View a Virtual Tour of 645 Orleans Road, Orleans, MA645 Orleans Road, Orleans, MA
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 waterfront estate. With a deep-water dock, moorings, and direct access to the bay, the property delivers a front-row seat to the rhythms of Pleasant Bay and boundless recreation potential. Both homes enjoy sweeping 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 character and spaces designed for gathering, while the ''Boathouse'' sits just above the shoreline, featuring 2 bedrooms, 1 bathroom, and its own deck for quiet moments by the sea. A secluded garden patio and broad waterfront lawn offer a blend of intimacy and scale. With a strong rental history and immense potential for expansion or personalization, this is a lifestyle property that invites multigenerational living, savvy investment, or a private retreat. A once-in-a-lifetime opportunity to own one of Cape Cod's most storied waterfront settings.
645 Orleans Road, Orleans, MA
Listing Courtest of:
Berkshire Hathaway HomeServices Robert Paul Properties
Listing Agent: Guthrie Schofield Group (774-487-8554)
Listing provided courtesy of Berkshire Hathaway HomeServices Robert Paul Properties
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This site was last updated 06/18/2026. All properties are subject to prior sale, changes, or withdrawal.
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