Price Reduced 11.52%

$3,495,000 ($984.78 per sqft)

Est. Mortgage $16,539/mo *

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645 S Orleans, Orleans, MA, 02653

645 S Orleans, Orleans, MA, 02653
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12 rooms

7 beds

6 Full / 1 Half baths

1930

Antique

3,549 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 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.

Status:

Active

Type:

Single-family residential

Zoning:

96-23-0

Heating:

Baseboard

Cooling:

Window Unit(s)

Parking:

4-car

Acreage:

0.25

Est. Taxes:

$9,500

Assessment

$1,552,300

View Description:

Scenic View(s)

Waterfront:

Yes

MLS #:

73373131

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 508-945-5553