Jackson Dr, Holliston, MA Property Records

Middlesex County and Holliston Town property records for 34 addresses on Jackson Dr, Holliston, MA · Last verified August 2026

Jackson Dr Highlights

Properties 34
Median Sale Price $635,000
Deeds and Mortgages on File 77
Median Price per Sqft $247
Owner Occupied 91%
Median Annual Tax Bill $10,551
Median Year Built 2017
Median Ownership Tenure 8 years

Properties on Jackson Dr

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

1 Jackson Dr

2 bd · 3 ba · 2,389 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$589,325May 2017 $10,7062025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

5 Jackson Dr

2 bd · 1.5 ba · 2,547 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$615,555Jun 2017 $12,2812025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

6 Jackson Dr

2 bd · 2.5 ba · 2,436 sqft

Last Sale Tax Bill Prior Sale Owner Records
$1,270,000Jun 2026 $9,2922025 Amount on Record May 2017 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

8 Jackson Dr

2 bd · 3 ba · 2,473 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$503,715May 2017 $9,8212025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

9 Jackson Dr

2 bd · 3 ba · 2,547 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$638,790Feb 2017 $14,2692025 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

15 Jackson Dr

2 bd · 3.5 ba · 2,568 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$635,000May 2019 $12,4772025 Amount on Record Apr 2017 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

19 Jackson Dr

2 bd · 2.5 ba · 2,547 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$619,776Jun 2017 $12,6502025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

23 Jackson Dr

2 bd · 3 ba · 2,278 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$560,160Sep 2017 $10,1662025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

27 Jackson Dr

2 bd · 2.5 ba · 2,381 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$562,000Apr 2021 $9,3382025 Amount on Record Jul 2017 1 Name on Record Assessor + 5 DocumentsUpdated Aug 2026

29 Jackson Dr

2 bd · 2.5 ba · 2,457 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$499,885Jul 2017 $9,6002025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

33 Jackson Dr

2 bd · 2.5 ba · 2,464 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$517,700Sep 2017 $9,6062025 1 Name on Record Assessor + 3 DocumentsUpdated Jul 2026

35 Jackson Dr

2 bd · 2.5 ba · 2,473 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$533,880Aug 2017 $9,6902025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

39 Jackson Dr

2 bd · 3 ba · 2,246 sqft · 41.9 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$529,995Jul 2018 $9,2782025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

43 Jackson Dr

2 bd · 2.5 ba · 2,568 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$654,420Sep 2017 $12,9302025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

46 Jackson Dr

2 bd · 2.5 ba · 2,160 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$537,035Jan 2018 $9,5202025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

47 Jackson Dr

2 bd · 3 ba · 2,547 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$671,382Oct 2017 $12,7282025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

48 Jackson Dr

2 bd · 2.5 ba · 2,100 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$191,300Feb 2018 $4,5012025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

51 Jackson Dr

2 bd · 2.5 ba · 2,547 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$628,625Nov 2017 $12,4422025 2 Names on Record Assessor + 4 DocumentsUpdated Aug 2026

52 Jackson Dr

2 bd · 2.5 ba · 2,318 sqft · 41.9 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$530,000Jul 2020 $9,0072025 Amount on Record Dec 2017 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

54 Jackson Dr

2 bd · 2.5 ba · 2,040 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$191,300Jan 2018 $4,5012025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

55 Jackson Dr

2 bd · 3.5 ba · 2,547 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$616,525Nov 2017 $13,0932025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

58 Jackson Dr

2 bd · 2.5 ba · 2,457 sqft · 41.9 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$493,000Oct 2017 $9,6752025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

59 Jackson Dr

2 bd · 2.5 ba · 2,547 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$729,000Jul 2021 $12,6302025 Amount on Record Oct 2018 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

60 Jackson Dr

2 bd · 2.5 ba · 2,457 sqft · 41.9 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$515,215Oct 2017 $9,6382025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

63 Jackson Dr

2 bd · 2.5 ba · 2,409 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$511,450Dec 2017 $9,6762025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

64 Jackson Dr

2 bd · 3 ba · 2,269 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$583,745Feb 2018 $10,2772025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

65 Jackson Dr

2 bd · 2.5 ba · 2,647 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$521,045Dec 2017 $10,5512025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

69 Jackson Dr

2 bd · 2.5 ba · 2,547 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$625,000Jul 2018 $12,5352025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

70 Jackson Dr

2 bd · 2.5 ba · 2,547 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$580,000Feb 2019 $14,2002025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

73 Jackson Dr

2 bd · 3.5 ba · 2,568 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$761,710Mar 2018 $13,4752025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

74 Jackson Dr

2 bd · 3 ba · 2,269 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$539,000Jul 2019 $10,3562025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

78 Jackson Dr

2 bd · 2.5 ba · 2,547 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$879,900Jan 2024 $12,2252025 Amount on Record Feb 2019 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

81 Jackson Dr

2 bd · 2.5 ba · 2,604 sqft · 41.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$678,190Jul 2018 $12,5292025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

82 Jackson Dr

2 bd · 3.5 ba · 2,786 sqft · 41.9 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$592,500Sep 2020 $11,5352025 Amount on Record Oct 2018 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

Wildfire Risk on Jackson Dr

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

Wildfire RiskLow
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
ExposureDirect
1 of 1 cells directly exposed · 1 adjoin burnable vegetation

Property Records in Nearby Streets