22 Winslow Drive
Orleans, MA, 02653
$2,300,000
5 Beds
5 Baths
4,091 SqFt
0.8 Acres
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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. This property offers convenient access to many of the Lower Cape’s most loved destinations while maintaining a peaceful residential setting.

Property Details

Price:
$2,300,000
MLS #:
22600770
Status:
Active
Beds:
5
Baths:
5
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
southorleans
Listed Date:
Mar 16, 2026
Finished Sq Ft:
4,091
Total Sq Ft:
4,091
Lot Size:
34,848 sqft / 0.80 acres (approx)
Year Built:
1968
Cape CodWaterfrontSouth OrleansSouthorleansNausetUncle Seth’s Pond

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Schools

School District:
Nauset

Interior

Appliances
Dishwasher, Washer, Refrigerator, Electric Range, Electric Dryer, Electric Water Heater
Bathrooms
5 Full Bathrooms
Cooling
Central Air
Fireplaces Total
3
Flooring
Wood
Interior Features
Recessed Lighting
Laundry Features
Laundry Room, First Floor

Exterior

Architectural Style
Cape Cod
Construction Materials
Clapboard
Exterior Features
Outdoor Shower
Garage Spaces
2
Open Parking YN
1
Parking Spots
6
Parking Total
6
Patio And Porch Features
Deck
Roof
Asphalt, Pitched
Stories
2
Window Features
Bay/Bow Windows

Financial

Tax Year
2025
Taxes
$9,487

Map

Community

Market Summary

Current real estate data for Single Family in Orleans as of May 13, 2026
43
Single Family Listed
160
Avg DOM
704
Avg $ / SqFt
$2,350,993
Avg List Price

Property Summary

    22 Winslow Drive Orleans MA is a Single Family for sale in Orleans, MA, 02653. It is listed for $2,300,000 and features 5 beds, 5 baths, and has approximately 4,091 square feet of living space, and was originally constructed in 1968. The current price per square foot is $562. The average price per square foot for Single Family listings in Orleans is $704. The average listing price for Single Family in Orleans is $2,350,993. To schedule a showing of MLS#22600770 at 22 Winslow Drive in Orleans, MA, contact your Pleasant Bay Realty agent at (774) 209-1428.

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22 Winslow Drive
Orleans, MA