268 houses for sale in Chappaquiddick

NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed home by Morgan Studio, a husband-and-wife-led boutique design firm. Created for effortless indoor-outdoor living, the residence features soaring ceilings, a flowing floor plan, oversized windows, and exceptional materials and finishes throughout. A private interior courtyard, envisioned as an edible garden, anchors the home and connects seamlessly to the cathedral-ceiling great room with a wood-burning fireplace and a 20' x 40' heated gunite pool. The chef's kitchen features a Patagonia Tiffany stone island, breakfast nook, and butler's pantry. Private bedroom suites occupy separate wings, including a spa-inspired primary suite with a circular skylit shower and wall-to-wall travertine. A bright lower level with 10-foot ceilings provides generous recreation and entertaining space. A custom furniture package is available upon request for a truly turnkey offering. Conveniently located near Crocker Drive with e

A RARE KATAMA JEWEL BOX - TURNKEY LUXURY TODAY, WITH ROOM TO GROW. In one of Edgartown's most coveted enclaves, this beautifully reimagined three-bedroom, two-bath residence offers the ease of new construction with timeless Vineyard character. Taken down to the frame and rebuilt in 2024 by a hand-picked team of the Island's finest builders and craftsmen, the home is essentially brand new - every system, every surface, every finish. And with room to expand to as many as six bedrooms*, it's a turnkey retreat today and a signature compound tomorrow. The home lives far larger than its footprint. Vaulted ceilings open the great room to the rafters, crowned by reclaimed beams milled from an 1800s Ohio barn and anchored by a classic brick fireplace. Wide-plank floors run throughout. Behind the new walls and vaulted ceilings: new spray foam insulation, all-new plumbing and electrical, and energy-efficient mini-splits for quiet heating and air conditioning. The designer open and vaulted kitchen

NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed home by Morgan Studio, a husband-and-wife-led boutique design firm. Created for effortless indoor-outdoor living, the residence features soaring ceilings, a flowing floor plan, oversized windows, and exceptional materials and finishes throughout. A private interior courtyard, envisioned as an edible garden, anchors the home and connects seamlessly to the cathedral-ceiling great room with a wood-burning fireplace and a 20' x 40' heated gunite pool. The chef's kitchen features a Patagonia Tiffany stone island, breakfast nook, and butler's pantry. Private bedroom suites occupy separate wings, including a spa-inspired primary suite with a circular skylit shower and wall-to-wall travertine. A bright lower level with 10-foot ceilings provides generous recreation and entertaining space. A custom furniture package is available upon request for a truly turnkey offering. Conveniently located near Crocker Drive with e

A RARE KATAMA JEWEL BOX - TURNKEY LUXURY TODAY, WITH ROOM TO GROW. In one of Edgartown's most coveted enclaves, this beautifully reimagined three-bedroom, two-bath residence offers the ease of new construction with timeless Vineyard character. Taken down to the frame and rebuilt in 2024 by a hand-picked team of the Island's finest builders and craftsmen, the home is essentially brand new - every system, every surface, every finish. And with room to expand to as many as six bedrooms*, it's a turnkey retreat today and a signature compound tomorrow. The home lives far larger than its footprint. Vaulted ceilings open the great room to the rafters, crowned by reclaimed beams milled from an 1800s Ohio barn and anchored by a classic brick fireplace. Wide-plank floors run throughout. Behind the new walls and vaulted ceilings: new spray foam insulation, all-new plumbing and electrical, and energy-efficient mini-splits for quiet heating and air conditioning. The designer open and vaulted kitchen

COMMANDING WATER VIEWS ON CHAPPAQUIDDICK - This beloved fishing cottage rests high above one of the premier fishing areas on the island of Chappaquiddick. Set apart from the hustle and bustle of downtown, but within easy reach of all Edgartown offers, the pristine views over the wilds of Cape Pogue and the outer harbor bring peace and serenity for all who visit. Fishing, clamming, swimming, sailing, and relaxing with friends or family are just a few of the daily dalliances of time spent on Chappy. There is simply no better place to relax and unwind

