Cheshire Rd, Windsor, MA Property Records

Berkshire County and Windsor Town property records for 16 addresses on Cheshire Rd, Windsor, MA · Last verified August 2026

Cheshire Rd Highlights

Properties 16
Median Sale Price $130,000
Deeds and Mortgages on File 9
Median Price per Sqft $127
Owner Occupied 50%
Median Annual Tax Bill $2,638
Median Year Built 1980
Median Ownership Tenure 16 years

Properties on Cheshire Rd

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

9 Cheshire Rd

3 bd · 2.5 ba · 2,208 sqft · built 1989 · 21 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,5482025 1 Name on Record AssessorUpdated Apr 2026

169 Cheshire Rd

1 bd · 1 ba · 576 sqft · built 1985 · 5.82 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,4712025 2 Names on Record AssessorUpdated Apr 2026

201 Cheshire Rd

2 bd · 1 ba · 1,216 sqft · built 1987 · 4.36 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,900Oct 1983 $1,8542025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

237 Cheshire Rd

4 bd · 2 ba · 2,544 sqft · built 1994 · 4.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$171,000Jun 1999 $4,4432025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

420 Cheshire Rd

1 bd · 1.5 ba · 1,236 sqft · built 1980 · 3.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$130,000Sep 2018 $2,4612025 —Jun 2013 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

501 Cheshire Rd

2 bd · 1 ba · 1,116 sqft · built 1940 · 4 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,8412025 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

541 Cheshire Rd

1 bd · 313 sqft · built 1973 · 41 acres

Last Sale Tax Bill Prior Sale Owner Records
$40,000Jun 2001 $6932025 1 Name on Record AssessorUpdated Apr 2026

884 Cheshire Rd

2 bd · 2 ba · 2,042 sqft · built 1970 · 41 acres

Last Sale Tax Bill Prior Sale Owner Records
$485,500Jan 2023 $4,5262025 —May 2018 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

935 Cheshire Rd

1 bd · 2 ba · 680 sqft · built 1950 · 234 acres

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2016 $2,6382025 1 Name on Record AssessorUpdated Apr 2026

948 Cheshire Rd

3 bd · 1 ba · 1,392 sqft · built 1986 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,8252025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

952 Cheshire Rd

3 bd · 4.5 ba · 1,716 sqft · built 1993 · 1.93 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,3412025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

980 Cheshire Rd

3 bd · 2 ba · 2,010 sqft · built 2013 · 9.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$84,000Aug 2010 $4,5162025 Amount on Record Mar 2004 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

1061 Cheshire Rd

3 bd · 1 ba · 1,315 sqft · built 1940 · 0.75 acres

Last Sale Tax Bill Prior Sale Owner Records
$20,000Sep 2015 $2842025 Amount on Record Feb 2005 1 Name on Record AssessorUpdated Apr 2026

1139 Cheshire Rd

1 bd · 1 ba · 600 sqft · built 1938 · 4.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$105,000Jan 2002 $8862025 1 Name on Record AssessorUpdated Apr 2026

1153 Cheshire Rd

2 bd · 1 ba · 1,283 sqft · built 1930 · 1.66 acres

Last Sale Tax Bill Prior Sale Owner Records
$170,000Jun 2021 $2,4952025 Amount on Record Oct 1993 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

1239 Cheshire Rd

2,242 sqft · 2.45 acres

Last Sale Tax Bill Prior Sale Owner Records
$18,000Sep 1994 $3362025 1 Name on Record AssessorUpdated Apr 2026

Wildfire Risk on Cheshire Rd

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskLow
this street's cells rank above 20% of the US · above 58% of Massachusetts
Wildfire LikelihoodAbout 1 in 10,000 per year
ExposureDirect
13 of 13 cells directly exposed · 13 adjoin burnable vegetation