Extraordinary contemporary waterfront estate in Chilmark

A rare offering on the shores of Menemsha Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Thoughtfully designed with striking modern architecture, walls of glass, and seamless indoor-outdoor living, this one-of-a-kind compound captures breathtaking water views from nearly every room. Set on 4.9 acres with a private 115-foot deep-water dock, the property represents an irreplaceable opportunity, as a waterfront estate of this scale and caliber could no longer be replicated today. The main residence features six luxurious ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired bathrooms. Two state-of-the-art kitchens appointed with top-tier appliances provide exceptional spaces for entertaining, while the dramatic main living area showcases soaring cathedral ceilings and panoramic pond views. A screened porch and expansive waterfront deck create effortless transitions between interior and exterior living spaces. Upstairs, a striking glass-lined hallway with a dramatic glass floor overlooks the water, leading to guest suites with private baths and access to a second-floor deck. Exceptional amenities include a private theater with massage seating, wine cellar, outdoor shower, and a hilltop writer’s cottage with sweeping waterviews. Set just beyond the main house is the pool house. The pool house is a private wellness retreat featuring a heated indoor pool, spa, sauna, cold plunge, steam room, wet bar, and spacious enclosed porch surrounded by retractable glass doors. The second floor includes a full guest suite with a bedroom, living room, laundry, and dual balconies overlooking Menemsha pond. The estate also includes an impressive 1,927 sq. ft. barn-style entertainment pavilion designed to complement the property’s contemporary aesthetic while offering exceptional recreational amenities. The upper level features a professionally designed fitness center with floor-to-ceiling windows overlooking the grounds and pond, alongside a sprawling recreation lounge with space for indoor basketball, billiards, ping pong, and additional sporting activities. Below, the structure houses an expansive six-car garage, ideal for luxury vehicle storage, boating equipment, and recreational gear. Completing this incomparable estate are a private tennis court and charming boathouse by the dock for paddleboards and waterfront equipment. An unparalleled modern retreat in one of Martha’s Vineyard’s most exclusive waterfront settings.