For sale
  • $3,950,000

    645 S Orleans Road, Orleans, MA 02653

    7beds
    3,548sqft
    : 
    Single Family Residence
    Built in 1945
    0.25 Acres Lot
    $-- Zestimate®
    $1,113/sqft
    $-- HOA

    What's special

    Broad waterfront lawnDeep-water dockTimeless coastal characterSecluded garden patioSpaces designed for gathering
    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.
    106 days
    on Zillow
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    1,020
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