139 High Street Winchester, MA ^$ 969,000

139 High Street

^$ 969,000

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139 High Street

Winchester, MA, 01890

^$ 969,000

Bedrooms3 Baths1.1 Sq 1,302

Monthly Estimate*

^$ 6,045

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Single Family Home for sale in Winchester, MA

for $969,000 with 3 bedrooms and 1 full bath, 1 half bath. This 1,302 square foot home was built in 1949 on a lot size of 0.51.

This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with contemporary finishes. The dining room with built-in China cabinet provides an inviting space to entertain. Enjoy morning coffee or evening relaxation on the unheated 3-season porch overlooking the yard, with seasonal views of the Boston skyline. The lower level features high ceilings with a heating and cooling unit already installed, offering great potential for 200+ sqft of future finished space. Additional highlights include a one-car garage under and a convenient layout with timeless appeal. Nestled beside conservation land, this home provides a peaceful, natural setting where you can enjoy watching birds and local wildlife right from the yard. Make this one yours for 2026!

Single Family Active

Price

^$ 969,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 11,344

Style

Cape

Lot Size

0.51

Year Built

1949

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73453920

List By

Katie Tully

Listing Agent

Better Homes And Gardens Real Estate - The Shanahan Group

Broker

Affordability Calculator

$6,991

Per Month

Monthly Principal & Interest: $6,045
Monthly Property Taxes: $945
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.375% 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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Nearby

Trends

Single family listings in Winchester, MA

Average List Price ^$1,953,789

Percent of Sale Price 102%

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.

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Pricing History

Date	Price	Price Change	Description
12/3/2025	$969,000	-3.00%	Price Down
11/12/2025	$999,000		Listed Price

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139 High Street, Winchester, MA, 01890 is a Single Family Home for sale at $969,000 with 1,302 sqft and a lot size of 0.51. 139 High Street has 3 bedrooms, 1.1 baths, and was built in 1949. 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 6.375% 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 12/17/2025.

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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139 High Street

Single Family Home for sale in Winchester, MA

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