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Properties

  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
  • 40 Pickering St, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 8 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Pickering St,73484617
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!

Features
Heating System:
Propane, Baseboard, Hot Water
Cooling System:
Central Air
Sewer:
Public Sewer
Style:
Colonial
Water:
Public
Disclosure:
exempt. Yard- grass is Syn Lawn synthetic 2 exterior photos virtually staged. See all attachments, Seller prefers to rent home furnished; ask listing agent for details. Tenant is responsible for all utilities.
Garage Parking
Lead Paint:
Yes
Additional Information
Parking Spaces:
2
Tax Year:
2025
Status:
Active
Price Per Sqft:
$509
Zoning:
RG
Orig Price:
$1,249,900
Fireplaces:
1
Waterfront:
No
MlsStatus:
New
Address Map
City:
Winchester
State:
MA
County:
Middlesex
Postal Code:
01890
Longitude:
W72° 51' 9''
Latitude:
N42° 27' 52.7''
  • Google Map

Residential

40 Pickering St, Winchester, Massachusetts

4 Bedrooms
2.5 Total Bathrooms
2,454 Sqft
$1,249,900
Listing ID #73484617
Basic Details
Property Type :
Residential
Listing Type :
For Sale
Price :
$1,249,900
Bedrooms :
4
Rooms :
8
Total Bathrooms :
2.5
Full Bathrooms :
2
Half Bathrooms :
1
Square Footage :
2,454 Sqft
Year Built :
1870
Lot Area :
0.16 Acre
Listing ID :
73484617
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Agent info
Robb Enterprises
  • Stephen E. Robb
  • View website
  • 617-212-0251
  • srobb@robbenterprises.com

Contact Agent

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.

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