Hilltop Dr, North Windham, CT Property Records

Windham Town property records for 47 addresses on Hilltop Dr, North Windham, CT · Last verified August 2026

Hilltop Dr Highlights

Properties 47
Median Sale Price $249,500
Deeds and Mortgages on File 42
Median Price per Sqft $189
Owner Occupied 77%
Median Annual Tax Bill $4,720
Median Year Built 1999
Median Ownership Tenure 18 years

Properties on Hilltop Dr

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

4 Hilltop Dr

3 bd · 2 ba · 1,054 sqft · 0.258 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$170,000Oct 2005 $4,2992025 Amount on Record Dec 2001 1 Name on Record AssessorUpdated Jul 2026

6 Hilltop Dr

3 bd · 2 ba · 1,164 sqft · 0.264 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$136,900Jun 2002 $4,6872025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

8 Hilltop Dr

3 bd · 2 ba · 1,176 sqft · 0.27 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$111,000Jun 1999 $4,6872025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

10 Hilltop Dr

3 bd · 2 ba · 1,176 sqft · 0.276 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$167,900Sep 2009 $4,6862025 Amount on Record Aug 2008 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

12 Hilltop Dr

3 bd · 2.5 ba · 1,362 sqft · 0.282 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$146,900May 2018 $5,7822025 —Sep 2017 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

14 Hilltop Dr

3 bd · 2 ba · 1,078 sqft · Garage

Last Sale Tax Bill Prior Sale Owner Records
$160,000Oct 2019 $4,3602025 Amount on Record Jun 2011 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

15 Hilltop Dr

3 bd · 1.5 ba · 1,320 sqft · 0.276 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$250,000Sep 2022 $4,6052025 Amount on Record Dec 2008 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

16 Hilltop Dr

3 bd · 1 ba · 1,362 sqft · 0.247 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$118,500Oct 1998 $4,8902025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

17 Hilltop Dr

2 bd · 1 ba · 924 sqft · 0.326 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$171,000May 2007 $4,0202025 Amount on Record Dec 2001 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

18 Hilltop Dr

5 bd · 2.5 ba · 1,362 sqft · 0.286 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$132,400Nov 1998 $5,6072025 2 Names on Record AssessorUpdated Jul 2026

19 Hilltop Dr

3 bd · 3 ba · 1,176 sqft · 0.313 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$210,000May 2008 $5,9002025 Amount on Record Jun 2002 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

20 Hilltop Dr

2 bd · 2 ba · 1,164 sqft · Garage

Last Sale Tax Bill Prior Sale Owner Records
$145,000Jun 2019 $4,6052025 Amount on Record Jan 2019 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

21 Hilltop Dr

2 bd · 1.5 ba · 1,020 sqft · 0.263 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$140,000Aug 2004 $4,2022025 Amount on Record Jun 1997 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

22 Hilltop Dr

3 bd · 2 ba · 1,048 sqft · 0.252 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$130,800Feb 1998 $4,5042025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

23 Hilltop Dr

3 bd · 2 ba · 1,146 sqft · 0.261 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$136,550Apr 2001 $4,6502025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

24 Hilltop Dr

3 bd · 1 ba · 1,362 sqft · 0.252 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$175,000Jul 2008 $4,8902025 Amount on Record Aug 1999 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

25 Hilltop Dr

3 bd · 1.5 ba · 1,320 sqft · 0.261 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$196,000Apr 2010 $5,1542025 Amount on Record Feb 2002 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

26 Hilltop Dr

3 bd · 2 ba · 1,122 sqft · 0.252 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$206,000Jun 2007 $4,6382025 Amount on Record Jan 2007 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

27 Hilltop Dr

2 bd · 1.5 ba · 924 sqft · 0.261 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$147,000Jul 2018 $4,3382025 Amount on Record May 2013 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

28 Hilltop Dr

3 bd · 2 ba · 1,164 sqft · Garage

Last Sale Tax Bill Prior Sale Owner Records
$129,000Sep 2019 $4,6542025 —Sep 2018 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

29 Hilltop Dr

2 bd · 1 ba · 924 sqft · 0.261 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$172,000Jan 2008 $3,9232025 Amount on Record Aug 1999 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

31 Hilltop Dr

2 bd · 1.5 ba · 924 sqft · 0.263 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$92,600Nov 1998 $3,9242025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

32 Hilltop Dr

3 bd · 2.5 ba · 1,080 sqft · 0.276 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$178,000Mar 2021 $4,3922025 Amount on Record Jul 2004 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

