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Properties

  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
  • 22 Winslow Drive, Orleans, Massachusetts, 5 Bedrooms Bedrooms, 11 Rooms Rooms,5 BathroomsBathrooms,Residential,For Sale,Winslow Drive,73489022
Property Description

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.

Features
Heating System:
Heat Pump, Forced Air, Electric
Cooling System:
Central Air, Heat Pump
Basement:
Full, Bulkhead, Interior Entry
Parking:
Detached
Sewer:
Private Sewer
Style:
Cape
Water:
Private, Public
Garage Parking:
2
Lead Paint:
Unknown
Waterview Features:
Pond
Additional Information
Parking Spaces:
8
Tax Year:
2025
Status:
Active
Price Per Sqft:
$562
Zoning:
R
Orig Price:
$2,300,000
Fireplaces:
3
Waterfront:
Yes
MlsStatus:
New
Address Map
City:
Orleans
State:
MA
County:
Barnstable
Postal Code:
02653
Longitude:
W70° 0' 13.6''
Latitude:
N41° 44' 13.3''
  • Google Map

Residential

22 Winslow Drive, Orleans, Massachusetts

5 Bedrooms
5 Total Bathrooms
4,091 Sqft
$2,300,000
Listing ID #73489022
Basic Details
Property Type :
Residential
Listing Type :
For Sale
Price :
$2,300,000
Bedrooms :
5
Rooms :
11
Total Bathrooms :
5
Full Bathrooms :
5
Square Footage :
4,091 Sqft
Year Built :
1968
Lot Area :
0.80 Acre
Listing ID :
73489022
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Agent info
Robb Enterprises
  • Stephen E. Robb
  • View website
  • 617-212-0251
  • srobb@robbenterprises.com

Contact Agent

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.

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