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$2,150,000

22 Winslow Drive, Orleans MA 02653
Orleans, MA 02653
Listed by Whitaker Group Cape Cod
Bedrooms
5
Bathrooms
5
Living area
4,091 sqft
Year built
1968

About this home

Overlooking a tranquil pond, 22 Winslow Drive offers a peaceful setting with a strong sense of privacy. Birds move easily through the surrounding landscape, and the quiet setting creates a calm and natural atmosphere. This gracious Cape Cod home has been cherished by four generations. Thoughtfully expanded over the years while preserving its warmth and character. Inside, more than 4,000 square feet of living space unfolds with a comfortable and natural flow. Hardwood floors, exposed beams, fireplaces, and generous gathering spaces create a welcoming environment for everyday living. A flexible fifth room within the home can be privately sectioned off and features its own exterior entrance, full bathroom, and kitchenette. The home has been carefully maintained and thoughtfully updated, including a generator for year-round living. Finished space above the carriage house provides additional options for work or hobbies. Located just moments from Pleasant Bay.

Highlights

WaterfrontFireplace

Property details

MLS #
73489022
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
154
On market date
March 19, 2026
Stories
N/A
Garage spaces
2
Lot size
0.8 acres
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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Orleans Elementary
3.04 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
2.28 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
4.49 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
$13,098/mo
$430,000 down
$1,720,000 loan
Principal & interest$11,156
Property tax (est.)$1,792
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated June 17, 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.