$2,300,000
22 Winslow Drive
Orleans, MA, 02653
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.
Property Details
Price:
$2,300,000
MLS #:
73489022
Status:
Active
Beds:
5
Baths:
5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Mar 19, 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
Above Grade Finished Area
4091
Bathrooms
5 Full Bathrooms
Cooling
Central Air, Heat Pump
Fireplaces Total
3
Heating
Forced Air, Heat Pump, Electric
Exterior
Architectural Style
Cape
Covered Spaces
2
Garage Spaces
2
Lot Features
Sloped
Open Parking Spaces
6
Parking Features
Detached
Parking Spots
8
Parking Total
8
Waterfront Features
Waterfront, Pond, 1/2 to 1 Mile To Beach
Financial
Tax Year
2025
Taxes
$9,487
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Single Family in Orleans as of May 04, 2026
36
Single Family Listed
156
Avg DOM
707
Avg $ / SqFt
$2,224,075
Avg List Price
Community
- Address22 Winslow Drive Orleans MA
- CityOrleans
- CountyBarnstable
- Zip Code02653
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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 $707. The average listing price for Single Family in Orleans is $2,224,075. To schedule a showing of MLS#73489022 at 22 Winslow Drive in Orleans, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Gibson Sotheby’s International Realty. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
22 Winslow Drive
Orleans, MA