257 High Street Winchester, MA ^$ 3,299,000

257 High Street

^$ 3,299,000

Back to search

257 High Street

Winchester, MA, 01890 | Off Market

^$ 3,299,000

Bedrooms5 Baths5.2

Is this your home? Yes, I would like to know how much it is worth

This property is no longer available.

Find similar listings

257 High Street, Winchester, MA 01890 - Image 1

257 High Street, Winchester, MA 01890 - Image 2

257 High Street, Winchester, MA 01890 - Image 3

257 High Street, Winchester, MA 01890 - Image 4

257 High Street, Winchester, MA 01890 - Image 5

257 High Street, Winchester, MA 01890 - Image 6

257 High Street, Winchester, MA 01890 - Image 7

257 High Street, Winchester, MA 01890 - Image 8

257 High Street, Winchester, MA 01890 - Image 9

257 High Street, Winchester, MA 01890 - Image 10

257 High Street, Winchester, MA 01890 - Image 11

257 High Street, Winchester, MA 01890 - Image 12

257 High Street, Winchester, MA 01890 - Image 13

257 High Street, Winchester, MA 01890 - Image 14

257 High Street, Winchester, MA 01890 - Image 15

257 High Street, Winchester, MA 01890 - Image 16

257 High Street, Winchester, MA 01890 - Image 17

257 High Street, Winchester, MA 01890 - Image 18

257 High Street, Winchester, MA 01890 - Image 19

257 High Street, Winchester, MA 01890 - Image 20

257 High Street, Winchester, MA 01890 - Image 21

257 High Street, Winchester, MA 01890 - Image 22

257 High Street, Winchester, MA 01890 - Image 23

257 High Street, Winchester, MA 01890 - Image 24

257 High Street, Winchester, MA 01890 - Image 25

257 High Street, Winchester, MA 01890 - Image 26

257 High Street, Winchester, MA 01890 - Image 27

257 High Street, Winchester, MA 01890 - Image 28

257 High Street, Winchester, MA 01890 - Image 29

257 High Street, Winchester, MA 01890 - Image 30

257 High Street, Winchester, MA 01890 - Image 31

257 High Street, Winchester, MA 01890 - Image 32

257 High Street, Winchester, MA 01890 - Image 33

257 High Street, Winchester, MA 01890 - Image 34

257 High Street, Winchester, MA 01890 - Image 35

257 High Street, Winchester, MA 01890 - Image 36

257 High Street, Winchester, MA 01890 - Image 37

257 High Street, Winchester, MA 01890 - Image 38

257 High Street, Winchester, MA 01890 - Image 39

257 High Street, Winchester, MA 01890 - Image 40

257 High Street, Winchester, MA 01890 - Image 41

257 High Street, Winchester, MA 01890 - Image 42

More homes like this one

homes for you

More homes like this one

See all

Affordability Calculator

$22,542

Per Month

Monthly Principal & Interest: $20,313
Monthly Property Taxes: $2,230
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 Winchester, MA

Average List Price ^$2,021,400

Percent of Sale Price 39%

About Winchester, MA

22,228 Population

7% Since 2002

^$152,119 Median Income

45.68 Median Age

42% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

Neighborhood & Schools

MLS rules require that you sign in here to see more detail on this property.

*Information deemed reliable but not guaranteed.

Data is updated as of 1/16/2026.

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?

257 High Street

More homes like this one

Affordability Calculator

Neighborhood & Schools

Find more homes like this one