Chestnut Dr, Windsor, CT Property Records

Windsor Town property records for 28 addresses on Chestnut Dr, Windsor, CT · Last verified August 2026

Chestnut Dr Highlights

Properties 28
Median Sale Price $255,000
Deeds and Mortgages on File 25
Median Price per Sqft $175
Owner Occupied 89%
Median Annual Tax Bill $5,383
Median Year Built 1955
Median Ownership Tenure 10 years

Properties on Chestnut Dr

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

3 Chestnut Dr

3 bd · 2 ba · 1,424 sqft · 0.519 acres

Last Sale Tax Bill Prior Sale Owner Records
$129,900Jul 1987 $5,5062024 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

4 Chestnut Dr

3 bd · 1 ba · 1,213 sqft · 0.569 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,000Sep 2018 $5,1762024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

7 Chestnut Dr

3 bd · 1 ba · 1,467 sqft · 0.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,6422024 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

11 Chestnut Dr

3 bd · 2 ba · 1,259 sqft · 0.53 acres

Last Sale Tax Bill Prior Sale Owner Records
$130,000Jan 2019 $5,1122024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

12 Chestnut Dr

2 bd · 1 ba · 1,152 sqft · 0.55 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,8432024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

15 Chestnut Dr

2 bd · 2 ba · 1,412 sqft · 0.53 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,2772024 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

16 Chestnut Dr

3 bd · 1 ba · 1,433 sqft · 0.55 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,4892024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

22 Chestnut Dr

3 bd · 1 ba · 1,225 sqft · 0.489 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,9772024 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

26 Chestnut Dr

2 bd · 1 ba · 800 sqft · 0.519 acres

Last Sale Tax Bill Prior Sale Owner Records
$145,900Aug 2016 $3,9952024 Amount on Record Nov 2010 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

29 Chestnut Dr

3 bd · 1 ba · 1,144 sqft · 0.55 acres

Last Sale Tax Bill Prior Sale Owner Records
$100,000Nov 1996 $4,6602024 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

30 Chestnut Dr

3 bd · 1.5 ba · 1,204 sqft · 0.53 acres

Last Sale Tax Bill Prior Sale Owner Records
$299,900May 2025 $4,7922024 Amount on Record Nov 2006 2 Names on Record Assessor + 3 DocumentsUpdated Jul 2026

33 Chestnut Dr

3 bd · 2.5 ba · 1,340 sqft · 0.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$176,900Mar 1989 $6,2532024 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

34 Chestnut Dr

3 bd · 2.5 ba · 1,384 sqft · 0.519 acres

Last Sale Tax Bill Prior Sale Owner Records
$320,500May 2024 $5,5402024 Amount on Record Oct 2022 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

37 Chestnut Dr

2 bd · 2.5 ba · 1,277 sqft · 0.55 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,3832024 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

38 Chestnut Dr

3 bd · 2 ba · 1,540 sqft · 0.519 acres

Last Sale Tax Bill Prior Sale Owner Records
$227,000Jun 2020 $5,6922024 Amount on Record Nov 2017 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

41 Chestnut Dr

2 bd · 2.5 ba · 1,452 sqft · 0.55 acres

Last Sale Tax Bill Prior Sale Owner Records
$255,000Feb 2026 $6,1902024 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

42 Chestnut Dr

2 bd · 2 ba · 1,455 sqft · 0.519 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,000Aug 2009 $5,7872024 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

45 Chestnut Dr

3 bd · 1.5 ba · 1,125 sqft · 0.66 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$265,500Jun 2023 $5,2182024 Amount on Record Jun 2022 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

46 Chestnut Dr

2 bd · 1.5 ba · 1,186 sqft · 0.489 acres

Last Sale Tax Bill Prior Sale Owner Records
$100,000Oct 1994 $5,6282024 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

51 Chestnut Dr

3 bd · 1.5 ba · 1,479 sqft · 0.739 acres

Last Sale Tax Bill Prior Sale Owner Records
$239,900Mar 2006 $5,1362024 Amount on Record Sep 2002 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

52 Chestnut Dr

3 bd · 2 ba · 1,468 sqft · 0.56 acres

Last Sale Tax Bill Prior Sale Owner Records
$210,000May 2016 $5,5962024 Amount on Record Apr 2015 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

55 Chestnut Dr

3 bd · 2 ba · 1,570 sqft · 0.61 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,2272024 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

56 Chestnut Dr

3 bd · 1 ba · 1,265 sqft · 0.56 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,1322024 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

59 Chestnut Dr

3 bd · 2.5 ba · 2,124 sqft · 0.61 acres

Last Sale Tax Bill Prior Sale Owner Records
$268,000Apr 2004 $7,2852024 Amount on Record Mar 1997 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

60 Chestnut Dr

3 bd · 2 ba · 1,120 sqft · 0.56 acres

Last Sale Tax Bill Prior Sale Owner Records
$179,900Jan 2017 $5,1922024 Amount on Record Oct 2015 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

63 Chestnut Dr

0.63 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,7072024 1 Name on Record AssessorUpdated Jul 2026

66 Chestnut Dr

3 bd · 1 ba · 1,560 sqft · 1.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,9072024 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

69 Chestnut Dr

3 bd · 1 ba · 1,314 sqft · 0.63 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,7302024 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

Property Records in Nearby Streets