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22 Winslow Drive, Orleans MA 02653

$2,150,000

Estimated $14,038/month Calculator

Single Family

5 Bedrooms

Baths

4091

Total Parking: 10 (2 Garage)

34,848 (0.80)

Built in 1968

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 home has been viewed 5 times

Last Checked: June 18th, 2026 at 5:03am (Source: MLS PIN #73489022)

Garage Parking

Air Conditioning

Waterview

Waterfront

Lead Paint Free

General Information for 22 Winslow Drive, Orleans MA 02653

Listing ID73489022

Property TypeSingle Family / Detached

Price$2,150,000 ($525.54/SqFt)

StyleColonial

CityOrleans

CountyBarnstable

Neighborhood(s)

Garage Parking2

ZoningR

Year Built1968

Year Built SourcePublic Records

Year Built DetailsActual

Interior Features for 22 Winslow Drive, Orleans MA 02653

Approximate Living Area Total4091

Living Area Includes BasementNo

Rooms11

Bedrooms5

Primary En Suite BathroomYes

BasementFull

Cooling1, Split

Fireplaces

Appliances

Flooring

Electric

Exterior Features for 22 Winslow Drive, Orleans MA 02653

Approximate Lot Size (Acres)0.8

Approximate Lot Size (Square Feet)34848

Total Parking10 (2 Garage)

Garage Parking2

WaterPublic,private

SewerPrivate Sewer

Lot FeaturesGentle Sloping

Parking Features1

Exterior Features

Foundation Materials

Construction Materials

Road Frontage Type

Patio & Porch

Roof Material

Utility Connections

Water ViewsYes

Water Views FeaturesBay

Waterfront1

Waterfront FeaturesRiver

Pool Features

Horse Permitted0

Horse AmenitiesRiver

Disclosures for 22 Winslow Drive, Orleans MA 02653

Lead PaintNone

UFFI

Living Area Includes BasementNo

Living Area Disclosure

Building Area SourcePublic Records

Special Listing Conditions

ExclusionsSome Of The Sellers' Personal Items Are Not Included In The Sale.

Title 5A

Compensation Based On

Financial Information for 22 Winslow Drive, Orleans MA 02653

Association Fee

Association Fee Frequency

Association Fee Includes

Real Estate Tax9487

Tax Year2025

Assessed Value$1,520,300

Location Information for 22 Winslow Drive, Orleans MA 02653

Neighborhood(s)

Area Amenities

Contact Information for 22 Winslow Drive, Orleans MA 02653

Agent

Name: Whitaker Group Cape Cod

Office

Name: Gibson Sotheby's International Realty

Phone: 508-255-6000

Payment Calculator

, Interest

Property Taxes 790.58

Principal & Interest 13247.62

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

Gibson Sotheby's International Realty

Whitaker Group Cape Cod

Agent Phone

Office Phone

(508) 255-6000

Text Agent Call Agent Call Office

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EXIT

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