40 Pickering St
Winchester, MA, 01890
$1,249,900
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!
Current real estate data for Single Family in Winchester as of Mar 14, 2026
45
Single Family Listed
59
Avg DOM
544
Avg $ / SqFt
$2,204,007
Avg List Price
Property Details
Price:
$1,249,900
MLS #:
73484617
Status:
Active Under Contract
Beds:
4
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Mar 10, 2026
Finished Sq Ft:
2,454
Total Sq Ft:
2,454
Lot Size:
6,965 sqft / 0.16 acres (approx)
Year Built:
1870
Schools
Interior
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
1
Heating
Baseboard, Hot Water, Propane
Exterior
Architectural Style
Colonial
Parking Spots
2
Financial
Tax Year
2025
Taxes
$11,312
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Community
- Address40 Pickering St Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Close to Wright Locke Farm
- Cox Road / High St Extension neighborhood
- East SIde near town forest!!
- Everett/ Stratford
- Flats location
- FLATS location Across from Wedgemere/Oxford
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Ledgewood Estates
- Middlesex
- Myopia Hill/ Winchester Country Club Area
- Near VO school
- old village/ West side
- The Flats
- Top neighborhood near town center
- West side
Property Summary
- 40 Pickering St Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,249,900 and features 4 beds, 3 baths, and has approximately 2,454 square feet of living space, and was originally constructed in 1870. The current price per square foot is $509. The average price per square foot for Single Family listings in Winchester is $544. The average listing price for Single Family in Winchester is $2,204,007. To schedule a showing of MLS#73484617 at 40 Pickering St in Winchester, MA, contact your Boardwalk Real Estate Corp. agent at 781-944-7820.
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CRP: Certified Relocation Professional CRS: Certified Residential Specialist GRI: Graduate of Realtors Institute CBR: Certified Buyers Representative BSBA: Bachelor of Science in Business Administration. Babson College 1979 MBA: Master of Business Administration. Babson College 2002 James M. Joly is President and Principal-Owner of Boardwalk Real Estate Corp.,…
More About JamesCourtesy of Keller Williams Realty Signature Properties. The property listing data and information 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 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 set forth herein.
40 Pickering St
Winchester, MA












































