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 house sings the harmony of a well-traveled Vineyarder. Embodying all the essentials with just enough space, perfectly composed and effortlessly chic. Property sleeps 8 with three bedrooms, an additional sleeping area on the first floor, and two full baths divided between the first and second floor. Open concept kitchen, living and dining area
Edgartown Chappaquiddick 301
This house sings the harmony of a well-traveled Vineyarder. Embodying all the essentials with just enough space, perfectly composed and effortlessly c... Read More
This house sings the harmony of a well-traveled Vineyarder. Embodying all the essentials with just enough space, perfectly composed and effortlessly c... 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
Less than a mile from the Quammox Preserve beach, this charming two-bedroom home on Chappaquiddick, built in 2018, offers a bright and inviting open-concept layout. The modern kitchen and dining area flow seamlessly into the living room and onto a spacious outdoor porch—perfect for relaxed island living. The main level features a primary en suite b
Edgartown Chappaquiddick 491
Less than a mile from the Quammox Preserve beach, this charming two-bedroom home on Chappaquiddick, built in 2018, offers a bright and inviting open-c... Read More
Less than a mile from the Quammox Preserve beach, this charming two-bedroom home on Chappaquiddick, built in 2018, offers a bright and inviting open-c... 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
Chappy two bedroom cottage named the Mizzen. All of your basic needs are covered with charm and great location. Spectacular views out to the Vineyard Sound and Edgartown Lighthouse. Easy access to the Chappy ferry and just minutes to the Chappy community center offering wonderful family activities including tennis, sailing, kayaking, hiking trail
Edgartown Chappaquiddick 321
Chappy two bedroom cottage named the Mizzen. All of your basic needs are covered with charm and great location. Spectacular views out to the Vineyard... Read More
Chappy two bedroom cottage named the Mizzen. All of your basic needs are covered with charm and great location. Spectacular views out to the Vineyard... Read More
Chappaquiddick waterfront with a dock! Two stunning cottages rent together on the inner harbor, The Boathouse and A-Frame. Your dream come true with these beautifully restored cottages surrounded by water. The Boathouse has been fully updated to modern standards and takes full advantage of space in each room. Surprisingly roomy and sleeps seven,
Edgartown Chappaquiddick 311
Chappaquiddick waterfront with a dock! Two stunning cottages rent together on the inner harbor, The Boathouse and A-Frame. Your dream come true with ... Read More
Chappaquiddick waterfront with a dock! Two stunning cottages rent together on the inner harbor, The Boathouse and A-Frame. Your dream come true with ... 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
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
Chappaquiddick on Martha's Vineyard, amazing single level cottage lovingly renovated to make your stay more comfortable and enjoyable. Updated appliances in the kitchen, ac mini splits and heat units in all three bedrooms and living room. A comfortable living room and screened porch to relax and unwind. Great location, just one mile from My Toi, Di
Edgartown Chappaquiddick 323
Chappaquiddick on Martha's Vineyard, amazing single level cottage lovingly renovated to make your stay more comfortable and enjoyable. Updated applian... Read More
Chappaquiddick on Martha's Vineyard, amazing single level cottage lovingly renovated to make your stay more comfortable and enjoyable. Updated applian... Read More
Ocean all around! This is the perfect Chappy retreat for your family vacation. Stunning views from almost every room featuring all new furnishings in 2023 and a brand new luxury kitchen in 2025. Enjoy the easy summer days on Chappy relaxing at the beach or simply reading a book on the deck. Feels like rolling back time to simpler days to enjoy what
Edgartown Chappaquiddick 316
Ocean all around! This is the perfect Chappy retreat for your family vacation. Stunning views from almost every room featuring all new furnishings in ... Read More
Ocean all around! This is the perfect Chappy retreat for your family vacation. Stunning views from almost every room featuring all new furnishings in ... 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 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
Vintage Chappaquiddick home on Martha's Vineyard at the Snows Point. This five bedroom main house overlooks Katama Bay with expansive views of boats sailing by. There is a sandy beach in front of the house just steps away with an association dock which is excellent for fishing, acres of lawn and an enclosed vegetable and flower garden. Inside you w
Edgartown Chappaquiddick 304
Vintage Chappaquiddick home on Martha's Vineyard at the Snows Point. This five bedroom main house overlooks Katama Bay with expansive views of boats s... Read More
Vintage Chappaquiddick home on Martha's Vineyard at the Snows Point. This five bedroom main house overlooks Katama Bay with expansive views of boats s... Read More
Tell us what you're looking for and someone will contact you with available options.
