Menemsha Pond Waterfront Compound with Indoor Pool and Deep Water Dock

A rare waterfront compound on Menemsha Pond, built for guests who want space, privacy, and genuine top-tier amenities in one of Chilmark's most beautiful settings.

The main house holds six ensuite bedrooms, anchored by a first-floor primary suite with two full bathrooms. Two fully equipped kitchens with high-end appliances handle everything from a quiet morning coffee to cooking for a full house. A home theater with massage chairs rounds out the indoor living, and the water views carry through nearly every room. Outside, a large waterfront deck features seating for twenty and a dining table for twenty-four, plus a built-in Kalamazoo grill and pizza oven, a wooden bar, a stone fire pit, and two oversized umbrellas. The second floor is its own full guest suite with a large bedroom, living room, washer and dryer, and two spacious balconies.

The pool house is the relaxation hub: an indoor heated 10 by 30 foot pool and spa wrapped in floor-to-ceiling sliding glass. It also includes a sauna, steam room, wet bar, and guest bedroom. Up the hill, a writer's cottage offers panoramic views across the pond.

A separate entertainment building houses a full gym with Technogym and Peloton equipment alongside an indoor basketball court with an NBA-grade shooting machine. Below is a six-car garage with EV charging. For outdoor play, there is a tennis court lined for pickleball and a large cedar jungle gym.

On the water, a 115 foot deep-water dock and boat house come stocked with paddleboards, kayaks, and wetsuits. Three boats are available to add to your stay: a 55 foot Novamarine BS160 (captain required), a Mastercraft X26 for skiing, wakeboarding and wake surfing, and a 26 foot Zodiac Open 7.0.

Menemsha is a working fishing village known for its harbor, fresh seafood, and famous sunsets, which settle over the pond right from the property.

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.