Gregory Rd, Holliston, MA Property Records

Middlesex County and Holliston Town property records for 21 addresses on Gregory Rd, Holliston, MA · Last verified August 2026

Gregory Rd Highlights

Properties 21
Median Sale Price $550,000
Deeds and Mortgages on File 28
Median Price per Sqft $456
Owner Occupied 95%
Median Annual Tax Bill $8,818
Median Year Built 1964
Median Ownership Tenure 11 years

Properties on Gregory Rd

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

9 Gregory Rd

3 bd · 1.5 ba · 1,086 sqft · 0.439 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$420,000Aug 2024 $7,1162025 1 Name on Record AssessorUpdated Jul 2026

12 Gregory Rd

3 bd · 2 ba · 1,226 sqft · 0.45 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Apr 2012 $7,9302025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

21 Gregory Rd

4 bd · 2.5 ba · 2,944 sqft · 0.46 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$220,000Nov 2000 $13,0372025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

28 Gregory Rd

3 bd · 1.5 ba · 1,208 sqft · 0.41 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$340,000May 2016 $7,8492025 Amount on Record Oct 1989 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

29 Gregory Rd

3 bd · 1.5 ba · 1,416 sqft · 0.45 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Nov 2006 $8,9122025 Amount on Record Jul 1998 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

36 Gregory Rd

3 bd · 1 ba · 998 sqft · 0.41 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$550,000Oct 2023 $7,4472025 Amount on Record Mar 2019 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

37 Gregory Rd

4 bd · 1.5 ba · 1,950 sqft · 0.45 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$359,000May 2003 $9,6982025 Amount on Record Aug 1998 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

44 Gregory Rd

3 bd · 1.5 ba · 1,225 sqft · 0.41 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$530,000Oct 2022 $8,5192025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

45 Gregory Rd

4 bd · 2.5 ba · 2,274 sqft · 0.439 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$213,000May 1997 $9,5782025 Amount on Record Apr 1993 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

52 Gregory Rd

3 bd · 1.5 ba · 1,226 sqft · 0.5 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$560,000Sep 2021 $9,3912025 Amount on Record Dec 1991 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

53 Gregory Rd

3 bd · 2.5 ba · 1,415 sqft · 0.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$421,000Aug 2018 $9,8322025 Amount on Record Jun 1995 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

60 Gregory Rd

3 bd · 1.5 ba · 1,410 sqft · 0.41 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$41,500Apr 1976 $8,6642025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

61 Gregory Rd

3 bd · 2 ba · 1,651 sqft · 0.46 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$175,000Apr 1994 $8,8182025 —Apr 1987 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

68 Gregory Rd

2 bd · 2 ba · 1,226 sqft · 0.41 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$565,000Dec 2022 $8,6712025 Amount on Record Sep 1989 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

76 Gregory Rd

4 bd · 2.5 ba · 1,364 sqft · 0.51 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$650,000Jun 2022 $9,6782025 Amount on Record Jun 2016 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

79 Gregory Rd

3 bd · 1.5 ba · 1,225 sqft · 0.53 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
—Sep 2015 $8,9482025 Amount on Record Jul 1974 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

84 Gregory Rd

3 bd · 2 ba · 1,226 sqft · 0.43 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$157,400Apr 1986 $8,1002025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

92 Gregory Rd

4 bd · 1.5 ba · 1,740 sqft · 0.469 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2015 $9,0482025 Amount on Record Jun 1983 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

95 Gregory Rd

4 bd · 2 ba · 1,225 sqft · 0.46 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$295,000Dec 2001 $7,9522025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

100 Gregory Rd

3 bd · 2.5 ba · 1,226 sqft · 0.53 acres

Last Sale Tax Bill Prior Sale Owner Records
—May 2017 $9,1612025 Amount on Record Sep 2015 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

108 Gregory Rd

3 bd · 2.5 ba · 1,436 sqft · 0.46 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$375,000Apr 2019 $8,7862025 —Jun 2013 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

Wildfire Risk on Gregory Rd

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

Wildfire Risk to HomesLow
this street's cells rank at the 20th percentile of exposed land nationally · 58th in Massachusetts
Wildfire LikelihoodLow — about 1 in 10,000 per year
ExposureIndirect
0 of 2 cells directly exposed · 2 adjoin burnable vegetation

Property Records in Nearby Streets