645 S Orleans Rd
$2,700,000
7
Beds
6/1
Baths
3,549
Sqft
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$2,700,000
7
Beds
6/1
Baths
3,549
Living Area
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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.
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Highlights
- Cooling: Window Unit(s)
- Heating: Baseboard
- Property Class: Residential
- Style: Antique
- Year Built: 1930
- Has View: Yes
- Parking Spots: 4
- Property Type: Single Family Residence
- Total Rooms: 12
- Status: Active
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Additional Details
- Fireplaces: 2
- SqFt Source: Public Record
- Year Built Details: Approximate
- Zoning: 96-23-0
- Foundation: Block
- View: Scenic View(s)
- Year Built Source: Public Records
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Amenities
- Waerfront: Yes
- Waterfront Features: Waterfront, Ocean, Bay, Harbor, Dock/Mooring, Frontage, Deep Water Access, Direct Access, Private, Beach Access, Bay, Harbor, Direct Access, Frontage, 0 to 1/10 Mile To Beach
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Utilities
- Sewer: Private Sewer
- Water Source: Public
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Fees / Taxes
- Assessed Value: $1,757,800
- Taxes: $10,740
- Tax Year: 2026
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 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.