22 Winslow Drive

This property is no longer actively marketed. The last publicly available listing details are shown below; contact us for current availability.

About this home

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.

Listing last checked: October 17, 2026 at 4:51 PM EDTListing updated: September 9, 2026 at 12:49 PM EDT

Listed by Whitaker Group Cape Cod · Gibson Sotheby's International Realty · MLS #73489022

Request property information

Select a document to start a request. You can add others in the form. Availability varies.

Details at a glance

Interior5 property facts

Rooms: 11
Heating: Forced Air, Heat Pump, Electric
Cooling: Central Air, Heat Pump
Basement: Yes · Full, Interior Entry, Bulkhead
Fireplaces: 3

Building5 property facts

Style: Single Family Residence
Year built: 1968
Garage: 2
Parking: 8
Foundation: Concrete Perimeter

Land & utilities6 property facts

Lot size: 0.8 acres
Water: Public, Private
Sewer: Private Sewer
Waterfront: Y
Pool: Not reported
Zoning: R

Financial2 property facts

Annual taxes: $9,487
Assessment year: 2025

Location

More property insights

Automated value estimate $2,276,170

Estimated range $1,922,693–$2,629,646.

Automated estimates are not appraisals or guarantees of market value.

Request a professional market analysis

Photo-based condition insights

Overall presentation: above average

Explore more of Orleans

Continue your search in Orleans.

Need help making sense of this home?

About 22 Winslow Drive

Is this home available for a showing?

This home is no longer actively marketed. Ask our team about its current status or similar homes.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.

Bean Group · eXp Realty

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting 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, leasing or renting. 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, or as to the accuracy of any of the Images, set forth herein.

Call Text team