A rare multi-generational waterfront estate in the heart of Osterville. Designed for gracious coastal living, the vaulted great room features a wood-burning fieldstone fireplace and floor-to-ceiling glass, capturing the panoramic views of Neck Pond and the Wianno Golf Course. The open kitchen, dining area, and three-season sunroom flow seamlessly to a wraparound deck for effortless indoor-outdoor living. The main residence includes four bedrooms and five baths, highlighted by a first-floor primary suite with a private deck and water views. The finished walk-out lower level offers a game room, wet bar, gym, and craft space. A 3 bay detached garage with guest quarters above accessed by a private elevator is ideal for hosting guests. Outdoor highlights include a bluestone terrace, pergola-covered hot tub, fire pit, and private dock. A heated garage, two generators, and expansive planting beds complete this resort-style retreat, just moments from Osterville s shops and restaurants.