An extraordinary waterfront estate on Menemsha Pond, this world-class compound offers an unparalleled luxury rental experience in the heart of Chilmark. Designed for elevated coastal living, the property seamlessly blends sophisticated architecture, resort-style amenities, and breathtaking panoramic water views across an exceptional multi-structure retreat.

The main residence features six beautifully appointed ensuite bedrooms, highlighted by a spectacular first-floor primary suite with dual spa-inspired bathrooms. Thoughtfully designed for both grand entertaining and intimate relaxation, the home offers expansive indoor and outdoor living spaces, a state-of-the-art theater with massage seating, and two designer kitchens outfitted with premium appliances for a truly elevated culinary experience.

Overlooking the water, the expansive waterfront entertaining terrace is designed to host on a remarkable scale. Italian outdoor furnishings accommodate up to 20 guests, while a stunning dining table seats 24 for unforgettable al fresco evenings. Additional outdoor features include a built-in Kalamazoo grill and pizza oven, handcrafted wooden bar, custom stone fire pit, and oversized Tuuci umbrellas—all framed by the beauty of Menemsha Pond.

The resort-style pool house is a private wellness sanctuary featuring an indoor heated 10’ x 30’ pool and spa surrounded by dramatic floor-to-ceiling retractable glass walls that create a seamless indoor-outdoor experience. Additional amenities include a sauna, steam room, wet bar, guest suite, and an expansive second-floor guest residence complete with a spacious bedroom, living room, laundry, and two private balconies.

Perched above the estate, a secluded writer’s cottage captures sweeping hilltop views over the pond, offering an inspiring and tranquil retreat.

Designed with recreation and entertainment in mind, the property also includes a dedicated entertainment pavilion featuring a fully equipped luxury gym with Technogym and Peloton equipment, floor-to-ceiling windows, and an indoor basketball court with an NBA-caliber professional shooting machine. Below, a six-car garage includes Porsche and Tesla charging stations.

Outdoor amenities continue with a tennis court lined for pickleball, a large cedar jungle gym, and a private 115-foot deep-water dock complete with a boathouse and an impressive collection of waterfront equipment including paddleboards, kayaks, wetsuits, and more.

For guests seeking the ultimate on-the-water experience, three custom boats are available for use during your stay:

• A 55-foot custom Italian Novamarine BS160 with five Mercury Racing outboard engines (captain required)
• A MasterCraft X26 designed for wake surfing, water skiing, and wakeboarding with customizable wave technology
• A Zodiac Open 7.0 speed boat powered by a Yamaha 200 HP engine, ideal for coastal cruising and watersports

Located moments from the beaches and the iconic fishing village of Menemsha, guests can enjoy renowned seafood, local markets, art fairs, boating, and some of Martha’s Vineyard’s most spectacular sunsets. From nearly every vantage point on the property, sweeping sunset views over Menemsha Pond create an atmosphere of absolute serenity and coastal sophistication.

This exceptional estate presents a rare opportunity to experience Martha’s Vineyard at the highest level—where privacy, luxury, wellness, and waterfront living come together in one unforgettable destination.