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.
55 properties available
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
Vintage Chappaquiddick home on Martha's Vineyard at the Snows Point. This five bedroom main house overlooks Katama Bay with expansive views of boats sailing by. There is a sandy beach in front of the house just steps away with an association dock which is excellent for fishing, acres of lawn and an enclosed vegetable and flower garden. Inside you w
Edgartown Chappaquiddick 304
Vintage Chappaquiddick home on Martha's Vineyard at the Snows Point. This five bedroom main house overlooks Katama Bay with expansive views of boats s... Read More
Vintage Chappaquiddick home on Martha's Vineyard at the Snows Point. This five bedroom main house overlooks Katama Bay with expansive views of boats 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 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
Chappy pet-friendly, three-bedroom colonial in a quiet area close to East Beach. From the open living space, sun on the deck or nap on the screened porch. Laundry conveniently located just inside the door and close to outside shower. Den with TV and powder room round out the first floor. The king primary and other two bedrooms that share a hall
Edgartown Chappaquiddick 415
Chappy pet-friendly, three-bedroom colonial in a quiet area close to East Beach. From the open living space, sun on the deck or nap on the screened po... Read More
Chappy pet-friendly, three-bedroom colonial in a quiet area close to East Beach. From the open living space, sun on the deck or nap on the screened po... Read More
Chappaquiddick waterfront with a dock! Two stunning cottages rent together on the inner harbor, The Boathouse and A-Frame. Your dream come true with these beautifully restored cottages surrounded by water. The Boathouse has been fully updated to modern standards and takes full advantage of space in each room. Surprisingly roomy and sleeps seven,
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Chappaquiddick waterfront with a dock! Two stunning cottages rent together on the inner harbor, The Boathouse and A-Frame. Your dream come true with ... Read More
Chappaquiddick waterfront with a dock! Two stunning cottages rent together on the inner harbor, The Boathouse and A-Frame. Your dream come true with ... Read More
Converted barn with access to Katama Bay along with lovely water views. The spacious open living space spills out to an outdoor patio. The second-floor bedrooms are located on one end of the barn and an open loft area for additional sleeping at the other end. Spend the day on the private beach just a 5-minute walk away or enjoy a hike around the p
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Converted barn with access to Katama Bay along with lovely water views. The spacious open living space spills out to an outdoor patio. The second-flo... Read More
Converted barn with access to Katama Bay along with lovely water views. The spacious open living space spills out to an outdoor patio. The second-flo... Read More
A pristine Chappy property on the top of Manaca Hill, with water views of Katama Bay and Edgartown harbor. This custom gambrel home offers a large, open concept kitchen with large center island and living room, complete with a game table. Double glass doors ensure a nearly uninterrupted view, relax on the patio or the four-season porch. Inside, the
Edgartown Chappaquiddick 495
A pristine Chappy property on the top of Manaca Hill, with water views of Katama Bay and Edgartown harbor. This custom gambrel home offers a large, op... Read More
A pristine Chappy property on the top of Manaca Hill, with water views of Katama Bay and Edgartown harbor. This custom gambrel home offers a large, op... 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
Chappaquiddick reverse-style three-bedroom home a short distance to Katama Bay (via association stairs). The kitchen and dining flow nicely to the full deck to enjoy outdoor dining and grilling. Just behind the living area is the primary bedroom with queen bed and private bath. There are two first-floor bedrooms, shared hall bath with tub and sh
Edgartown Chappaquiddick 411
Chappaquiddick reverse-style three-bedroom home a short distance to Katama Bay (via association stairs). The kitchen and dining flow nicely to the fu... Read More
Chappaquiddick reverse-style three-bedroom home a short distance to Katama Bay (via association stairs). The kitchen and dining flow nicely to the fu... 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
This three bedroom reverse-style home, close to Wasque beach, offers distant views from the second floor. A full length deck, off the galley kitchen and spacious living room, allows for dining inside or out. The second floor bedroom has access to the deck as well. The remaining two bedrooms on the first floor share a hall bath. Large yard and a
Edgartown Chappaquiddick 493
This three bedroom reverse-style home, close to Wasque beach, offers distant views from the second floor. A full length deck, off the galley kitchen ... Read More
This three bedroom reverse-style home, close to Wasque beach, offers distant views from the second floor. A full length deck, off the galley kitchen ... Read More
An idealistic Chappaquiddick retreat, with all the comforts of home. Private location, great deck area for outdoor entertaining. Room abounds - with privacy and tranquility galore. Additional sleeping space in the newly finished lower level with full bath, fireplace and laundry. A short drive to Wasque beach via Trustees access. Shared tennis cou
Edgartown Chappaquiddick 318
An idealistic Chappaquiddick retreat, with all the comforts of home. Private location, great deck area for outdoor entertaining. Room abounds - with ... Read More
An idealistic Chappaquiddick retreat, with all the comforts of home. Private location, great deck area for outdoor entertaining. Room abounds - with ... Read More
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