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
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
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
Step back, relax and unwind in this single-story contemporary with an open floor plan, lots of windows and vaulted ceilings. Enjoy nearby Katama Bay, perfect for swimming and shell fishing, as well as the sand and surf of Washque beach down the road. If you enjoy tennis, bring your rackets as neighborhood courts are within walking distance. This is
Edgartown Chappaquiddick 485
Step back, relax and unwind in this single-story contemporary with an open floor plan, lots of windows and vaulted ceilings. Enjoy nearby Katama Bay, ... Read More
Step back, relax and unwind in this single-story contemporary with an open floor plan, lots of windows and vaulted ceilings. Enjoy nearby Katama Bay, ... 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
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
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
Easy to access, "Retreat House", a two-bedroom guest house, is nestled between Chappaquiddick's paved road and the waterfront. Enjoy the sweeping ocean view from the dining table as you sip your morning coffee or from either bedroom. The first-floor primary bedroom features a large en suite bathroom with shower. Up the stairs, the second bedroom wi
Edgartown Chappaquiddick 435
Easy to access, "Retreat House", a two-bedroom guest house, is nestled between Chappaquiddick's paved road and the waterfront. Enjoy the sweeping ocea... Read More
Easy to access, "Retreat House", a two-bedroom guest house, is nestled between Chappaquiddick's paved road and the waterfront. Enjoy the sweeping ocea... 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
Take a three minute ferry ride from the village of Edgartown to arrive at this stunning Four Bedroom waterfront home located on Chappaquiddick Island. Plenty of space for entertaining with a large open dining and living area, opening out onto the deck. Recently updated, the house offers up-scale amenities and Central AC for those warm summer nights
Edgartown Chappaquiddick 418
Take a three minute ferry ride from the village of Edgartown to arrive at this stunning Four Bedroom waterfront home located on Chappaquiddick Island.... Read More
Take a three minute ferry ride from the village of Edgartown to arrive at this stunning Four Bedroom waterfront home located on Chappaquiddick Island.... Read More
Three-bedroom Chappy property with front porch and distant views of Katama Bay and South beach. Private setting with a large outdoor deck area for relaxing and entertaining. All three queen bedrooms on the second floor of the main house and detached guesthouse joined by an outdoor deck includes a family room, game room area and extra sleeping accom
Edgartown Chappaquiddick 303
Three-bedroom Chappy property with front porch and distant views of Katama Bay and South beach. Private setting with a large outdoor deck area for rel... Read More
Three-bedroom Chappy property with front porch and distant views of Katama Bay and South beach. Private setting with a large outdoor deck area for rel... 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
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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