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
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
This charming and meticulously cared-for two-bedroom cape is situated in a quiet wooded area of Chappaquiddick. Its convenient location is just about 1.5 miles from Pogue Beach, perfect for families looking to swim, fish, or enjoy a four-wheel drive adventure through the dunes. The cozy cottage features a well-equipped kitchen along with a spacious
Edgartown Chappaquiddick 325
This charming and meticulously cared-for two-bedroom cape is situated in a quiet wooded area of Chappaquiddick. Its convenient location is just about ... Read More
This charming and meticulously cared-for two-bedroom cape is situated in a quiet wooded area of Chappaquiddick. Its convenient location is just about ... 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
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
Enjoy life's simple pleasures at this two bedroom Chappy cottage named the Rudder. Stunning views over the Vineyard Sound with a beautiful porch to lounge and admire the perfect setting. Perfectly located close to the Chappy ferry and community center and just a few miles to one of the most desirable South Shore beaches on Martha's Vineyard at Was
Edgartown Chappaquiddick 319
Enjoy life's simple pleasures at this two bedroom Chappy cottage named the Rudder. Stunning views over the Vineyard Sound with a beautiful porch to lo... Read More
Enjoy life's simple pleasures at this two bedroom Chappy cottage named the Rudder. Stunning views over the Vineyard Sound with a beautiful porch to lo... Read More
Charming Chappy boathouse rental with views of Edgartown outer harbor. Reminiscent of seasons past, with updated kitchen and baths, this adorable three-bedroom cottage provides all the comforts in a perfect location to enjoy your Martha's Vineyard vacation. Main bedroom located on the first floor and the two twin bedrooms on the second floor. The
Edgartown Chappaquiddick 449
Charming Chappy boathouse rental with views of Edgartown outer harbor. Reminiscent of seasons past, with updated kitchen and baths, this adorable thr... Read More
Charming Chappy boathouse rental with views of Edgartown outer harbor. Reminiscent of seasons past, with updated kitchen and baths, this adorable thr... 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
Chappy four-bedroom contemporary with distant water views and access to Katama Bay is a wonderful retreat for all to experience. An added bonus is the large screened porch with field stone fireplace located as an anchor, accentuating the glorious scenic view. First-floor queen primary en suite with access to the first floor deck. Leading up the we
Edgartown Chappaquiddick 395
Chappy four-bedroom contemporary with distant water views and access to Katama Bay is a wonderful retreat for all to experience. An added bonus is the... Read More
Chappy four-bedroom contemporary with distant water views and access to Katama Bay is a wonderful retreat for all to experience. An added bonus is the... Read More
Chappaquiddick waterfront rental with spectacular views. Wonderful, spacious old vineyard beach house with private beach. Two of the eight bedrooms are on the first floor, while the primary en suite with waterviews and other five bedrooms occupy the second floor. Two kitchens, two living rooms, den, and screened porch. Spend the day on the priva
Edgartown Chappaquiddick 432
Chappaquiddick waterfront rental with spectacular views. Wonderful, spacious old vineyard beach house with private beach. Two of the eight bedrooms a... Read More
Chappaquiddick waterfront rental with spectacular views. Wonderful, spacious old vineyard beach house with private beach. Two of the eight bedrooms a... Read More
Edgartown Chappaquiddick 313
Martha's Vineyard vacation three-bedroom cottage by the sea. Located on the south side of Chappaquiddick Island, it is adjacent to the Trustees Wasque... Read More
Martha's Vineyard vacation three-bedroom cottage by the sea. Located on the south side of Chappaquiddick Island, it is adjacent to the Trustees Wasque... Read More
Charming 5-bedroom farmhouse with great views of Katama Bay. Kitchen with breakfast table abuts the large, sun porch which doubles as a dining room. For quiet time relax in the living room at the front of the house. The main bedroom and one with two twins complete the first floor. The remaining three bedrooms on the second floor share a hall b
Edgartown Chappaquiddick 433
Charming 5-bedroom farmhouse with great views of Katama Bay. Kitchen with breakfast table abuts the large, sun porch which doubles as a dining room. ... Read More
Charming 5-bedroom farmhouse with great views of Katama Bay. Kitchen with breakfast table abuts the large, sun porch which doubles as a dining room. ... 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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