Boston Luxury Condos and Apartments
355 Boylston St / (617) 233-5800

645 S Orleans Rd

Orleans, MA ID #73373131

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645 S Orleans Rd

- Orleans, MA ID #73373131

Property Description

For the first time in generations, this landmark Pleasant Bay compound—anchored by the iconic "Topside" main residence and the charming two-bedroom "Boathouse"—is offered as a rare, generational waterfront estate, a site long cherished by those who have called it home. 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. Both homes enjoy sweeping 270-degree views across the water to Eastward Ho, the Chatham Yacht Club, and the Atlantic beyond. Thoughtfully sited by its original architect to capture the light and water at every turn, "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 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, landmark waterfront settings.

Additional Details

  • Status: ACT
  • Type: Single Family, Single Family Residence
  • Zip Code: 02653
  • Taxes: 10,740
  • Acres: 0.25

Parking

  • Garage Capacity: 4
  • Parking Spaces: 4

Rooms/Dimensions

  • Total Rooms: 12

Location

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645 S Orleans Rd, Orleans, MA

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Content © 2026 MLS Property Information Network, Inc.
The information in this listing was gathered from third party resources including the seller and public records. Listing information provided courtesy of Guthrie Schofield Group of Berkshire Hathaway HomeServices Robert Paul Properties. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations or warranties as to the accuracy of this information.