645 S Orleans Rd, Orleans, MA 02653 (MLS # 73373131)
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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 estate. With a deep-water dock, moorings, and direct bay access, it delivers a front-row seat to the rhythms of Pleasant Bay and boundless recreation. Both homes enjoy 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 charm and inviting gathering spaces. The "Boathouse," perched just above the shoreline, features 2 bedrooms, 1 bath, and a private deck for quiet moments by the sea. A secluded garden patio and broad waterfront lawn complete the experience. With strong rental history and exceptional potential for personalization or expansion, this lifestyle property invites multigenerational enjoyment, investment, or retreat"”an iconic opportunity in one of Cape Cod's most storied settings.
| LAST UPDATED | 9/8/2025 | 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 - Today | $3,495,000 |
| ADDITIONAL DETAILS | |
| AIR | Window Unit(s) |
|---|---|
| AIR CONDITIONING | Yes |
| FIREPLACE | Yes |
| HEAT | Baseboard |
| LOT | 0.25 acre(s) |
| SEWER | Private Sewer |
| STYLE | Antique |
| TAXES | 9500 |
| VIEW | Yes |
| VIEW DESCRIPTION | Scenic |
| WATER | Public |
| WATERFRONT | Yes |
| WATERFRONT DESCRIPTION | Ocean Front, Waterfront, Beach Access |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listing provided by Guthrie Schofield Group, Berkshire Hathaway HomeServices Robert Paul Properties
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