33 Hilltop Dr

3 bd · 2 ba · 1,176 sqft · 0.33 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$145,900Jan 2004 $4,7202025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

34 Hilltop Dr

3 bd · 2.5 ba · 1,362 sqft · 0.311 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$293,000Aug 2025 $5,3722025 Amount on Record Aug 2002 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

35 Hilltop Dr

3 bd · 1.5 ba · 1,320 sqft · 0.38 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$228,000Feb 2021 $4,4572025 Amount on Record Jul 2006 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

36 Hilltop Dr

3 bd · 2 ba · 1,076 sqft · 0.295 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$105,315Mar 2015 $4,5452025 —Nov 2014 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

37 Hilltop Dr

3 bd · 2.5 ba · 1,176 sqft · Garage

Last Sale Tax Bill Prior Sale Owner Records
$225,000Sep 2022 $5,2802025 Amount on Record Sep 2019 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

38 Hilltop Dr

3 bd · 2 ba · 1,164 sqft · 0.272 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$188,108Oct 2015 $4,6302025 Amount on Record Jan 2008 1 Name on Record AssessorUpdated Jul 2026

39 Hilltop Dr

3 bd · 2 ba · 1,176 sqft · 0.402 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4,7202025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

40 Hilltop Dr

3 bd · 2 ba · 1,362 sqft · 0.26 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$129,000Nov 2000 $5,0222025 Amount on Record Dec 1999 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

41 Hilltop Dr

2 bd · 2 ba · 924 sqft · 0.338 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Jul 2010 $4,9372025 Amount on Record Jul 2006 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

42 Hilltop Dr

3 bd · 2.5 ba · 1,362 sqft · 0.251 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$152,900Sep 2001 $5,0802025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

43 Hilltop Dr

3 bd · 1.5 ba · 1,320 sqft · 0.331 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$249,500Sep 2022 $5,1882025 Amount on Record Mar 2022 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

44 Hilltop Dr

3 bd · 2.5 ba · 1,054 sqft · 0.213 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$180,000Oct 2005 $4,6472025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

45 Hilltop Dr

3 bd · 2 ba · 1,158 sqft · Garage

Last Sale Tax Bill Prior Sale Owner Records
$268,000May 2024 $4,8092025 Amount on Record Feb 2020 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

46 Hilltop Dr

3 bd · 2.5 ba · 1,362 sqft · 0.206 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$213,600Dec 2021 $5,1892025 Amount on Record May 2002 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

47 Hilltop Dr

3 bd · 2 ba · 1,376 sqft · 0.434 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$126,000Feb 2017 $5,1822025 Amount on Record Aug 2012 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

49 Hilltop Dr

2 bd · 1 ba · 924 sqft · 0.498 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$125,900Oct 2003 $3,9232025 Amount on Record Jan 2002 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

51 Hilltop Dr

4 bd · 2.5 ba · 1,320 sqft · 0.474 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$204,000Dec 2005 $5,3182025 Amount on Record May 2002 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

52 Hilltop Dr

6 bd · 6,800 sqft · 0.378 acres

Last Sale Tax Bill Prior Sale Owner Records
$15,7742025 1 Name on Record AssessorUpdated Jul 2026

53 Hilltop Dr

2 bd · 1 ba · 924 sqft · 0.33 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$115,000Jan 2001 $3,9232025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

54 Hilltop Dr

6 bd · 7,028 sqft · 0.53 acres

Last Sale Tax Bill Prior Sale Owner Records
$15,5822025 1 Name on Record AssessorUpdated Jul 2026

55 Hilltop Dr

3 bd · 1.5 ba · 1,320 sqft · 0.354 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$137,000Jul 2002 $4,7272025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

59 Hilltop Dr

6 bd · 7,092 sqft · 0.521 acres

Last Sale Tax Bill Prior Sale Owner Records
$15,5822025 1 Name on Record AssessorUpdated Jul 2026

61 Hilltop Dr

6 bd · 7,106 sqft · 0.444 acres

Last Sale Tax Bill Prior Sale Owner Records
$15,5822025 1 Name on Record AssessorUpdated Jul 2026

63 Hilltop Dr

6 bd · 7,336 sqft · 0.825 acres

Last Sale Tax Bill Prior Sale Owner Records
$16,4022025 1 Name on Record AssessorUpdated Jul 2026

Wildfire Risk on Hilltop 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 · 55th in Connecticut
Wildfire LikelihoodLow — about 1 in 10,000 per year
ExposureDirect
1 of 3 cells directly exposed · 2 adjoin burnable vegetation

Property Records in Nearby Streets