645 S Orleans Road, Orleans, MA 02653 (MLS # 22502226)
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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.
| DAYS ON MARKET | 22 | LAST UPDATED | 5/12/2025 |
|---|---|---|---|
| YEAR BUILT | 1945 | COUNTY | Barnstable |
| STATUS | Active | PROPERTY TYPE(S) | Single Family |
| ADDITIONAL DETAILS | |
| AIR | None |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Electric Water Heater |
| BASEMENT | Crawl Space, Partial, Yes |
| EXTERIOR | Garden |
| FIREPLACE | Yes |
| HEAT | Hot Water |
| LOT | 0.25 acre(s) |
| LOT DESCRIPTION | Waterfront |
| SEWER | Private Sewer |
| STORIES | 2 |
| TAXES | 10215 |
| WATER ACCESS | Little Pleasant Bay |
| WATERFRONT | Yes |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listed with Berkshire Hathaway HomeServices Robert Paul Properties
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