Chappaquiddick
Chappaquiddick, commonly referred to as Chappy, is a small island (about 5 miles long x 3 miles wide) off the eastern end of Edgartown. The mainland of Edgartown and Chappy are sometimes connected, along their southern coast, by a narrow barrier beach only accessible by 4-wheel drive vehicles. The southeastern point of this beach is called Wasque Point – a popular fishing spot especially during the annual Martha's Vineyard Striped Bass and Bluefish Derby held each fall. Chappy boasts numerous wildlife preserves and pristine beaches and offers a more remote, slower pace of life, and yet is just minutes from Edgartown Village. With no commercial center or stores, when one needs or wants to go into town, a bargelike ferry called the On Time shuttles up to three cars, passengers and cyclists to and from the Village. If you feel Chappy checks all the boxes for your summer vacation location, we have a large inventory of homes that includes quaint camps to large waterfront estates.
54 properties available
Easy to access, "Retreat House", a two-bedroom guest house, is nestled between Chappaquiddick's paved road and the waterfront. Enjoy the sweeping ocean view from the dining table as you sip your morning coffee or from either bedroom. The first-floor primary bedroom features a large en suite bathroom with shower. Up the stairs, the second bedroom wi
Edgartown Chappaquiddick 435
Easy to access, "Retreat House", a two-bedroom guest house, is nestled between Chappaquiddick's paved road and the waterfront. Enjoy the sweeping ocea... Read More
Easy to access, "Retreat House", a two-bedroom guest house, is nestled between Chappaquiddick's paved road and the waterfront. Enjoy the sweeping ocea... Read More
Step back, relax and unwind in this single-story contemporary with an open floor plan, lots of windows and vaulted ceilings. Enjoy nearby Katama Bay, perfect for swimming and shell fishing, as well as the sand and surf of Washque beach down the road. If you enjoy tennis, bring your rackets as neighborhood courts are within walking distance. This is
Edgartown Chappaquiddick 485
Step back, relax and unwind in this single-story contemporary with an open floor plan, lots of windows and vaulted ceilings. Enjoy nearby Katama Bay, ... Read More
Step back, relax and unwind in this single-story contemporary with an open floor plan, lots of windows and vaulted ceilings. Enjoy nearby Katama Bay, ... Read More
This spacious 5 Bedroom home with a brand-new 20x60 saltwater pool and 8x12 hot tub is the ultimate Chappy getaway. Walk into the main level and you will find 4 of the 5 bedrooms, 2 full bathrooms and comfortable living space. Upstairs is the main living area, open concept kitchen, dining space, and primary en suite bedroom which all offer stunning
Edgartown Chappaquiddick 421
This spacious 5 Bedroom home with a brand-new 20x60 saltwater pool and 8x12 hot tub is the ultimate Chappy getaway. Walk into the main level and you w... Read More
This spacious 5 Bedroom home with a brand-new 20x60 saltwater pool and 8x12 hot tub is the ultimate Chappy getaway. Walk into the main level and you w... Read More
Immerse yourself in laid-back Chappaquiddick living at this quaint two bedroom cottage with association water access at the end of the road and close proximity to Wasque beach. From the moment you arrive, you will feel like you have gone back in time to a quiet retreat. This fully air conditioned, one-level home offers comfortable living space to r
Edgartown Chappaquiddick 386
Immerse yourself in laid-back Chappaquiddick living at this quaint two bedroom cottage with association water access at the end of the road and close ... Read More
Immerse yourself in laid-back Chappaquiddick living at this quaint two bedroom cottage with association water access at the end of the road and close ... Read More
Spectacular 180 degree views, set up high overlooking Cape Pogue. This three bedroom pet friendly single level home with wonderful views. Features an open kitchen, living and dining area with sliders that open out to an outdoor deck. An added bonus of two of the three bedrooms offering gorgeous water views. Additional sleeping with a queen bed lo
Edgartown Chappaquiddick 408
Spectacular 180 degree views, set up high overlooking Cape Pogue. This three bedroom pet friendly single level home with wonderful views. Features an ... Read More
Spectacular 180 degree views, set up high overlooking Cape Pogue. This three bedroom pet friendly single level home with wonderful views. Features an ... Read More
Set along the shores of Chappaquiddick, this remarkable estate seamlessly blends privacy and elegance with direct access to the water. At the heart of the property lies an impressive 140-foot deep-water dock, complemented by a stunning five-bedroom main house and a charming three-bedroom guesthouse, making it an ideal venue for both leisure and ent
