257 Cross Street Winchester, MA ^$ 1,050,000

257 Cross Street

^$ 1,050,000

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257 Cross Street

Winchester, MA, 01890

^$ 1,050,000

Bedrooms5 Baths2.1 Sq 2,801

Monthly Estimate*

^$ 6,630

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Single Family Home for sale in Winchester, MA

for $1,050,000 with 5 bedrooms and 2 full baths, 1 half bath. This 2,801 square foot home was built in 1960 on a lot size of 0.24.

Situated on a large,10k+ level corner lot with frontage on both Cross Street and Verplast Avenue! The upper level features a fireplaced living room w picture window, updated kitchen, three bedrooms, 1.5 baths, and a large sunroom overlooking the expansive backyard. The first level offers additional flexible living space with a kitchenette, living area, two bedrooms, laundry, and a full bath, providing great potential for an in-law setup, guest space, home offices, or extended living. The generous lot and existing footprint create an ideal opportunity to modernize the home, expand the living space, or explore future possibilities. Put your personal touch on this home and build some great equity! This property is full of potential and ready for its next chapter!

Single Family Active

Price

^$ 1,050,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 9,849

Style

Ranch

Lot Size

0.24

Year Built

1960

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73571418

List By

Kim Covino & Co. Team

Listing Agent

Compass

Broker

Affordability Calculator

$7,451

Per Month

Monthly Principal & Interest: $6,630
Monthly Property Taxes: $821
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.49% 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.

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Trends

Single family listings in Winchester, MA

Average List Price ^$2,074,755

Percent of Sale Price 98%

About Winchester, MA

22,228 Population

7% Since 2002

^$152,119 Median Income

45.68 Median Age

42% Households with Children

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Trends Information provided by ATTOM Data Solutions.

Neighborhood & Schools

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Pricing History

Date	Price	Price Change	Description
9/3/2026	$1,050,000		Listed Price

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257 Cross Street, Winchester, MA, 01890 is a Single Family Home for sale at $1,050,000 with 2,801 sqft and a lot size of 0.24. 257 Cross Street has 5 bedrooms, 2.1 baths, and was built in 1960. The property's zip code is 01890 which is in Winchester, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% 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 9/8/2026.

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.

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257 Cross Street

Single Family Home for sale in Winchester, MA

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