense of retreat the moment you arrive. At its heart lies the showpiece: a sparkling 50 foot gunite pool and expansive patio. This is where life slows and memories are made--sun drenched summer afternoons, dinners under the stars, and lively celebrations with family and friends. Inside, the inviting layout includes two first-floor bedrooms, open and comfortable living and dining areas, and seamless access to the pool and patio. Upstairs, two additional bedrooms offer space for family and visiting friends, while the partially finished lower level extends the possibilities--whether it's a game room, creative studio, or space for overflow guests. From this location, everyday living feels like a getaway. Bike the neighborhood Shining Sea Bikeway, explore the charm of Woods Hole, wander through vibrant downtown Falmouth, or catch a ferry to Martha's Vineyard on a whim--all just moments away. This is a home where outdoor living meets coastal lifestyle, a true oasis awaiting new owners to experience the best that Falmouth has to offer.