645 S Orleans Rd, Orleans, MA 02653 (MLS # 73373131)
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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.
| LAST UPDATED | 5/16/2026 | YEAR BUILT | 1930 |
|---|---|---|---|
| COUNTY | Barnstable | STATUS | Active |
| PROPERTY TYPE(S) | Single Family |
| PRICE HISTORY | |
| Prior to Sep 4, '25 | $3,950,000 |
|---|---|
| Sep 4, '25 - Jan 31, '26 | $3,495,000 |
| Jan 31, '26 - Today | $2,700,000 |
| ADDITIONAL DETAILS | |
| AIR | Window Unit(s) |
|---|---|
| AIR CONDITIONING | Yes |
| FIREPLACE | Yes |
| HEAT | Baseboard |
| LOT | 0.25 acre(s) |
| LOT DESCRIPTION | Waterfront |
| SEWER | Private Sewer |
| STYLE | Antique |
| TAXES | 10740 |
| VIEW | Yes |
| VIEW DESCRIPTION | Scenic |
| WATER | Public |
| WATERFRONT | Yes |
| WATERFRONT DESCRIPTION | Ocean Front, Waterfront, Beach Access, Waterfront Access |
MORTGAGE CALCULATOR
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Listing provided by Guthrie Schofield Group, Berkshire Hathaway HomeServices Robert Paul Properties
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