27 properties for sale in Chappaquiddick

Set amongst beautifully landscaped grounds and vibrant gardens, this inviting Chappaquiddick retreat offers a wonderful sense of privacy and tranquility. Stunning hydrangeas frame the property, also complemented by mature trees, colorful blooms, and established gardens, creating a beautiful setting throughout the seasons. Multiple outdoor spaces invite relaxing and entertaining, with a heated saltwater pool, completed in 2025, serving as the centerpiece. Inside, warm and inviting living spaces are filled with natural light, while shiplap details and a relaxed coastal aesthetic give the home a classic island feel. Vaulted ceilings and thoughtful attention to detail enhance the home's comfortable, refined character, while a thoughtfully designed single-level layout offers the ease and convenience of true first-floor living, with a private primary suite and separate guest wing providing an ideal sense of space and privacy. The detached studio with workshop is a hobbyist's dream, overlooki

This stunning custom-built waterfront estate offers sweeping views of Edgartown Harbor and exceptional craftsmanship throughout. Set on a private Chappaquiddick compound, the property features a beautifully designed main house, a separate one-bedroom guest house, a pool and spa, and expansive outdoor living spaces perfect for entertaining. Inside, warm wood finishes complement the home's comfortable scale, while the gourmet kitchen, spacious living room with a stone fireplace, and walls of windows showcase the spectacular harbor views. The second floor includes two queen suites, a bunkroom, and breathtaking water views from nearly every room. The finished lower level features a home theater and recreation room. A private path leads to the property's beach and deep-water dock, while a barn across the meadow offers a fitness center, guest suite, and basketball court. Cruise to Main Street Edgartown by skiff or take the nearby Chappy Ferry. This exceptional waterfront retreat offers the p

An exceptional offering in the heart of Edgartown Village, 14 Thayer Street presents the rare combination of estate-scale grounds, privacy, and an in-town location. Set across an extraordinary 0.62-acre double lot, the property unfolds as a private retreat just moments from the harbor, shops, galleries, and restaurants of downtown Edgartown. Expansive lawns, mature landscaping, and a substantial swimming pool create a setting more often associated with properties well beyond the Village center, offering remarkable space for outdoor living, entertaining, and generations of summer gatherings. At the heart of the property is a distinguished five-bedroom, five-bath residence encompassing more than 3,100 square feet. Rich in authentic Vineyard character, the home is attributed to Frederick Baylies Jr builder of Edgartown's iconic Old Whaling Church, lending architectural significance to an already exceptional property. Yet it is the combination of land, location, and lifestyle that truly di

Set amongst beautifully landscaped grounds and vibrant gardens, this inviting Chappaquiddick retreat offers a wonderful sense of privacy and tranquility. Stunning hydrangeas frame the property, also complemented by mature trees, colorful blooms, and established gardens, creating a beautiful setting throughout the seasons. Multiple outdoor spaces invite relaxing and entertaining, with a heated saltwater pool, completed in 2025, serving as the centerpiece. Inside, warm and inviting living spaces are filled with natural light, while shiplap details and a relaxed coastal aesthetic give the home a classic island feel. Vaulted ceilings and thoughtful attention to detail enhance the home's comfortable, refined character, while a thoughtfully designed single-level layout offers the ease and convenience of true first-floor living, with a private primary suite and separate guest wing providing an ideal sense of space and privacy. The detached studio with workshop is a hobbyist's dream, overlooki

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 22 at 131 N. Water Street is a beautifully appointed 960+/- sq. ft second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a microwave, and refrigerator/freezer. An in-unit washer/dryer, outdoor shower, and elevator access add everyday convenience. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, gas fire pits, and exceptional hospitality. A rare opportunity to own a luxury residence at one of Martha's Vineyard's most celebrated destinations. Harbor View Hotel retains a Right of First Refusal as outlined in the Master

Edgartown Village Compound with Harbor Views: Positioned in the heart of Edgartown's historic district, 114 North Water Street is a newly complete, move-in-ready property offering views of Edgartown Harbor. The offering includes eight bedrooms and seven-and-a-half baths across three thoughtfully designed structures: a six-bedroom, five-and-a-half bath main residence, a one-bedroom guest house with full kitchen, and a two-car carriage house with additional living quarters. The property features a private backyard oasis with a 16' x 32' saltwater pool, spa, and pool cabana-an exceptional outdoor setting in Edgartown Village. With furnishings and window treatments included, the home is ready for immediate enjoyment. 114 North Water Street represents a turnkey Edgartown Village estate offering the scale, amenities, and setting that are seldom available in this iconic location

This classic Edgartown Colonial is ideally situated in the heart of the village, just a short stroll from Fuller Street Beach, as well as Edgartown's acclaimed restaurants, boutiques, and harbor. Designed for comfortable coastal living and effortless entertaining, the open-concept floor plan flows seamlessly throughout the home. Offering 10 well-appointed rooms, the residence features six bedrooms, four full bathrooms, and two powder rooms. The gourmet kitchen opens to the spacious living and dining areas, creating an inviting gathering space that extends through French doors to a generous bluestone patio. The beautifully landscaped yard is highlighted by a private, thoughtfully sited swimming pool, providing a peaceful outdoor retreat perfect for relaxing or entertaining

