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
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
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
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
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
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
Brand new to the rental market: a new rendition of a classic Chappy home with a private dock and beach access -- renovations include an interior refresh: crisp white walls and vaulted ceilings, new bathrooms, air conditioning, all new furnishings - understated luxury, surrounded by 180-degree water views over Edgartown Harbor and Cape Pogue from th
Edgartown Chappaquiddick 305
Brand new to the rental market: a new rendition of a classic Chappy home with a private dock and beach access -- renovations include an interior refre... Read More
Brand new to the rental market: a new rendition of a classic Chappy home with a private dock and beach access -- renovations include an interior refre... 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
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
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
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
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
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
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