This exceptional waterfront estate offers unmatched panoramic views from house and guest house with extraordinary privacy on a nearly two acre setting rarely found in this coveted Oak Bluffs location. Commanding sweeping vistas of Lagoon Pond, Vineyard Haven, Hines Point, the iconic drawbridge, Vineyard Sound, and even distant views of Cape Cod. The property includes a renovated three-bedroom main residence and a two-bedroom guest house, each thoughtfully oriented to capture the ever changing light over the water. The main home offers a spacious open layout with generous living, dining, and sitting areas, ideally suited for entertaining and family gatherings and all with stunning views of the water. A large, bright kitchen serves as the heart of the home, while the living room, dining room, primary bedroom and two elevated decks provide front row seats to boating activity, wildlife, and some of the most spectacular sunsets on the island. The primary bedroom is a serene sanctuary with floor to ceiling water views that feel truly immersive. A second main level bedroom also has water views and its own full bath. On the lower level, a bedroom suite includes a comfortable sitting area with a TV, and spacious full bath. The guest house is a retreat unto itself, offering equally stunning water views from kitchen, living room and private porch. Its large primary bedroom features ample space, while the additional bedroom is a cozy, private nook. Outdoors, the estate's expansive grounds offer a rare combination of beauty, privacy, and direct waterfront access. Private steps lead to the property's own sandy beach and mooring, where guests can enjoy swimming, boating, kayaking, paddle boarding, fishing, or simply savor the extraordinary natural beauty. An amazing variety of birds, including osprey complete the scene out on the water. The property also borders 14 acres of conservation land with scenic walking trails, enhancing the sense of seclusion, privacy and connection to nature. This is a truly remarkable island estate that has had only 3 owners in the past 65 years. This is a generational opportunity to enjoy and improve this family compound with unforgettable views, refined living spaces and unparalleled waterfront setting.