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
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 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
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
Arrive on Chappy via the iconic "On Time" ferry and as you travel along Chappaquiddick Road, you're greeted by the picturesque landscape offering a sense of solitude with the open ocean on your left and charming homes tucked away on the side streets. This home is about 2.5 miles from the ferry and about half way to Wasque Reservation. Open fields s
Edgartown Chappaquiddick 330
Arrive on Chappy via the iconic "On Time" ferry and as you travel along Chappaquiddick Road, you're greeted by the picturesque landscape offering a se... Read More
Arrive on Chappy via the iconic "On Time" ferry and as you travel along Chappaquiddick Road, you're greeted by the picturesque landscape offering a se... 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
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
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
This spacious four-bedroom home is the ultimate Chappaquiddick vacation retreat. Designed in a reverse-style layout, it features an open-concept second-floor living, dining, and kitchen area, complemented by two three-season porches—ideal for entertaining guests. The first floor is home to the primary en suite bedroom, complete with its own private
Edgartown Chappaquiddick 357
This spacious four-bedroom home is the ultimate Chappaquiddick vacation retreat. Designed in a reverse-style layout, it features an open-concept secon... Read More
This spacious four-bedroom home is the ultimate Chappaquiddick vacation retreat. Designed in a reverse-style layout, it features an open-concept secon... Read More
This Charming Chappaquiddick 2 bedroom home has been lovingly updated and boasts an additional bedroom and full en suite bathroom in the garage apartment with private access. The main house has Central AC throughout and a Mini Split unit keeps the guest apartment cool. Settle in and enjoy the fully equipped newly renovated kitchen (2026), main floo
Edgartown Chappaquiddick 343
This Charming Chappaquiddick 2 bedroom home has been lovingly updated and boasts an additional bedroom and full en suite bathroom in the garage apartm... Read More
This Charming Chappaquiddick 2 bedroom home has been lovingly updated and boasts an additional bedroom and full en suite bathroom in the garage apartm... 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
Chappy at it finest! Enjoy this well-appointed four bedroom home near Wasque and Packard Preserve trail to the inner harbor. A perfect getaway for your family and friends ~ soak in the lovely summer breezes on the first floor screened porch overlooking an expansive lawn or on the second floor deck with peeks of the water over the treetops. This
Edgartown Chappaquiddick 358
Chappy at it finest! Enjoy this well-appointed four bedroom home near Wasque and Packard Preserve trail to the inner harbor. A perfect getaway for y... Read More
Chappy at it finest! Enjoy this well-appointed four bedroom home near Wasque and Packard Preserve trail to the inner harbor. A perfect getaway for y... 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
Tell us what you're looking for and someone will contact you with available options.
