22 Winslow Drive
Orleans, MA · $2,300,000
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22 Winslow Drive

Orleans, MA 02653
$2,300,000
24 days on market · Listed Mar 19, 2026
Data refreshed Apr 9, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
5
Baths
5
Sq Ft
4,091
Acres
0.8
Year Built
1968
$ / Sq Ft
$562
Days on Market
24

Investment Snapshot

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Location & Nearby

Map of 22 Winslow Drive, Orleans MA with nearby beaches and points of interest
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About this property

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.

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Listed by Whitaker Group Cape Cod, Gibson Sotheby's International Realty