40 Pickering St Winchester, MA ^$ 1,249,900

40 Pickering St

^$ 1,249,900

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40 Pickering St

Winchester, MA, 01890

^$ 1,249,900

Bedrooms4 Baths2.1 Sq 2,454

Monthly Estimate*

^$ 7,696

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Single Family Home for sale in Winchester, MA

for $1,249,900 with 4 bedrooms and 2 full baths, 1 half bath. This 2,454 square foot home was built in 1870 on a lot size of 0.16.

This charming home retains period details while delivering flexible modern living. Through the glass-enclosed front porch, the first floor offers an entry stair hall, formal living room, a bedroom or home office with full bath and separate entrance, kid's homework room/drop zone, and - the star of the show - a sun-drenched open plan kitchen/family room with fireplace, massive island, and plenty of space for entertaining. Upstairs, there are three more bedrooms, a full bath and a half-bath, plus laundry and a sitting/play room. However you decide to use the 2400+sf, there's plenty of it. The roof, siding, water line and many windows were new when the sellers bought in 2017. Since then, they have installed new wiring, plumbing, heating and air conditioning. They re-did the kitchen and bathrooms. The floors are refinished, paint refreshed, and insulation upgraded. Outside, the sunny corner lot is partially fenced. Come take a look!

Single Family Active

Price

^$ 1,249,900

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 11,312

Style

Colonial

Lot Size

0.16

Year Built

1870

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73484617

List By

Timothy Haynes

Listing Agent

Keller Williams Realty Signature Properties

Broker

Affordability Calculator

$8,639

Per Month

Monthly Principal & Interest: $7,696
Monthly Property Taxes: $943
Monthly Home Insurance: --

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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.

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Trends

Single family listings in Winchester, MA

Average List Price ^$2,567,905

Percent of Sale Price 105%

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
3/10/2026	$1,249,900		Listed Price

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40 Pickering St, Winchester, MA, 01890 is a Single Family Home for sale at $1,249,900 with 2,454 sqft and a lot size of 0.16. 40 Pickering St has 4 bedrooms, 2.1 baths, and was built in 1870. 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 6.25% 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 3/11/2026.

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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40 Pickering St

Single Family Home for sale in Winchester, MA

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