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 Italian 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 Tucci 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 that opens the space to the outdoors. 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 outfitted with Technogym and Peloton cardio and weight equipment, framed by floor-to-ceiling windows, alongside an indoor basketball court with an NBA-grade shooting machine. Below is a six-car garage with Porsche and Tesla charging stations. 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, and guests can take one, two, or all three:
Boat One is a 55 foot Novamarine BS160, custom built in Italy with five Mercury Racing outboards and extensive customization. A captain is required.
Boat Two is a Mastercraft X26 built for water skiing, wakeboarding, and wake surfing, with a touchscreen panel to dial in a custom surf wave.
Boat Three is a 26 foot Zodiac Open 7.0 powered by a Yamaha 200 HP outboard, agile enough for skiing and stable enough for open ocean.
Menemsha itself is a working fishing village known for its harbor, fresh seafood, and the sunsets that draw a crowd to the beach most clear evenings. From the property, those same sunsets settle over the pond, the sky turning warm and the water going still. Nearby beaches are made for swimming and long afternoons in the sun, and the island calendar stays full with farmers' markets, art fairs, and community events all season.
This is a high-end escape in the truest sense, a place to slow down, spread out, and enjoy a property where every detail was clearly considered.
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.