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645 S Orleans RoadOrleans, MA 02653Price: $3,950,000

  • Price: $3,950,000
  • Est. Mortgage of $/month
  • 37 Days on Market
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Federal 30-year interest rate: 6.84% last updated on Jun 12, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $3,950,000List Price
  • 7Bedrooms
  • 7Bathrooms
  • 0.25Acreage
  • 3,548Square Feet

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645 S Orleans Road Orleans MA

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Listed by Guthrie Schofield Group of Berkshire Hathaway HomeServices Robert Paul Properties
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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broker reciprocity The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Coldwell Banker Martha Murray Real Estate are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Coldwell Banker Martha Murray Real Estate shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

This site was last updated June 17, 2025 5:52 PM EDT. All properties are subject to prior sale, changes, or withdrawal.

Coldwell Banker Martha Murray Real Estate 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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