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

22 Winslow Drive

^$ 2,300,000

Back to search

Recently Listed

22 Winslow Drive

Orleans, MA, 02653

^$ 2,300,000

Bedrooms5 Baths5.0 Sq 4,091

Monthly Estimate*

^$ 14,161

22 Winslow Drive, Orleans, MA 02653 - Image 1

22 Winslow Drive, Orleans, MA 02653 - Image 2

22 Winslow Drive, Orleans, MA 02653 - Image 3

22 Winslow Drive, Orleans, MA 02653 - Image 4

22 Winslow Drive, Orleans, MA 02653 - Image 5

22 Winslow Drive, Orleans, MA 02653 - Image 6

22 Winslow Drive, Orleans, MA 02653 - Image 7

22 Winslow Drive, Orleans, MA 02653 - Image 8

22 Winslow Drive, Orleans, MA 02653 - Image 9

22 Winslow Drive, Orleans, MA 02653 - Image 10

22 Winslow Drive, Orleans, MA 02653 - Image 11

22 Winslow Drive, Orleans, MA 02653 - Image 12

22 Winslow Drive, Orleans, MA 02653 - Image 13

22 Winslow Drive, Orleans, MA 02653 - Image 14

22 Winslow Drive, Orleans, MA 02653 - Image 15

22 Winslow Drive, Orleans, MA 02653 - Image 16

22 Winslow Drive, Orleans, MA 02653 - Image 17

22 Winslow Drive, Orleans, MA 02653 - Image 18

22 Winslow Drive, Orleans, MA 02653 - Image 19

22 Winslow Drive, Orleans, MA 02653 - Image 20

22 Winslow Drive, Orleans, MA 02653 - Image 21

22 Winslow Drive, Orleans, MA 02653 - Image 22

22 Winslow Drive, Orleans, MA 02653 - Image 23

22 Winslow Drive, Orleans, MA 02653 - Image 24

22 Winslow Drive, Orleans, MA 02653 - Image 25

22 Winslow Drive, Orleans, MA 02653 - Image 26

22 Winslow Drive, Orleans, MA 02653 - Image 27

22 Winslow Drive, Orleans, MA 02653 - Image 28

22 Winslow Drive, Orleans, MA 02653 - Image 29

22 Winslow Drive, Orleans, MA 02653 - Image 30

22 Winslow Drive, Orleans, MA 02653 - Image 31

22 Winslow Drive, Orleans, MA 02653 - Image 32

22 Winslow Drive, Orleans, MA 02653 - Image 33

22 Winslow Drive, Orleans, MA 02653 - Image 34

22 Winslow Drive, Orleans, MA 02653 - Image 35

Single Family Home for sale in Orleans, MA

for $2,300,000 with 5 bedrooms and 5 full baths. This 4,091 square foot home was built in 1968 on a lot size of 0.8.

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.

Single Family Active

Price

^$ 2,300,000

Bedrooms

Full Bath

Property Type

Single Family

Taxes

^$ 9,487

Style

Cape

Lot Size

0.8

Year Built

1968

Town/City

Orleans

County/Region

Barnstable

MLS | Web ID

73489022

List By

Whitaker Group Cape Cod

Listing Agent

Gibson Sotheby's International Realty

Broker

Affordability Calculator

$14,952

Per Month

Monthly Principal & Interest: $14,161
Monthly Property Taxes: $791
Monthly Home Insurance: --

Set your offer price

Down Payment

Loan Term

Interest Rate

Yearly Property Taxes

Yearly Home Insurance

Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

THE TIME TO SELL IS NOW! What's my home worth?

Nearby

Trends

Single family listings in Orleans, MA

Average List Price ^$2,072,026

Percent of Sale Price 10%

About Orleans, MA

5,780 Population

-8% Since 2002

^$64,589 Median Income

61.83 Median Age

10% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

Neighborhood & Schools

MLS Property Information Network, Inc rules require that you sign in here to see more detail on this property.

Pricing History

Date	Price	Price Change	Description
3/19/2026	$2,300,000		Listed Price

Map

More homes like this one

homes for you

See all

22 Winslow Drive, Orleans, MA, 02653 is a Single Family Home for sale at $2,300,000 with 4,091 sqft and a lot size of 0.8. 22 Winslow Drive has 5 bedrooms, 5.0 baths, and was built in 1968. The property's zip code is 02653 which is in Orleans, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 3/24/2026.

The real estate information and related content displayed on this site 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.

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 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 or leasing 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 or leasing. 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.

*Full Name

*Email

*Phone

I am interested in financing options

Get more info

By submitting the form, you agree that Weichert^® may contact you via phone or text about your inquiry, which may involve the use of automated means. You are not required to consent as a condition of purchasing any property, goods or services. For any other information please read our privacy policy.

Get more info

Looking for an Associate?

Already Working with an Associate?

22 Winslow Drive

Single Family Home for sale in Orleans, MA

Affordability Calculator

Neighborhood & Schools

Map

More homes like this one

Get more info about this home