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Single Family Residence at 645 S Orleans, Orleans MA 02653, Orleans
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$2,700,000

645 S Orleans, Orleans MA 02653
Orleans, MA 02653
Listed by Guthrie Schofield Group
Bedrooms
7
Bathrooms
6.5
Living area
3,549 sqft
Year built
1930

About this home

For the first time in generations, this landmark Pleasant Bay compound—anchored by the iconic "Topside" main residence and the charming two-bedroom "Boathouse"—is offered as a rare, generational waterfront estate, a site long cherished by those who have called it home. 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. Both homes enjoy sweeping 270-degree views across the water to Eastward Ho, the Chatham Yacht Club, and the Atlantic beyond. Thoughtfully sited by its original architect to capture the light and water at every turn, "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 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, landmark waterfront settings.

Highlights

WaterfrontViewFireplace

Property details

MLS #
73373131
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
514
On market date
May 12, 2025
Stories
N/A
Total bathrooms
6.5
Garage spaces
N/A
Parking spaces
4
Lot size
0.25 acres

Location

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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

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

Walkability

Blended score for Orleans's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

25
Car-dependent
out of 100
EPA National Walkability Index
6.3 / 20 -- Below average walkable
Google Places amenity density
15 / 100
Restaurants & cafes0
Grocery stores0
Parks5
Schools0
Transit stops0
Pharmacies0

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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/mo
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 July 21, 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.