Life on Chappaquiddick has a rhythm all its own - and this exceptional compound is designed to savor every moment of it.Set on three park-like acres of meadows and woodland, two freshly painted log cabin-style homes offer a private world apart. The three-bedroom main house is open and generous, with living spaces that flow seamlessly from inside to out. The two-bedroom guest house is its own considered retreat, complete with covered porch, back deck, and outdoor shower. An oversized garage with loft provides additional space to gather and unwind.A circular drive and pea stone pathways connect the buildings across beautifully layered grounds. Adirondack chairs ring a custom firepit for late nights under the stars; a sauna and cold plunge pool on a bluestone patio create your own personal spa. An enclosed garden, garden shed, and multiple outbuildings complete the setting - your own private park among Martha's Vineyard most beautiful natural setting

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 proper

Located on a quiet street just moments from Edgartown Village, this versatile compound offers a rare combination of privacy, flexibility, and proximity to some of the Island's most treasured outdoor amenities. Set on over a half-acre, the property features a main residence and a detached guest house, thoughtfully positioned with separate driveways and a natural buffer of mature trees. The main house offers a comfortable and inviting interior, highlighted by a bay window and a spacious open kitchen and dining area with granite countertops, custom cabinetry, and direct access to the deck. A sunken living room offers separation while maintaining an open flow. The main level includes a primary bedroom and an additional bedroom, while the second floor offers a third bedroom, a full bathroom, and flexible living space. The finished lower level offers approximately 790 sq ft of additional finished space, including a recreation area, den, and full bathroom, along with approximately 525 sq ft o

This traditionally styled residence offers exceptional quality and craftsmanship in a coveted Edgartown location, situated on a corner lot just blocks from downtown and the harborfront. Thoughtfully designed for both elegant entertaining and relaxed island living, the home features beautifully proportioned interiors that flow seamlessly from one space to the next. The inviting front foyer opens to a gracious living room with fireplace and French doors leading to a deep, covered porch complete with its own fireplace. The 1st floor continues to a private den with fireplace, while the dining room and spacious kitchen/family room complete the main living spaces. Abundant windows and French doors throughout the 1st floor provide an effortless connection to the covered porch and the beautifully landscaped grounds. The 2nd floor offers 4 well-appointed bedrooms and 3 full baths providing comfortable accommodations, with most bedrooms offering access to private 2nd-floor decks. The finished lo

Hidden Cove Gem with Serene Pond Views And Coveted Water Access - Located in the desirable Hidden Cove enclave-a 65+ acre water-access community-this inviting contemporary home offers privacy and high-end finishes with direct access to Sengekontacket Pond and Nantucket Sound. Community amenities include a private boat dock, walking trails, pickleball and tennis, all near Oak Bluffs. The sun-filled interior features a living room with vaulted ceilings, a wood-burning fireplace, and floor-to-ceiling windows. The chef's kitchen is appointed with stone countertops and Dacor(R) appliances. The second-floor primary suite boasts a private balcony with pond views and a stylish en suite bath. The garden level provides additional bedrooms and a bonus space with a Murphy bed. Outside, enjoy a bluestone terrace and two levels of decks overlooking a private yard. This move-in-ready home is offered fully furnished with over $80,000 in 2026 summer rental income already secured

Ideally situated between South Beach and Edgartown Village, this newly renovated Katama compound offers exceptional flexibility for personal use and rental income.The four-bedroom contemporary main house features a newly constructed, expansive great room with a cathedral ceiling and an abundance of windows that fill the space with natural light. The open floor plan flows from the updated kitchen into a living room centered around a classic brick fireplace. Skylights bring in additional sunlight, while sliding doors open to expansive new south-facing decks-perfect for outdoor dining, entertaining, and relaxing after a day at the beach. The third floor provides a second living area, bedroom, and private half bath. A full basement offers ample storage and potential for additional finished living space. The detached two-car garage includes a private one-bedroom apartment above with its own wraparound deck. A bonus room with a half bath on the garage's main level is ideal for an office. A c