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 62 at 131 N. Water Street is a beautifully appointed 865+/- sq. ft second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cook-top stove, microwave, and refrigerator/freezer. An outdoor shower adds to everyday convenience. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Harbor View Hotel retains a Right of First Refusal as outlined in the Master Deed. Washer/Dryer and dedicated stora

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 22 at 131 N. Water Street is a beautifully appointed 960+/- sq. ft second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a microwave, and refrigerator/freezer. An in-unit washer/dryer, outdoor shower, and elevator access add everyday convenience. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, gas fire pits, and exceptional hospitality. A rare opportunity to own a luxury residence at one of Martha's Vineyard's most celebrated destinations. Harbor View Hotel retains a Right of First Refusal as outlined in the Master

This stunning custom-built waterfront estate offers sweeping views of Edgartown Harbor and exceptional craftsmanship throughout. Set on a private Chappaquiddick compound, the property features a beautifully designed main house, a separate one-bedroom guest house, a pool and spa, and expansive outdoor living spaces perfect for entertaining. Inside, warm wood finishes complement the home's comfortable scale, while the gourmet kitchen, spacious living room with a stone fireplace, and walls of windows showcase the spectacular harbor views. The second floor includes two queen suites, a bunkroom, and breathtaking water views from nearly every room. The finished lower level features a home theater and recreation room. A private path leads to the property's beach and deep-water dock, while a barn across the meadow offers a fitness center, guest suite, and basketball court. Cruise to Main Street Edgartown by skiff or take the nearby Chappy Ferry. This exceptional waterfront retreat offers the p

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 96 at 131 N. Water Street is a beautifully appointed 1061+/- sq. ft second and third-floor condominium featuring 3 beds and 3 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cooktop, microwave, and refrigerator/freezer. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Unit 96 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 94 at 131 N. Water Street is a beautifully appointed 730+/- sq. ft second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a microwave, and refrigerator/freezer. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Unit 94 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience

You truly can have it all-just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village, yet set along one of the most spectacular stretches of beach, with a 190' private dock with mooring and sweeping views across Edgartown Outer Harbor to the iconic Edgartown Lighthouse. A gentle slope leads to the sandy shore, where days unfold along the pristine waters of the harbor. Inside, casual elegance defines the home, with a seamless blend of gracious formal spaces and inviting areas for relaxed gatherings. An enclosed porch opens onto a spacious deck overlooking the harbor, creating the perfect setting to take in picture-worthy sunsets, the beloved Fourth of July fireworks display, and the ever-changing scenery. The grounds are equally captivating, made even more exceptional by the inclusion of 75 Landing Place Road and a beloved clay tennis court framed by sweeping water views. Cherished by the same family for generations, this extraordinary waterfront c

You truly can have it all-just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village, yet set along one of the most spectacular stretches of beach, with a 190' private dock with mooring and sweeping views across Edgartown Outer Harbor to the iconic Edgartown Lighthouse. A gentle slope leads to the sandy shore, where days unfold along the pristine waters of the harbor. Inside, casual elegance defines the home, with a seamless blend of gracious formal spaces and inviting areas for relaxed gatherings. An enclosed porch opens onto a spacious deck overlooking the harbor, creating the perfect setting to take in picture-worthy sunsets, the beloved Fourth of July fireworks display, and the ever-changing scenery. The grounds are equally captivating, made even more exceptional by the inclusion of 75 Landing Place Road and a beloved clay tennis court framed by sweeping water views. Cherished by the same family for generations, this extraordinary waterfront c

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 62 at 131 N. Water Street is a beautifully appointed 865+/- sq. ft second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cook-top stove, microwave, and refrigerator/freezer. An outdoor shower adds to everyday convenience. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Harbor View Hotel retains a Right of First Refusal as outlined in the Master Deed. Washer/Dryer and dedicated stora

Set amongst beautifully landscaped grounds and vibrant gardens, this inviting Chappaquiddick retreat offers a wonderful sense of privacy and tranquility. Stunning hydrangeas frame the property, also complemented by mature trees, colorful blooms, and established gardens, creating a beautiful setting throughout the seasons. Multiple outdoor spaces invite relaxing and entertaining, with a heated saltwater pool, completed in 2025, serving as the centerpiece. Inside, warm and inviting living spaces are filled with natural light, while shiplap details and a relaxed coastal aesthetic give the home a classic island feel. Vaulted ceilings and thoughtful attention to detail enhance the home's comfortable, refined character, while a thoughtfully designed single-level layout offers the ease and convenience of true first-floor living, with a private primary suite and separate guest wing providing an ideal sense of space and privacy. The detached studio with workshop is a hobbyist's dream, overlooki

