Overlooking a tranquil pond, 22 Winslow Drive offers a peaceful

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Home For Sale

22 Winslow Drive

Orleans, Massachusetts 02653

Barnstable County

Waterfront: Yes

Community: 

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$2,300,000 5 br, 5.0 bath 4091 sq. ft. 0.800 acres

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.

Interior:
  • Bedrooms: 5
  • Baths: 5.0
  • Sq Ft: 4091
  • Year Built: 1968
  • Utilities: 
  • Fireplaces: Has Fireplace
  • Stories: 2
  • Heat/AC: Forced Air
  • Garage: Driveway, Open
Exterior:
  • Lot Size: 0.800 acre
  • Lot Dimensions: 
  • Waterfront: Yes
  • View Types: Lake
  • Yard: 
  • Siding: Clapboard
  • Roof: Asphalt
  • Property Taxes: $9,487
  • MLS #: 22600770
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Contact Information:
Beach Home For Sale in Orleans, Massachusetts
Listing Agent: Whitaker Group Cape Cod, Gibson Sotheby's International Realty, 508-237-8038, 508-255-6000 Listing Site, Listing Status: Active
Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc.. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Ad Number: 7439357
Viewed 6 times.
Updated: Mar 20, 2026

This property is a Home located at 22 Winslow Drive, Orleans, Massachusetts 02653, and is currently For Sale at $2,300,000. This Home has 5 bedrooms, 5.0 baths, 4091 sq ft.