Winchester Dr, Bedford, MA Property Records

Middlesex County and Bedford Town property records for 10 addresses on Winchester Dr, Bedford, MA · Last verified September 2026

Winchester Dr Highlights

Properties 10
Median Sale Price $720,000
Deeds and Mortgages on File 14
Median Price per Sqft $432
Owner Occupied 100%
Median Annual Tax Bill $128
Median Year Built 1966
Median Ownership Tenure 10 years

Properties on Winchester Dr

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

1 Winchester Dr

4 bd · 2.5 ba · 2,064 sqft · built 1966 · 0.694 acres

Last Sale Tax Bill Prior Sale Owner Records
$555,000Oct 2008 $982025 2 Owners on Record Owner Occupied AssessorUpdated Apr 2026

2 Winchester Dr

4 bd · 3.5 ba · 1,480 sqft · built 1966 · 0.688 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,065,000May 2022 $1332025 Amount on Record Jul 2013 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

4 Winchester Dr

6 bd · 4 ba · 3,102 sqft · built 1967 · 0.689 acres

Last Sale Tax Bill Prior Sale Owner Records
$644,500Dec 2012 $1332025 2 Owners on Record Owner Occupied AssessorUpdated Apr 2026

5 Winchester Dr

4 bd · 2.5 ba · 3,124 sqft · built 1965 · 0.717 acres

Last Sale Tax Bill Prior Sale Owner Records
$284,500Dec 1994 $1282025 Amount on Record Jan 1991 Owner on Record Owner Occupied AssessorUpdated Apr 2026

6 Winchester Dr

6 bd · 4.5 ba · 3,588 sqft · built 2016 · 0.691 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,165,000Jan 2017 $18,0402025 Amount on Record Oct 2015 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Sep 2026

7 Winchester Dr

4 bd · 2.5 ba · 1,982 sqft · built 1965 · 0.713 acres

Last Sale Tax Bill Prior Sale Owner Records
$299,000Sep 1989 $1002025 2 Owners on Record Owner Occupied AssessorUpdated Apr 2026

8 Winchester Dr

4 bd · 2.5 ba · 1,600 sqft · built 1966 · 0.692 acres

Last Sale Tax Bill Prior Sale Owner Records
$718,000Sep 2016 $1102025 —Nov 2014 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

9 Winchester Dr

4 bd · 2.5 ba · 2,028 sqft · built 1965 · 0.692 acres

Last Sale Tax Bill Prior Sale Owner Records
$565,500Aug 2012 $992025 2 Owners on Record Owner Occupied AssessorUpdated Apr 2026

10 Winchester Dr

3 bd · 3.5 ba · 1,434 sqft · built 1965 · 0.688 acres

Last Sale Tax Bill Prior Sale Owner Records
$745,000Aug 2017 $1052025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

11 Winchester Dr

3 bd · 2.5 ba · 1,666 sqft · built 1966 · 0.688 acres

Last Sale Tax Bill Prior Sale Owner Records
$720,000Apr 2020 $11,7512025 Amount on Record May 1966 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

Property Records in Nearby Streets