Set in a private community, Sweetened Water Farm offers the pastoral charm of Martha's Vineyard's rural up-island, just minutes from the energy of downtown Edgartown. Residents share access to the association's horse barn and common pastures, ideal for keeping horses or other livestock, adding to the farm's authentic agrarian character. This custom-built home is a true Vineyard gem, crafted over time by local artisans and set against sweeping pastoral views. The main house currently offers 3 bedrooms and 2 bathrooms, with the potential to expand to 6 bedrooms, as approved by the Edgartown Board of Health and Building Department. Inside, the home tells its own story: African mahogany millwork in the library, massive fieldstone fireplaces, and a Jotul wood stove. Built to the same exacting standard, the barn and garage include a custom wood-fired sauna and a two-room office on the second floor

Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an expansive screened porch - ideal for entertaining on warm summer evenings. A welcoming front porch provides additional outdoor living space. The main level is completed by a gracious primary suite with a full bath and a convenient half bath. The walk-out lower level features two additional bedrooms, a full bath, and laundry. A one-car garage offers excellent storage for your car, kayaks, or beach gear. Perfectly positioned between Edgartown and Oak Bluffs. Additional bedrooms possible with septic upgrade per BOH

Privately nestled amid sweeping gardens and lush natural landscaping, this 3-bedroom, 3-bath home offers the perfect blend of timeless design and refined contemporary living. Thoughtfully curated interiors feature an open-concept living area, a large kitchen with Viking cooktop, Fisher and Paykel dishwasher and quartz countertops, inviting dining spaces, and comfortable gathering rooms filled with natural light. French doors open to a brick patio with fireplace, surrounded by mature gardens, creating seamless indoor-outdoor living ideal for entertaining or quiet relaxation. With beautifully designed indoor and outdoor spaces in the heart of Katama, this property is a true Vineyard sanctuary

Privately nestled amid sweeping gardens and lush natural landscaping, this 3-bedroom, 3-bath home offers the perfect blend of timeless design and refined contemporary living. Thoughtfully curated interiors feature an open-concept living area, a large kitchen with Viking cooktop, Fisher and Paykel dishwasher and quartz countertops, inviting dining spaces, and comfortable gathering rooms filled with natural light. French doors open to a brick patio with fireplace, surrounded by mature gardens, creating seamless indoor-outdoor living ideal for entertaining or quiet relaxation. With beautifully designed indoor and outdoor spaces in the heart of Katama, this property is a true Vineyard sanctuary

Located on nearly 2-acres in the exclusive and newly created Trapps Pond Preserve, is this grand luxuriously appointed home. This is one of four homes being built and will be the first to be completed. Every room in the house is on a scale not often afforded in a Vineyard home, with 10 ft coffered ceilings and open/flowing floor plan. There is an abundance of light streaming in from the oversized windows, wonderful craftsmanship throughout and the home that offers 7 bedrooms, all with private baths. The 2-story living room features a massive stone fireplace, balconies that look down from the second floor and a grand 20 ft. diameter circular staircase. There is a huge gourmet kitchen, dining room, lower-level gym, media room and recreation area, are nicely arranged on the over 8,000 sq. ft. of living space. There is a large parking courtyard, a 3-car garage and swimming pool, all amidst a lush backdrop of manicured landscaping and mature perimeter vegetation. This incredible newly offer

Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane offers a rare opportunity to own a stunning 3.7 acres in one of Martha's Vineyard's most exclusive communities. The property enjoys picturesque views over the 7th fairway and 8th tee box, across to Sengekontacket Pond, creating a peaceful backdrop of lush greens and distant water. The historic five-bedroom main residence, along with a separate one-bedroom carriage house, are rich in character and await a thoughtful renovation or reimagining. Ideally located near the clubhouse, restaurant, tennis courts, and pro shop, the property offers easy access to the Farm Neck lifestyle while remaining just minutes from town, the harbor, and ferry terminal. This is an extraordinary chance to secure a property within the esteemed Farm Neck Golf Club community. Included is a highly sought-after Farm Neck Club Stockholder Membership, enhancing both its prestige and value

