New Listing - 05/12/2025

$3,950,000 ($1,113.30 per sqft)

Est. Mortgage $0/mo *

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645 S Orleans Road, Orleans, MA, 02653

645 S Orleans Road, Orleans, MA, 02653
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12 rooms

7 beds

6 Full / 1 Half baths

1945

3,548 sqft

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.

Status:

Active

Type:

Single-family residential

Zoning:

R

Heating:

Hot Water

Cooling:

None

Basement:

Bulkhead Access, Partial, Crawl Space

Levels:

2

Acreage:

0.25

Est. Taxes:

$10,215

Assessment

$1,637,100

Waterfront:

Yes

School District:

Nauset

Days on Market:

1

Appliances:

Electric Water Heater

MLS #:

22502226

Community Info

School Info

Walk Score

Mass Transit

Yelp

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Listing courtesy of Guthrie Schofield Group, Berkshire Hathaway HomeServices Robert Paul Properties Phone: 508-945-5553