$3,950,000

645 S Orleans Road , Orleans, MA 02653

 
Bedrooms:7 beds
Bathrooms:6 baths
Residential:3,548 sqft
Lot:0.25
Year Built:1945
Listing Status:Active

Listing Agent

Guthrie Schofield Group
Loan Amount:
Interest:
Term (Years):
Annual Tax:
Monthly Principal + Interest:$
Monthly tax: $
Total Payment:$

These amounts are estimates and do not take into consideration other expenses such as PMI, etc.. This is only an estimate.

Description

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.

Detailed Items

Other Information

645 S Orleans Road, Orleans, MA, 02653 is a residential listing of 3,548 sqft on a lot of 0.25. This residential listing has 7 bedrooms, and 6 baths. The map for this location can be viewed on Google maps at Google maps to property645 S Orleans Road, Orleans, MA
Copyright © 2025 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

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