luxury waterfront houses for sale Dukes County, United States

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.

Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature’s grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home’s timeless architecture and expansive front lawn make an unforgettable first impression. Inside, the home features a bright and airy open-concept layout that seamlessly blends the living, dining, and kitchen areas, all enhanced by the dramatic “big sky, big water” setting. Spanning three levels, the residence offers 4 bedrooms, 3 full bathrooms, and a spacious family room. Nearly every room captures breathtaking water views, creating a true connection to the surrounding coastal landscape. Step outside to the backyard lawn and follow the wooden boardwalk to your own private sandy beach. Whether launching a kayak or paddleboard for a day exploring Katama Bay, or taking a scenic shortcut to South Beach, this waterfront setting offers the very best of Vineyard living. Completing the property is a generous 2-car garage

WATERFRONT WITH DOCK – Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilities are endless. Enjoy water views from virtually every room as the home's spectacular waterfront setting seamlessly extends to your private sandy beach and deep-water dock, offering direct access for boating, swimming, paddle boarding, or simply relaxing by the water's edge. A truly special legacy property offered for the first time in over 50 years where history, charm, and an unparalleled waterfront lifestyle come together.

Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home for a client list that included Lady Diana Spencer. The historic main house has been completely modernized. There are 6 bedrooms spread out over almost 6000 square feet, a detached pool house, swimming pool, and Har-Tru tennis court. Wherever you are in this gracious home you will be blessed with sweeping views of the open fields, stone walls, and horses in the neighboring farm, a scene as if from a painting done in a previous century. Included within the 10 acres is a separate 3.3-acre parcel of land that will accommodate a full-size home. The property is part of the Tashmoo Farm Association which includes deeded access to the association dock on Lake Tashmoo and tennis courts.