Aquinnah Hilltop Estate with Heated Pool and Ocean Views

Set high above the Vineyard’s western edge, Windy Hill is a private Aquinnah estate with sunrises, spectacular sunsets, and sweeping views across the Elizabeth Islands, Menemsha Bight, and the Atlantic beyond. With a newly renovated interior and high-end design throughout, this compound blends natural beauty with effortless luxury.

The estate consists of a 4-bedroom, 4.5-bathroom Main House and a 2-bedroom, 1.5-bathroom Guest House, offering space, privacy, and comfort for larger groups or multi-generational stays.

Enjoy slow mornings and golden hour cocktails from multiple decks and patios, take a dip in the heated pool, play bocce, or head down the path to the secluded South Shore beach just minutes away. The Guest House features a screened-in porch, and the entire property has central AC and heat.

Main House (4BR, 4.5BA): King bedroom (ensuite, first floor); King primary suite (ensuite, second floor); Queen bedroom (ensuite, second floor); Queen bedroom (ensuite, lower level); half bath off the main living area
Guest House (2BR, 1.5BA): King bedroom (ensuite); Queen bedroom with private outdoor shower and half bath

Features: heated pool, bocce court, screened-in porch at the Guest House, multiple view decks and patios, central AC and heat, steps to private South Shore beach access.

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.