INNOVATE
Real Estate
No photos available for this listing

$2,700,000

645 S Orleans, Orleans MA 02653
Orleans, MA 02653
Listed by Guthrie Schofield Group
Bedrooms
7
Bathrooms
6.1
Living area
3,549 sqft
Year built
1930

About this home

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.

Highlights

WaterfrontViewFireplace

Property details

MLS #
73373131
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
N/A
On market date
N/A
Stories
N/A
Garage spaces
N/A
Lot size
0.25 acres

Location

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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Orleans Elementary
3.41 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
164
Student:teacher ratio
8.2:1
District
Orleans
MiddleCharter
Cape Cod Lighthouse Charter School
2.2 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
250
Student:teacher ratio
13.9:1
District
Cape Cod Lighthouse Charter (District)
High
Cape Cod Region Vocational Technical
4.58 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
654
Student:teacher ratio
9.8:1
District
Cape Cod Regional Vocational Technical

Mortgage calculator

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Est. monthly payment
$16,410/mo
$540,000 down
$2,160,000 loan
Principal & interest$14,010
Property tax (est.)$2,250
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated May 16, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.