Martha’s Vineyard’s priciest listing has just hit the market for $19.5 million.

Tucked away on a peninsula in the island’s only gated community is the stuff of coastal New England dreams: a 3,786-square-foot, five-bedroom, ridge-top home.

“It’s quite a spectacular property, set on 6.2 acres that directly abuts 18 acres,” says listing agent Grace Hagerty, of Grace Hagerty Real Estate Inc. “It is also one of 11 homes on 550 acres of deeded conservation land that can’t be expanded.”

Like ‘entering a different country’

The Chilmark, MA, property’s serene locale enjoys private access to more than 2 miles of sandy beaches.

“There are miles and miles of trails to walk along, with 2.5 miles of private beach and dunes on the south shore of the island,” Hagerty says. “It is one of the nicest beaches on the East Coast. There is also 1 mile of Squibnocket Pond frontage. It’s an extremely private lot.”

And all the surrounding acreage offers a worlds-away vibe. Hagerty likens it to “entering a different country.” With 360-degree water views, the home is a tranquil retreat—with the potential for more accommodations.

“Although it can’t be subdivided, there is room for expansion,” she says. “It’s so rare for a property to come up for sale like this. It’s a gorgeous lot of land, and the property is very high, so it has these incredible views all around.”

Hagerty adds that the property is in the island’s only “pesticide-free zone,” which allows for abundant natural delights.

“There are all kinds of birds, fauna, flora, and beehives,” she says. “It’s just an amazing property. It really could almost be a national park, because the grounds are so spectacular.”

The place even includes a sheep farm; a barn with lofts; and a mobile, cedar chicken coop that “houses award-winning French Bresse chickens,” according to the listing.

Updated abode

Built in 2000, the residence recently underwent an exterior face-lift. Updates include cedar-shake shingles, mahogany trim, and copper gutters. Rooftop solar panels are another addition.

The spacious living room has a cathedral ceiling; exposed beams; cherry-wood floors; and a cozy, brick fireplace.

The light-filled kitchen soars in height, with custom cabinetry, high-end appliances, stone countertops, and a walk-in pantry.
A first-floor primary suite leads to a mahogany, outdoor shower from the bathroom. A second outdoor shower is designed for guests.

Designed for entertaining, the house boasts a mahogany deck with a screened porch and fireplace.

“The home has been incredibly well maintained and it has been winterized, so it could be used as a primary residence. But most people looking at it are wanting to use it as a summer home,” Hagerty says. “I think the next buyer will be somebody who loves the outdoors, peace, and privacy and wants to be away from everybody.”

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