Two homes on over three acres of waterfront on the beautiful and coveted Tisbury Great Pond. This remarkable waterfront property offers a rare opportunity to own a serene compound with two existing homes and a private permitted dock. Both the main house and guest house boast unobstructed water views, creating a tranquil and picturesque setting perfect for birdwatching, relaxation, and year-round enjoyment. The main house features four bedrooms, two and a half bathrooms, central air conditioning, screened porch for stunning sunset views, den/sunroom with wet bar plus a spacious unfinished basement. The guest house provides an additional two bedrooms, two bathrooms and has its own separate three-bedroom septic system. The guest house has been recently updated with new roof, windows, and cedar shingle siding. Additional highlights for this property include a permitted dock for direct pond access and further access to the South shore beaches. There is no waiting period to add a pool, barn, or expand on the 3 acre property-unlike in nearby Chilmark. This central location with close proximity to both West Tisbury village and all island towns, offers a perfect blend of up-island privacy with down-island convenience. This is a rare opportunity to move in immediately, renovate to your taste, or rebuild over time-all while enjoying the best of Martha's Vineyard living in an exceptional natural setting.