Edgartown Chappaquiddick 337
Set along the shores of Chappaquiddick, this remarkable estate seamlessly blends privacy and elegance with direct access to the water. At the heart of... Read More
Set along the shores of Chappaquiddick, this remarkable estate seamlessly blends privacy and elegance with direct access to the water. At the heart of... Read More
NOTE: All new furnishings for 2026, not pictured. This house sings the harmony of a well-traveled Vineyarder. Embodying all the essentials, just enough space, perfectly composed, effortlessly chic. A thoughtfully designed single-story Chappaquiddick cottage with two bedrooms and two full baths, including one ensuite and an open kitchen and living a
Edgartown Chappaquiddick 306
NOTE: All new furnishings for 2026, not pictured. This house sings the harmony of a well-traveled Vineyarder. Embodying all the essentials, just enoug... Read More
NOTE: All new furnishings for 2026, not pictured. This house sings the harmony of a well-traveled Vineyarder. Embodying all the essentials, just enoug... Read More
Sitting atop Wasque Hill, the highest house on Chappaquiddick, rests among three forested acres. This dramatic home offers 360-degree views of Chappaquiddick with all the drama of spectacular evening sunsets and sparkling distant views of Katama Bay and Nantucket Sound beyond from the deck. The main house offers lovely, reverse-style living with th
Edgartown Chappaquiddick 488
Sitting atop Wasque Hill, the highest house on Chappaquiddick, rests among three forested acres. This dramatic home offers 360-degree views of Chappaq... Read More
Sitting atop Wasque Hill, the highest house on Chappaquiddick, rests among three forested acres. This dramatic home offers 360-degree views of Chappaq... Read More
Discover the perfect island getaway with this charming five-bedroom home. Unique craftsmanship throughout this home is ideal for families and groups seeking relaxation and adventure. Tucked away near Chappaquiddick's pristine beaches, this inviting retreat offers the perfect blend of comfort and coastal charm. Inside, you'll find a thoughtfully des
Edgartown Chappaquiddick 419
Discover the perfect island getaway with this charming five-bedroom home. Unique craftsmanship throughout this home is ideal for families and groups s... Read More
Discover the perfect island getaway with this charming five-bedroom home. Unique craftsmanship throughout this home is ideal for families and groups s... Read More
Set back among mature trees on Chappaquiddick, this classic Cape-style home offers comfortable space for a traditional island week. With 4 bedrooms and 2 bathrooms accommodating up to 10 guests, the layout works well for extended family stays or shared summer rentals in a quiet location near the ferry.
Enter into the welcoming living room, which co
Edgartown Chappaquiddick 342
Set back among mature trees on Chappaquiddick, this classic Cape-style home offers comfortable space for a traditional island week. With 4 bedrooms an... Read More
Set back among mature trees on Chappaquiddick, this classic Cape-style home offers comfortable space for a traditional island week. With 4 bedrooms an... Read More
Ocean all around! This is the perfect Chappy retreat for your family vacation. Stunning views from almost every room featuring all new furnishings in 2023 and a brand new luxury kitchen in 2025. Enjoy the easy summer days on Chappy relaxing at the beach or simply reading a book on the deck. Feels like rolling back time to simpler days to enjoy what
Edgartown Chappaquiddick 316
Ocean all around! This is the perfect Chappy retreat for your family vacation. Stunning views from almost every room featuring all new furnishings in ... Read More
Ocean all around! This is the perfect Chappy retreat for your family vacation. Stunning views from almost every room featuring all new furnishings in ... Read More
Relax in this Chappy three bedroom reverse-style cottage located at the entrance to Wasque and take advantage of the pristine beaches and the serene setting. Light and airy open concept living area on the second floor with bedrooms on the first floor make up this comfortable vacation retreat with water views of Katama Bay and Norton's Point. (Win
Edgartown Chappaquiddick 374
Relax in this Chappy three bedroom reverse-style cottage located at the entrance to Wasque and take advantage of the pristine beaches and the serene s... Read More
Relax in this Chappy three bedroom reverse-style cottage located at the entrance to Wasque and take advantage of the pristine beaches and the serene s... Read More
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