Hillside Dr, Sturbridge, MA Property Records

Worcester County and Sturbridge Town property records for 32 addresses on Hillside Dr, Sturbridge, MA · Last verified August 2026

Hillside Dr Highlights

Properties 32
Median Sale Price $180,000
Deeds and Mortgages on File 41
Median Price per Sqft $72
Owner Occupied 88%
Median Annual Tax Bill $6,957
Median Year Built 1970
Median Ownership Tenure 10 years

Properties on Hillside Dr

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

2 Hillside Dr

3 bd · 2 ba · 1,909 sqft · 0.769 acres

Last Sale Tax Bill Prior Sale Owner Records
$287,858May 2016 $7,3582025 Amount on Record May 2014 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

2A Hillside Dr

1 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,000Dec 2000 $112025 1 Name on Record AssessorUpdated Apr 2026

3 Hillside Dr

3 bd · 1.5 ba · 1,552 sqft · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$78,000May 1995 $6,8472025 Amount on Record Jan 1995 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

4 Hillside Dr

5 bd · 2 ba · 3,448 sqft · 0.78 acres

Last Sale Tax Bill Prior Sale Owner Records
$144,000May 1994 $8,0812025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

6 Hillside Dr

3 bd · 2.5 ba · 2,097 sqft · 0.719 acres

Last Sale Tax Bill Prior Sale Owner Records
$555,000Oct 2025 $8,0352025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

7 Hillside Dr

4 bd · 3 ba · 1,829 sqft · 0.953 acres

Last Sale Tax Bill Prior Sale Owner Records
$310,000Jul 2020 $6,4152025 Amount on Record Aug 2003 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

8 Hillside Dr

3 bd · 2.5 ba · 1,241 sqft · 0.75 acres

Last Sale Tax Bill Prior Sale Owner Records
$61,000Jun 2020 $7,4502025 Amount on Record Oct 1989 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

10 Hillside Dr

2 bd · 2 ba · 1,614 sqft · 0.845 acres

Last Sale Tax Bill Prior Sale Owner Records
$286,425Oct 2018 $5,6342025 Amount on Record Jan 1987 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

11 Hillside Dr

4 bd · 3 ba · 2,229 sqft · 1.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$375,500Jul 2020 $8,7392025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

12 Hillside Dr

3 bd · 1 ba · 1,192 sqft · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$97,000Oct 1997 $5,3412025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

13 Hillside Dr

3 bd · 2 ba · 1,606 sqft · 1.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$365,000Jul 2020 $7,3682025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

17 Hillside Dr

4 bd · 2.5 ba · 2,454 sqft · 1.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$145,000Mar 1997 $7,7722025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

18 Hillside Dr

2 bd · 1 ba · 1,185 sqft · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000Jul 2018 $5,8402025 Amount on Record May 2015 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

19 Hillside Dr

4 bd · 3.5 ba · 3,244 sqft · 0.96 acres

Last Sale Tax Bill Prior Sale Owner Records
$460,000Aug 2016 $9,4392025 Amount on Record Jul 2014 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

20 Hillside Dr

3 bd · 1.5 ba · 1,302 sqft · 1.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,8802025 1 Name on Record Assessor + 4 DocumentsUpdated Jul 2026

24 Hillside Dr

3 bd · 2 ba · 1,232 sqft · 1.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$228,000Oct 2016 $5,5452025 Amount on Record Aug 2010 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

25 Hillside Dr

3 bd · 3 ba · 1,444 sqft · 0.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Feb 2011 $6,5632025 Amount on Record Feb 2009 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

27 Hillside Dr

3 bd · 2.5 ba · 1,397 sqft · 0.95 acres

Last Sale Tax Bill Prior Sale Owner Records
$302,000Nov 2017 $6,5682025 Amount on Record Nov 2004 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

28 Hillside Dr

4 bd · 2 ba · 1,894 sqft · 1.35 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,000May 2024 $6,6062025 Amount on Record Nov 2009 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

31 Hillside Dr

3 bd · 2 ba · 1,792 sqft · 2.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$222,500Apr 2010 $6,8022025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

36 Hillside Dr

3 bd · 2.5 ba · 2,285 sqft · 1.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$219,700Jun 1987 $8,1612025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

38 Hillside Dr

3 bd · 2 ba · 1,858 sqft · 1.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$60,000May 2020 $12,2102025 —Jul 2016 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

39 Hillside Dr

4 bd · 2.5 ba · 2,272 sqft · 1.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$192,000Oct 1994 $7,9782025 Amount on Record Aug 1990 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

41 Hillside Dr

3 bd · 1.5 ba · 1,675 sqft · 1.06 acres

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2011 $6,5312025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

42 Hillside Dr

4 bd · 2.5 ba · 2,240 sqft · 1.13 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jul 2016 $6,6032025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

44 Hillside Dr

3 bd · 2.5 ba · 1,887 sqft · 1.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$689,000Jul 2023 $11,1672025 Amount on Record Nov 2016 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

46 Hillside Dr

5 bd · 3 ba · 2,944 sqft · 1.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$380,000Mar 2019 $8,1672025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

47 Hillside Dr

3 bd · 2.5 ba · 2,035 sqft · 1.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$295,250Apr 2016 $6,9572025 Amount on Record Jun 2007 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

48 Hillside Dr

4 bd · 3 ba · 2,534 sqft · 15.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$147,500Feb 2021 $12,5532025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

50 Hillside Dr

4 bd · 2.5 ba · 2,576 sqft · 27 acres

Last Sale Tax Bill Prior Sale Owner Records
$180,000Mar 2021 $5,6582025 1 Name on Record Assessor + 4 DocumentsUpdated Jul 2026

53 Hillside Dr

3 bd · 2.5 ba · 2,010 sqft · 31.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$145,000Mar 2021 $11,9092025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

63 Hillside Dr

64.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$100,000Jan 2012 $4602025 Amount on Record Jul 1997 1 Name on Record AssessorUpdated Apr 2026

Property Records in Nearby Streets