For the first time in generations, this extraordinary Pleasant Bay compound – featuring the iconic Topside main residence and the charming two-bedroom Boathouse – is offered as a rare legacy estate. With a deep-water dock, moorings, and direct bay access, it delivers a front-row seat to the rhythms of Pleasant Bay and boundless recreation. Both homes enjoy 270-degree views across the water to Eastward Ho, the Chatham Yacht Club, and the Atlantic beyond. Topside offers 5 bedrooms and 4.5 baths with timeless coastal charm and inviting gathering spaces. The Boathouse, perched just above the shoreline, features 2 bedrooms, 1 bath, and a private deck for quiet moments by the sea. A secluded garden patio and broad waterfront lawn complete the experience. With strong rental history and exceptional potential for personalization or expansion, this lifestyle property invites multigenerational enjoyment, investment, or retreat – an iconic opportunity in one of Cape Cods most storied settings.