$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
Address:
22 Winslow Drive
Type:
Single Family
Subtype:
Single Family Residence
City:
Orleans
Listed Date:
Mar 19, 2026
State:
MA
Finished Sq Ft:
4,091
Total Sq Ft:
4,091
ZIP:
02653
Lot Size:
34,848 sqft / 0.80 acres (approx)
Year Built:
1968
Schools
Interior
Bathrooms
5 Full Bathrooms
Cooling
Central Air, Heat Pump
Fireplaces Total
3
Heating
Forced Air, Heat Pump, Electric
Exterior
Architectural Style
Cape
Parking Features
Detached
Parking Spots
8
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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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
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