High St Hill Rd, Windsor, MA Property Records

Berkshire County and Windsor Town property records for 33 addresses on High St Hill Rd, Windsor, MA · Last verified August 2026

High St Hill Rd Highlights

Properties 33
Median Sale Price $449,900
Deeds and Mortgages on File 35
Median Price per Sqft $259
Owner Occupied 85%
Median Annual Tax Bill $3,707
Median Year Built 1987
Median Ownership Tenure 22 years

Properties on High St Hill Rd

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

40 High St Hill Rd

2 bd · 2.5 ba · 1,877 sqft · built 1989 · 11.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$70,000Mar 2005 $4,5272025 Amount on Record May 2000 1 Name on Record AssessorUpdated Apr 2026

85 High St Hill Rd

3 bd · 1.5 ba · 1,344 sqft · built 1987 · 8.09 acres

Last Sale Tax Bill Prior Sale Owner Records
$180,000Aug 2012 $2,6742025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

105 High St Hill Rd

3 bd · 3.5 ba · 1,694 sqft · built 1988 · 6.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$460,000Dec 2023 $4,7442025 Amount on Record Oct 2012 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

110 High St Hill Rd

1 bd · 2 ba · 1,000 sqft · built 2006 · 8.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$31,500Oct 2002 $3,6632025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

130 High St Hill Rd

3 bd · 2.5 ba · 2,240 sqft · built 2004 · 5.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$460,000Dec 2024 $4,0252025 Amount on Record Jul 2004 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

135 High St Hill Rd

3 bd · 2 ba · 1,924 sqft · built 1990 · 5.66 acres

Last Sale Tax Bill Prior Sale Owner Records
$15,000Aug 2001 $3,0972025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

155 High St Hill Rd

3 bd · 2.5 ba · 2,572 sqft · built 2003 · 10 acres

Last Sale Tax Bill Prior Sale Owner Records
$685,000Oct 2025 $5,8822025 Amount on Record Jul 2020 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

162 High St Hill Rd

2 bd · 2 ba · 1,395 sqft · built 1989 · 5.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,400Sep 1985 $3,2312025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

186 High St Hill Rd

4 bd · 2.5 ba · 1,352 sqft · built 1988 · 4.89 acres

Last Sale Tax Bill Prior Sale Owner Records
$210,000Nov 2017 $3,0532025 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

215 High St Hill Rd

3 bd · 2 ba · 1,260 sqft · built 2006 · 4.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$42,900Jun 2006 $3,0742025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

235 High St Hill Rd

3 bd · 2.5 ba · 1,736 sqft · built 2001 · 3.61 acres

Last Sale Tax Bill Prior Sale Owner Records
$449,900Jan 2023 $5,0472025 Amount on Record Apr 2022 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

255 High St Hill Rd

4 bd · 3.5 ba · 3,744 sqft · built 1987 · 3.24 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,2632025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

275 High St Hill Rd

5 bd · 2 ba · 2,358 sqft · built 2017 · 2.86 acres

Last Sale Tax Bill Prior Sale Owner Records
$17,500Jul 2016 $4,2512025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

300 High St Hill Rd

3 bd · 2 ba · 1,536 sqft · built 1977 · 6.36 acres

Last Sale Tax Bill Prior Sale Owner Records
$60,000Jun 2022 $3,7072025 Amount on Record Oct 2014 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

309 High St Hill Rd

3 bd · 2.5 ba · 2,152 sqft · built 1987 · 4.48 acres

Last Sale Tax Bill Prior Sale Owner Records
$155,000Jun 2000 $4,1022025 2 Names on Record AssessorUpdated Apr 2026

345 High St Hill Rd

2 bd · 2 ba · 1,584 sqft · built 1975 · 12 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,7812025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

376 High St Hill Rd

2 bd · 3 ba · 2,636 sqft · built 1967 · 4.43 acres

Last Sale Tax Bill Prior Sale Owner Records
$32,000Jul 1974 $4,7652025 2 Names on Record AssessorUpdated Apr 2026

449 High St Hill Rd

3 bd · 1 ba · 2,066 sqft · built 1974 · 2.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$265,000Mar 2021 $3,2812025 Amount on Record Jun 2020 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

522 High St Hill Rd

3 bd · 1 ba · 1,479 sqft · built 1837 · 1.83 acres

Last Sale Tax Bill Prior Sale Owner Records
$13,000Apr 1977 $2,0482025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

661 High St Hill Rd

3 bd · 2.5 ba · 2,552 sqft · built 1850 · 26 acres

Last Sale Tax Bill Prior Sale Owner Records
$400,000Oct 2016 $5,4902025 Amount on Record Apr 2011 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

716 High St Hill Rd

3 bd · 1.5 ba · 1,000 sqft · built 1973 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$94,000Nov 1999 $2,2522025 Amount on Record Jan 1995 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

756 High St Hill Rd

2 bd · 3 ba · 1,276 sqft · built 1972 · 8.04 acres

Last Sale Tax Bill Prior Sale Owner Records
$85,000Sep 2001 $2,6832025 Amount on Record Apr 1999 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

772 High St Hill Rd

3 bd · 2 ba · 2,448 sqft · built 1973 · 3.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,200Aug 1972 $3,8412025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

801 High St Hill Rd

3 bd · 2.5 ba · 1,846 sqft · built 1987 · 3.07 acres

Last Sale Tax Bill Prior Sale Owner Records
$160,000Mar 2001 $3,5782025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

812 High St Hill Rd

4 bd · 2.5 ba · 2,955 sqft · built 1972 · 9.57 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,1862025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

829 High St Hill Rd

3 bd · 2 ba · 1,419 sqft · built 1987 · 3.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$18,000Dec 1986 $3,0312025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

832 High St Hill Rd

3 bd · 1 ba · 1,256 sqft · built 1972 · 2.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,2302025 1 Name on Record AssessorUpdated Apr 2026

915 High St Hill Rd

3 bd · 2 ba · 1,396 sqft · built 1987 · 4.91 acres

Last Sale Tax Bill Prior Sale Owner Records
$397,000Oct 2025 $4,8392025 Amount on Record Feb 2016 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

978 High St Hill Rd

3 bd · 2.5 ba · 1,700 sqft · built 1997 · 4.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$259,900Dec 2004 $3,5412025 Amount on Record Oct 2001 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

1005 High St Hill Rd

4 bd · 2.5 ba · 1,700 sqft · built 1988 · 9 acres

Last Sale Tax Bill Prior Sale Owner Records
$34,500Jan 1996 $3,6082025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

1016 High St Hill Rd

3 bd · 2.5 ba · 1,849 sqft · built 1976 · 10 acres

Last Sale Tax Bill Prior Sale Owner Records
$396,000Sep 2019 $4,7812025 Amount on Record Nov 1974 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

1060 High St Hill Rd

4 bd · 3.5 ba · 2,869 sqft · built 2005 · 50 acres

Last Sale Tax Bill Prior Sale Owner Records
$80,000Nov 2003 $6,3442025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026
Last Sale Tax Bill Prior Sale Owner Records
$5,000Nov 1969 $3,3952025 2 Names on Record AssessorUpdated Apr 2026

Wildfire Risk on High St Hill 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
16 of 17 cells directly exposed · 17 adjoin burnable vegetation

Property Records in Nearby Streets