Pickering St, Winchester, MA Property Records

Middlesex County and Winchester Town property records for 7 addresses on Pickering St, Winchester, MA · Last verified July 2026

Pickering St Highlights

Properties 7
Median Sale Price $540,000
Deeds and Mortgages on File 14
Median Price per Sqft $332
Owner Occupied 86%
Median Annual Tax Bill $113
Median Year Built 1940
Median Ownership Tenure 7 years

Properties on Pickering St

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

32 Pickering St

3 bd · 2.5 ba · 1,623 sqft · 0.151 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$540,000Oct 2019 $712025 Amount on Record May 1994 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

34 Pickering St

4 bd · 1.5 ba · 1,623 sqft · 0.16 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$151,000Aug 1995 $692025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

36 Pickering St

4 bd · 4 ba · 3,433 sqft · 0.234 acres

Last Sale Tax Bill Prior Sale Owner Records
$492,000Mar 2011 $1442025 Amount on Record Jun 2010 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

38 Pickering St, #A

3 bd · 2.5 ba · 2,056 sqft · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,082,000May 2026 $9,6382025 Amount on Record Jun 2018 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

38 Pickering St, #B

3 bd · 2.5 ba · 2,188 sqft · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$490,000Nov 2012 $9,0122025 2 Names on Record AssessorUpdated Apr 2026

39 Pickering St

4 bd · 2 ba · 1,740 sqft · 0.124 acres

Last Sale Tax Bill Prior Sale Owner Records
$1022025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

40 Pickering St

4 bd · 2.5 ba · 2,454 sqft · 0.159 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,330,000Apr 2026 $1132025 Amount on Record Oct 2017 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

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