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
A captivating marriage of structure and surrounding yields an absolute masterpiece of eco-conscious modern architecture with some of the most beautiful views on the Vineyard, Nantucket Sound to the east and Edgartown harbor to the west. This seven bedroom home was designed with the utmost consideration for both the land and the locale. Built with
Edgartown Chappaquiddick 310
A captivating marriage of structure and surrounding yields an absolute masterpiece of eco-conscious modern architecture with some of the most beautifu... Read More
A captivating marriage of structure and surrounding yields an absolute masterpiece of eco-conscious modern architecture with some of the most beautifu... Read More
An architectural dream come true, built as a labor of love. Beautifully sited on a bluff overlooking Edgartown harbor. Naturally ventilated by ocean breezes enhanced by ceiling fans throughout. Many rooms with views and some that open out to a deck overlooking the harbor. This authentic Chappy beach house is truly a vacation to experience, calm oce
Edgartown Chappaquiddick 317
An architectural dream come true, built as a labor of love. Beautifully sited on a bluff overlooking Edgartown harbor. Naturally ventilated by ocean b... Read More
An architectural dream come true, built as a labor of love. Beautifully sited on a bluff overlooking Edgartown harbor. Naturally ventilated by ocean b... Read More
Custom Chappaquiddick contemporary, with separate guest house, nestled on three wooded acres. Located far enough from the main road to be quiet and relaxing but convenient to the Chappy Ferry and Chappaquiddick Community Center. The kitchen, dining, and living rooms are separated from the two primary king suites, by an extra sitting area. Each roo
Edgartown Chappaquiddick 396
Custom Chappaquiddick contemporary, with separate guest house, nestled on three wooded acres. Located far enough from the main road to be quiet and r... Read More
Custom Chappaquiddick contemporary, with separate guest house, nestled on three wooded acres. Located far enough from the main road to be quiet and r... 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
 Discover the ultimate 5-bedroom retreat, where luxury and relaxation converge to redefine your vacation experience. This top-of-the-line, two-story home features central air, an inviting swimming pool, and ocean views. Enjoy the spacious elegance and bright living spaces in the main house, featuring an en suite bedroom conveniently located on the
Edgartown Chappaquiddick 300
 Discover the ultimate 5-bedroom retreat, where luxury and relaxation converge to redefine your vacation experience. This top-of-the-line, two-story h... Read More
 Discover the ultimate 5-bedroom retreat, where luxury and relaxation converge to redefine your vacation experience. This top-of-the-line, two-story h... Read More
This lovely contemporary Cape offers quiet tranquility yet great proximity to beach, ferry and the Chappaquiddick Community Center. Spend your days relaxing at Wasque beach, biking Chappy, exploring the wonderful open trails or taking a quick trip into town and return to enjoy the large private deck. Inside you will find two bedrooms on the first f
Edgartown Chappaquiddick 359
This lovely contemporary Cape offers quiet tranquility yet great proximity to beach, ferry and the Chappaquiddick Community Center. Spend your days re... Read More
This lovely contemporary Cape offers quiet tranquility yet great proximity to beach, ferry and the Chappaquiddick Community Center. Spend your days re... Read More
Piece of heaven on Chappy. You will enjoy this property from the moment you enter with a grand view of Katama Bay right from the entrance. Beautifully furnished reverse level home with peaked ceilings and open space maximizes this stunning location. Views from kitchen, living and dining out to a substantial deck is made for entertaining and loun
Edgartown Chappaquiddick 397
Piece of heaven on Chappy. You will enjoy this property from the moment you enter with a grand view of Katama Bay right from the entrance. Beautiful... Read More
Piece of heaven on Chappy. You will enjoy this property from the moment you enter with a grand view of Katama Bay right from the entrance. Beautiful... 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
A classic reverse-style contemporary with peeks of Katama Bay from the widows walk. The living area is open and airy with high ceilings and there is plenty of outdoor space - screened porch, deck and patio - to feel the essence of the beach. Three bedrooms on first floor share one full and one half baths. Just down the road from the calm waters of
Edgartown Chappaquiddick 373
A classic reverse-style contemporary with peeks of Katama Bay from the widows walk. The living area is open and airy with high ceilings and there is p... Read More
A classic reverse-style contemporary with peeks of Katama Bay from the widows walk. The living area is open and airy with high ceilings and there is p... 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
Edgartown Chappaquiddick 434
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
This charming and well-maintained beach house, "Seas the Day," is situated in a private wooded area of Chappaquiddick, just around 1.5 miles from East Beach. The kitchen is well-equipped with granite countertops, and the open floor plan encourages plenty of relaxation on the comfortable sofas or in the screened porch. It's a wonderful way to enjoy
Edgartown Chappaquiddick 399
This charming and well-maintained beach house, "Seas the Day," is situated in a private wooded area of Chappaquiddick, just around 1.5 miles from East... Read More
This charming and well-maintained beach house, "Seas the Day," is situated in a private wooded area of Chappaquiddick, just around 1.5 miles from East... 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
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