Set within the coveted Meadow View Farms community, this exceptional post-and-beam residence offers timeless craftsmanship, generous living spaces, and nearly an acre of private beautifully landscaped grounds with significant potential for expansion. A full-length farmer's porch creates a gracious arrival and provides the perfect setting to relax. Inside, the sun-drenched main level is defined by soaring cathedral ceilings, rich hardwood floors, and a striking hand-cut stone propane fireplace that anchors the open-concept living spaces. The well-appointed kitchen with casual dining area flows seamlessly into a formal dining room and an inviting living room, creating an ideal layout for both everyday living and entertaining. A spacious mudroom offers practicality and convenience after beach days or inclement weather. The primary suite is privately situated on the first floor and features abundant natural light from a bay window overlooking the backyard, a walk-in closet, and an oversize

Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor shower, parking, and mini-split climate control; its upstairs bedroom enjoys views from Farm Pond to Nantucket Sound. Completing the property is the charming Lilac House, a fun open-concept bunk house with a full bath, water-view deck, and private outdoor shower. A wraparound porch captures sweeping ocean views, while beaches, shops, restaurants, Circuit Avenue, and the Harbor are moments away. An established rental history further enhances this rare opportunity in one of Oak Bluffs' most iconic locations

Located in the heart of downtown Oak Bluffs, this charming updated home seamlessly blends classic Vineyard character with bright, modern comfort. Greeting you from the street is an expansive wraparound porch framed by vibrant hydrangeas and a cozy second-floor balcony. Step inside to an inviting open layout featuring crisp white paneled walls, exposed painted ceiling beams, and warm hardwood floors that create an airy, light-filled atmosphere. Designed for relaxed coastal living, this partially insulated retreat offers effortless indoor-outdoor flow and functional updates throughout. Enjoy an unbeatable location directly across the street from the neighborhood playgroud and just a short, scenic walk to pristine beaches, local dining, and the ferry terminal. Whether you are seeking a summer sanctuary or an investment property, this home delivers classic island living at its best! Showings on Saturdays 1-3pm only beginning August 1

Located in the heart of downtown Oak Bluffs, this charming updated home seamlessly blends classic Vineyard character with bright, modern comfort. Greeting you from the street is an expansive wraparound porch framed by vibrant hydrangeas and a cozy second-floor balcony. Step inside to an inviting open layout featuring crisp white paneled walls, exposed painted ceiling beams, and warm hardwood floors that create an airy, light-filled atmosphere. Designed for relaxed coastal living, this partially insulated retreat offers effortless indoor-outdoor flow and functional updates throughout. Enjoy an unbeatable location directly across the street from the neighborhood playgroud and just a short, scenic walk to pristine beaches, local dining, and the ferry terminal. Whether you are seeking a summer sanctuary or an investment property, this home delivers classic island living at its best! Showings on Saturdays 1-3pm only beginning August 1

This exceptional mixed-use property occupies a premier location in the heart of Oak Bluffs thriving Circuit Avenue business district. Meticulously renovated and designed by architect Chuck Sullivan, the building offers a distinctive combination of commercial and residential spaces in one of Martha's Vineyard's most sought-after high-foot-traffic downtown locations. The Union Chapel, across the street, and the Tabernacle, behind the property, host major Island events. Every aspect of the property reflects an outstanding level of craftsmanship and attention to detail. The street level features an expansive commercial space with considerable flexibility for restaurant-bar and/or retail use (for a restauranteur, the kitchen and bar infrastructure are intact and virtually turnkey). The commercial floor includes three handicap-accessible half baths and a convenient and thoughtfully designed rear exterior loading area. The very large newly excavated basement is dry and temperate year-round, p

