OysterNest: Chappy Waterfront, Beach, Dock & Spa

Welcome to OysterNest, a classic shingled waterfront estate on more than three and a half private acres on Chappaquiddick, just minutes from Edgartown village by the Chappy ferry. With its own sandy beach, a 140-foot deepwater dock with two floating platforms, and wide-open views across Nantucket Sound, this is a true Vineyard compound for families and groups who want space, privacy and the shoreline right outside the door.

The five-bedroom main house is filled with natural light and timeless island character: fir floors, white shiplap and water views from nearly every room. The first floor flows from a generous living room with a fireplace to the dining room and a bright kitchen with a large island and pantry, along with a den, home office, mudroom and powder room. Upstairs, the primary suite includes its own reading room.

The lower level is a private spa and fitness space with an exercise area, massage room, steam room, sauna and full bath. A separate three-bedroom guest house with its own kitchen and living area gives visiting family and friends a place of their own.

Outside, a long covered porch on locust posts, a screened porch and a deck look out over rolling lawns to the water. Spend the day on the private beach, bring the boat right up to the dock (suited to boats with a 6 to 8 foot draft), or gather in the Adirondack chairs at sunset. The property sits across from the Royal and Ancient Chappaquiddick Links.

Central air conditioning, Wi-Fi, a ping pong table, washer and dryer, an outdoor shower and linens are all included.

Bedroom & Bathroom Details

Bedroom One - Main House, First Floor: Queen bed, shared bath.

Bedroom Two - Main House, First Floor: Two twin beds, shared bath.

Bedroom Three - Main House, Second Floor: Primary suite with a king bed, reading room and private bath.

Bedroom Four - Main House, Second Floor: Two twin beds, shared bath.

Bedroom Five - Main House, Second Floor: Two twin beds, shared bath.

Bedroom Six - Guest House, First Floor: Queen bed with private bath.

Bedroom Seven - Guest House, Second Floor: Twin bed, shared bath.

Bedroom Eight - Guest House, Second Floor: Two twin beds, shared bath.

OysterNest accommodates up to 15 guests across 8 bedrooms, with 6 full and 2 half baths, and is fully furnished for an easy, relaxed island stay.

Note: We always recommend making every effort to personally view a property before booking. We represent the condition, size, and location of each home as accurately as possible, although all information is deemed reliable but not guaranteed. As rental agents, we represent the landlord. Please also be aware that any home built prior to 1978 may contain lead paint. Various types of mold occur naturally on Martha’s Vineyard, and some individuals may be sensitive or have allergic reactions to them.