Windsor Dr, Holliston, MA Property Records

Middlesex County and Holliston Town property records for 4 addresses on Windsor Dr, Holliston, MA · Last verified July 2026

Windsor Dr Highlights

Properties 36
Median Sale Price $239,900
Deeds and Mortgages on File 35
Median Price per Sqft $256
Owner Occupied 61%
Median Annual Tax Bill $3,327
Median Year Built 1970
Median Ownership Tenure 10 years

Properties on Windsor Dr

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17 Windsor Dr

4 units · Built 1969 · 864 sq ft

Last Sale Median Tax Bill Median Sale    
$235,000Mar 2021 $3,6872025 $210,0004 units    

30 Windsor Dr

4 bd · 1.5 ba · 2,319 sqft · built 1989 · 0.91 acres

Last Sale Tax Bill Prior Sale Owner Records
$595,000Sep 2021 $10,7112025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

49 Windsor Dr

30 units · Built 1970 · 654 sq ft

Last Sale Median Tax Bill Median Sale    
$293,000Jun 2025 $3,3072025 $239,90030 units    

50 Windsor Dr

3 bd · 2 ba · 1,058 sqft · built 1986 · 1.55 acres

Last Sale Tax Bill Prior Sale Owner Records
$202,500Aug 1997 $9,3042025 Amount on Record Jun 1994 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

Wildfire Risk on Windsor Dr

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

Wildfire RiskLow
this street's cells rank above 5% of the US · above 10% of Massachusetts
Wildfire LikelihoodLess than 1 in 10,000 per year
ExposureDirect
1 of 2 cells directly exposed · 1 adjoin burnable vegetation

Property Records in Nearby Streets