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Zack Leroy
REALTOR®
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40 Pickering St, Winchester, MA 01890

$1,249,900
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New to the Market Active Under Contract
BEDS4 BATHS2 full 1 partial SQUARE FEET2,454 MLS#73484617
STATUSActive Under Contract PROPERTY TYPEResidential - Single Family

Property Description

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!

40 Pickering St | MLS# 73484617

This single family home located at 40 Pickering St, Winchester, MA 01890 is currently listed for sale with an asking price of $1,249,900. This property was built in 1870 and has 4 bedrooms and 2 full and 1 partial baths with 2454 sq. ft. Search Winchester real estate on zackleroy.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Fireplaces: 1
Heating: Baseboard, Hot Water, Propane
Home Style: Colonial
Lot Size: 0.16 Acres
Taxes: $11,312
Year Built: 1870

Feature Descriptions

Building Area Total: 2454
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Days on Site: 5
Fireplace Y/N: Yes
HeatingY/N: 1
Lot Features: Corner Lot
Parcel Number: M:014 B:0180 L:0,898516
Parking Total: 2
Rooms Total: 8
Sewer: Public Sewer
Water: Public

Listed By / Shown By

Listed By

Agency Name: Keller Williams Realty Signature Properties
Agency Phone: 781-924-5766
Agent Name: Timothy Haynes

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Shown By

Agent Name: Zack Leroy
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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Estimated Payment

$ 4,088.96 per month $2,781.74 Principal & Interest $942.67 Property Tax $364.55 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information 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. Information on this site was last updated 03/15/2026. The listing information on this page last changed on 03/15/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sun 03/15/2026 9:18:40 AM EST) or MLSPIN MLS (last updated Sun 03/15/2026 9:14:52 AM EST) or Prime MLS (last updated Sun 03/15/2026 9:10:34 AM EST) or MREIS (last updated Sun 03/15/2026 9:16:37 AM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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