Active
645 S Orleans
Orleans, MA 02653
Residential · Active · MLS #73373131
Listing Courtesy of Berkshire Hathaway HomeServices Robert Paul Properties | Guthrie Schofield Group
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MLS PIN data
About this home
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.
Property information
Details at a glance
Interior
- Rooms
- 12
- Heating
- Baseboard
- Cooling
- Window Unit(s)
- Fireplaces
- 2
Building
- Style
- Single Family Residence
- Year built
- 1930
- Parking
- 4
- Foundation
- Block
Land & utilities
- Lot size
- 0.25 acres
- Water
- Public
- Sewer
- Private Sewer
- Waterfront
- Y
- Zoning
- 96-23-0
Financial
- Annual taxes
- $10,740
- Assessment year
- 2026
Listing history
Price and status timeline
- Exp
$2,995,000 · Sep 26, 2024
Property value estimate
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Comparable sales
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Local market context
How this home compares in Orleans
Active city listing statistics from MLS PIN as of September 6, 2026. Asking prices are not completed-sale values.
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Common questions
About 645 S Orleans
Can I schedule a private showing?
Yes. Request a tour of 645 S Orleans and a Bean Group agent will help coordinate an available time with the listing side.
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Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.
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