22 Winslow Drive
Orleans, MA, 02653
$2,150,000
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.
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.
Current real estate data for Single Family in Orleans as of Aug 16, 2026
47
Single Family Listed
120
Avg DOM
746
Avg $ / SqFt
$2,318,508
Avg List Price
Property Details
Price:
$2,150,000
MLS #:
22600770
Status:
Pending
Beds:
5
Baths:
5
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
orleans
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
Schools
Interior
Appliances
Dishwasher, Electric Range, Refrigerator, Washer, Electric, Water Heater
Bathrooms
5 Full Bathrooms
Cooling
Central Air
Fireplaces Total
3
Flooring
Wood
Interior Features
Attic Storage, Recessed Lighting
Laundry Features
Electric Dryer, Laundry Room
Exterior
Construction Materials
Clapboard
Exterior Features
Outdoor Shower, Underground Sprinkler System
Garage Spaces
2
Parking Features
Detached, Garage Door Opener, Driveway, Paved
Parking Spots
6
Parking Total
6
Patio And Porch Features
Deck
Roof
Asphalt, Pitched
Stories
2
Waterfront Features
Waterview, Waterfront, Lake/Pond
Financial
Tax Year
2025
Taxes
$9,487
Map
Contact Us
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Community
- Address22 Winslow Drive Orleans MA
- CityOrleans
- CountyBarnstable
- Zip Code02653
Subdivisions in Orleans
Property Summary
- 22 Winslow Drive Orleans MA is a Single Family for sale in Orleans, MA, 02653. It is listed for $2,150,000 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 $526. The average price per square foot for Single Family listings in Orleans is $746. The average listing price for Single Family in Orleans is $2,318,508. To schedule a showing of MLS#22600770 at 22 Winslow Drive in Orleans, MA, contact your Thomas D Brown R E Associates agent at 508-487-1112.
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Raised in Orleans and now a resident of Truro, Lucy is extremely familiar with life on the Outer Cape. She is experienced in real estate sales on Cape Cod and has been involved in construction, development and real estate for over thirty-five years here on the Outer Cape. She presently handles all facets of marketing for both Brown Associates and Cape Vacation Rentals. Degree in Sales & Marketing; formerly associated with Nickerson Realty Corp. where she handled all phases of land development, a…
More About Lucy
22 Winslow Drive
Orleans, MA