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Deb Rees
REALTOR®
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22 Winslow Drive, Orleans, MA 02653

$2,300,000
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Active
BEDS5 BATHS5 full SQUARE FEET4,091 MLS#73489022
STATUSActive PROPERTY TYPEResidential - Single Family

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.

22 Winslow Drive | MLS# 73489022

This single family home located at 22 Winslow Drive, Orleans, MA 02653 is currently listed for sale with an asking price of $2,300,000. This property was built in 1968 and has 5 bedrooms and 5 full baths with 4091 sq. ft. Search Orleans real estate on debrees.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Full, Interior Entry, Bulkhead
Cooling: Central Air, Heat Pump
Fireplaces: 3
Garage: 2
Heating: Forced Air, Heat Pump, Electric
Home Style: Cape
Lot Size: 0.80 Acres
Taxes: $9,487
Year Built: 1968

Feature Descriptions

Building Area Total: 4091
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Days on Site: 29
Fireplace Y/N: Yes
GarageY/N: Yes
HeatingY/N: 1
Lot Features: Sloped
Parcel Number: M:092.0 B:0006 L:0000.0,2365770
Parking Features: Detached
Parking Total: 8
Rooms Total: 11
Sewer: Private Sewer
Water: Public, Private
Waterfront Features: Waterfront, Pond,1/2 to 1 Mile To Beach

Listed By / Shown By

Listed By

Agency Name: Gibson Sotheby's International Realty
Agency Phone: 508-255-6000
Agent Name: Whitaker Group Cape Cod

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Estimated Payment

$ 6,580.22 per month $5,118.80 Principal & Interest $790.58 Property Tax $670.83 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/17/2026. The listing information on this page last changed on 04/17/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 04/17/2026 5:02:47 AM EST) or MLSPIN MLS (last updated Thu 04/16/2026 11:38:34 PM EST) or Prime MLS (last updated Thu 04/16/2026 11:33:24 PM EST) or MREIS (last updated Fri 04/17/2026 2:05:22 AM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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