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.
Property Details
Price:
$3,950,000
MLS #:
22502226
Status:
Active
Beds:
7
Baths:
6.5
Address:
645 S Road Orleans
Type:
Single Family
Subtype:
Single Family Residence
City:
Orleans
Listed Date:
May 12, 2025
State:
MA
Finished Sq Ft:
3,548
Total Sq Ft:
3,548
ZIP:
02653
Lot Size:
10,890 sqft / 0.25 acres (approx)
Year Built:
1945
Schools
School District:
Nauset
Interior
Appliances
Electric Water Heater
Bathrooms
6 Full Bathrooms, 1 Half Bathroom
Cooling
None
Flooring
Wood, Tile
Heating
Hot Water
Exterior
Exterior Features
Garden
Roof
Asphalt
Financial
Tax Year
2025
Taxes
$10,215
Map
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As a lifelong resident of the outer Cape I was the third generation to pick up the mantel in the family construction business. In my early twenties, I called the Cape my home on weekends as I spent several years working for a variety of off-Cape commercial construction companies. My commercial site supervision resume includes two supermarkets, two HUD projects, a funeral home and a handful of steel industrial buildings as well as various restaurant and office remodels. Prior to striking out on m…
More About Jon
645 S Road Orleans
Orleans, MA
LIGHTBOX-IMAGES
As a lifelong resident of the outer Cape I was the third generation to pick up the mantel in the family construction business. In my early twenties, I called the Cape my home on weekends as I spent several years working for a variety of off-Cape commercial construction companies. My site supervision resume includes two supermarkets, two HUD projects, a funeral home and a handful of steel industrial buildings as well as various restaurant and office remodels.