Beach Farm is an extraordinary 18.6-acre waterfront estate offering exceptional privacy, 1,700 feet of water frontage, sweeping Atlantic views, private beaches, a rare walking path to the pristine South Shore, and a short bike ride to Edgartown Village. The estate is set within the storied 200-acre Herring Creek Farm, a coastal enclave surrounding a working farm with barns, horses, sheep, and open meadows. Bordering both the 900-acre Edgartown Great Pond and the Atlantic Ocean, Beach Farm includes a six-bedroom main residence completed in 2023 with expansive walls of glass that frame dramatic, panoramic views across the pond and ocean. Built to the highest standards by master craftsmen, the home is complemented by a three bedroom surf house with outdoor sauna, cold plunge, a workout barn, private walking trails, and secluded beaches

Directly Across from Inkwell Beach, this Victorian Queen has stood the test of time. Partially insulated to extend the season, the new kitchen and bath are cozy in winter and open and bright in summer. 5 bedrooms, 1.5 baths with an outdoor shower, there's plenty of room for family and friends. The front porch has been a gathering place for 50+ years, and the views have not been expanded. So much opportunity; this house is being sold As-Is

Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living areas. Upstairs are two additional bedroom suites, a loft-style family room/office, dedicated laundry, and flexible bonus room ideal for guests, media, or recreation. A screened porch, covered outdoor living spaces, and attached two-car garage enhance both functionality and lifestyle. Built with high-end finishes and attention to detail throughout, this stunning new construction offering presents an opportunity to own a luxury retreat with easy access to Oak Bluffs' beaches, harbor, restaurants, shops, and all the attractions that make the Vineyard such a sought-after destination

Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living areas. Upstairs are two additional bedroom suites, a loft-style family room/office, dedicated laundry, and flexible bonus room ideal for guests, media, or recreation. A screened porch, covered outdoor living spaces, and attached two-car garage enhance both functionality and lifestyle. Built with high-end finishes and attention to detail throughout, this stunning new construction offering presents an opportunity to own a luxury retreat with easy access to Oak Bluffs' beaches, harbor, restaurants, shops, and all the attractions that make the Vineyard such a sought-after destination

Experience the timeless beauty of Martha's Vineyard from this luxurious waterfront retreat where the landscape feels so effortlessly connected to daily life. This property embodies understated luxury and timeless design, featuring a meticulously crafted stone residence and guest house. The setting overlooking Edgartown Great Pond has a sandy pond beach and deeded access to the pristine Atlantic Ocean Beach. Ospreys and redtail hawks soar overhead in this naturalized setting that is only 13 minutes to Edgartown village or the MV airport, yet a world away. This is a rare combination of privacy and proximity. An opportunity to own one of the Vineyard's most distinctive properties. The home was thoughtfully designed to embrace its exceptional surroundings; the residence is filled with natural light and enjoys beautiful water views. Custom floor to ceiling sliding doors invite the outside in. Spacious interiors flow easily to inviting outdoor living spaces, enhanced by a swimming pool, walk

Incredible opportunity for workforce housing, live in one/rent the other, or multi generational family living. Main house has 4 levels of living space. Main floor living/kitchen/dining/full bath and laundry. 2nd floor has two bedrooms and full bath. 3rd floor is a large finished bonus room. The full walkout basement in the main house is finished with private entry, full bath, separate rooms and laundry. The guest house was completely renovated top to bottom in 2023, new everything! Included but not limited to: new kitchen, baths, windows, roof, siding, electrical and plumbing. Landscape around guest house has new stone walls, patio, and pea stone driveway. Guest house is 1 bedroom, 1.5 bath and really is a gem. Main house has been fully rented year-round for years and may need a little TLC for the next owner, a new asphalt roof on main house was installed in 2025. Guest house has been rented via airbnb and has all 5 star reviews. A new septic system was installed in 2018. This property

Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside from boating, the swimming and clamming in the immediate waters are sublime. Expansive lawns slope down to the water on three sides of the residence - one of the most enchanting settings on the waterfront on Martha's Vineyard

Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside from boating, the swimming and clamming in the immediate waters are sublime. Expansive lawns slope down to the water on three sides of the residence - one of the most enchanting settings on the waterfront on Martha's Vineyard