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 charming three-bedroom cottage features an open kitchen, dining, and living area. On the first floor, two bedrooms have access to a shared hall bathroom. The second floor boasts a spacious king suite complete with a private bath. Both the king bedroom and the living area are equipped with AC mini-split units for added comfort. The cottage is l
Edgartown Chappaquiddick 407
This charming three-bedroom cottage features an open kitchen, dining, and living area. On the first floor, two bedrooms have access to a shared hall b... Read More
This charming three-bedroom cottage features an open kitchen, dining, and living area. On the first floor, two bedrooms have access to a shared hall b... 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
A cottage by the bay... pulled from the pages of a seaside novel. This charming two-bedroom home has been renovated and fully updated with an open concept kitchen and dining area, flowing seamlessly into the living room and outdoor porch. Reminiscent of the stolen summers from years ago, evenings filled with ocean breezes and quiet afternoons, free
Edgartown Chappaquiddick 327
A cottage by the bay... pulled from the pages of a seaside novel. This charming two-bedroom home has been renovated and fully updated with an open con... Read More
A cottage by the bay... pulled from the pages of a seaside novel. This charming two-bedroom home has been renovated and fully updated with an open con... 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 with a newly renovated kitchen (2026) on the second floor. Bedrooms on the first floor make up this comfortable vacation retreat with water views of Ka
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
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
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 area. Enjoy the dynamic, panoramic views of the ou
Edgartown Chappaquiddick 306
This house sings the harmony of a well-traveled Vineyarder. Embodying all the essentials, just enough space, perfectly composed, effortlessly chic. A ... Read More
This house sings the harmony of a well-traveled Vineyarder. Embodying all the essentials, just enough space, perfectly composed, effortlessly chic. A ... Read More
Stunning Chappaquiddick four bedroom home with water views. Spacious open living and kitchen area. Dining room features an open cathedral ceiling to the second floor with interior balcony. Beautifully designed to capture the feel of both Chappaquiddick and modern living. Water views abound from primary bedroom and both upper and lower screened p
Edgartown Chappaquiddick 364
Stunning Chappaquiddick four bedroom home with water views. Spacious open living and kitchen area. Dining room features an open cathedral ceiling to... Read More
Stunning Chappaquiddick four bedroom home with water views. Spacious open living and kitchen area. Dining room features an open cathedral ceiling to... 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
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
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
This five bedroom home is truly a quintessential Chappy retreat. Set in the woods, this property offers privacy and a beautiful distant view of Edgartown Harbor down a long and sloping lawn. With its large outdoor deck and inviting wide open interior, this home provides a wonderful space to explore, relax, and entertain both inside and out. An inte
Edgartown Chappaquiddick 387
This five bedroom home is truly a quintessential Chappy retreat. Set in the woods, this property offers privacy and a beautiful distant view of Edgart... Read More
This five bedroom home is truly a quintessential Chappy retreat. Set in the woods, this property offers privacy and a beautiful distant view of Edgart... Read More
Chappaquiddick four-bedroom reverse-style home, accentuating the breathtaking views of Katama Bay and the ocean. An outdoor deck on the upper living area offers plenty of comfy loungers, dining table and chairs to either catch a nap or just enjoy the solitude. The living space, including, sunroom is bright and airy. On the main level, three queen
Edgartown Chappaquiddick 331
Chappaquiddick four-bedroom reverse-style home, accentuating the breathtaking views of Katama Bay and the ocean. An outdoor deck on the upper living a... Read More
Chappaquiddick four-bedroom reverse-style home, accentuating the breathtaking views of Katama Bay and the ocean. An outdoor deck on the upper living a... Read More
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