Property Details: MLS #22502226
| 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. | |
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Price: $3,950,000 | Bedrooms: 7 | Bathrooms: 6/1 645 Orleans Road, Orleans, MA 02653 |
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Courtesy of Orleans Village Properties, LLC. All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Orleans Village Properties, LLC include the name of the listing broker. Neither the listing company nor Orleans Village Properties, LLC shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Orleans Village Properties, LLC has chosen to display only certain towns and/or types or styles of properties. Copyright 2002 - 2025 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.
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This site was last updated May 12, 2025 at 4:20:05 PM EDT. All properties are subject to prior sale, changes, or withdrawal. Orleans Village Properties, LLC has chosen to display only certain towns and/or types or styles of properties. This site may not show all listings that are available through the Cape Cod & Islands Multiple Listing Service, Inc. |
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Orleans Village Properties, LLC220 Main Street
PO Box 1551
East Orleans, MA 02643
Call: 508-255-1700
Text: 508-254-8001