An exceptional offering in the heart of Edgartown Village, 14 Thayer Street presents the rare combination of estate-scale grounds, privacy, and an in-town location. Set across an extraordinary 0.62-acre double lot, the property unfolds as a private retreat just moments from the harbor, shops, galleries, and restaurants of downtown Edgartown. Expansive lawns, mature landscaping, and a substantial swimming pool create a setting more often associated with properties well beyond the Village center, offering remarkable space for outdoor living, entertaining, and generations of summer gatherings. At the heart of the property is a distinguished five-bedroom, five-bath residence encompassing more than 3,100 square feet. Rich in authentic Vineyard character, the home is attributed to Frederick Baylies Jr builder of Edgartown's iconic Old Whaling Church, lending architectural significance to an already exceptional property. Yet it is the combination of land, location, and lifestyle that truly di

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 96 at 131 N. Water Street is a beautifully appointed 1061+/- sq. ft second and third-floor condominium featuring 3 beds and 3 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cooktop, microwave, and refrigerator/freezer. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Unit 96 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience

Edgartown Village Compound with Harbor Views: Positioned in the heart of Edgartown's historic district, 114 North Water Street is a newly complete, move-in-ready property offering views of Edgartown Harbor. The offering includes eight bedrooms and seven-and-a-half baths across three thoughtfully designed structures: a six-bedroom, five-and-a-half bath main residence, a one-bedroom guest house with full kitchen, and a two-car carriage house with additional living quarters. The property features a private backyard oasis with a 16' x 32' saltwater pool, spa, and pool cabana-an exceptional outdoor setting in Edgartown Village. With furnishings and window treatments included, the home is ready for immediate enjoyment. 114 North Water Street represents a turnkey Edgartown Village estate offering the scale, amenities, and setting that are seldom available in this iconic location

This stunning custom-built waterfront estate offers sweeping views of Edgartown Harbor and exceptional craftsmanship throughout. Set on a private Chappaquiddick compound, the property features a beautifully designed main house, a separate one-bedroom guest house, a pool and spa, and expansive outdoor living spaces perfect for entertaining. Inside, warm wood finishes complement the home's comfortable scale, while the gourmet kitchen, spacious living room with a stone fireplace, and walls of windows showcase the spectacular harbor views. The second floor includes two queen suites, a bunkroom, and breathtaking water views from nearly every room. The finished lower level features a home theater and recreation room. A private path leads to the property's beach and deep-water dock, while a barn across the meadow offers a fitness center, guest suite, and basketball court. Cruise to Main Street Edgartown by skiff or take the nearby Chappy Ferry. This exceptional waterfront retreat offers the p

This classic Edgartown Colonial is ideally situated in the heart of the village, just a short stroll from Fuller Street Beach, as well as Edgartown's acclaimed restaurants, boutiques, and harbor. Designed for comfortable coastal living and effortless entertaining, the open-concept floor plan flows seamlessly throughout the home. Offering 10 well-appointed rooms, the residence features six bedrooms, four full bathrooms, and two powder rooms. The gourmet kitchen opens to the spacious living and dining areas, creating an inviting gathering space that extends through French doors to a generous bluestone patio. The beautifully landscaped yard is highlighted by a private, thoughtfully sited swimming pool, providing a peaceful outdoor retreat perfect for relaxing or entertaining

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 94 at 131 N. Water Street is a beautifully appointed 730+/- sq. ft second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a microwave, and refrigerator/freezer. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Unit 94 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience

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

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 62 at 131 N. Water Street is a beautifully appointed 865+/- sq. ft second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cook-top stove, microwave, and refrigerator/freezer. An outdoor shower adds to everyday convenience. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Harbor View Hotel retains a Right of First Refusal as outlined in the Master Deed. Washer/Dryer and dedicated stora

An exceptional offering in the heart of Edgartown Village, 14 Thayer Street presents the rare combination of estate-scale grounds, privacy, and an in-town location. Set across an extraordinary 0.62-acre double lot, the property unfolds as a private retreat just moments from the harbor, shops, galleries, and restaurants of downtown Edgartown. Expansive lawns, mature landscaping, and a substantial swimming pool create a setting more often associated with properties well beyond the Village center, offering remarkable space for outdoor living, entertaining, and generations of summer gatherings. At the heart of the property is a distinguished five-bedroom, five-bath residence encompassing more than 3,100 square feet. Rich in authentic Vineyard character, the home is attributed to Frederick Baylies Jr. Builder of Edgartown

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest on Martha

An expansive compound in the heart of Edgartown village does not come to the market very often. A stunning renovation by Stern McCafferty Architecture + Interiors has yielded a home that seamlessly blends the old and new, the historic with the contemporary. Light, bright, and with the highest levels of finished detail, the home is filled with details to remind you that you are in one of the most richly historic communities in all of New England. Just look out the front windows and watch the yachts pass between the beautiful waterfront homes and it calls to mind that only a few generations ago it was whaling vessels that dominated the water views and the homes themselves belonged to successful ship

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank