Chestnut St, Winsted, CT Property Records

Winchester Town property records for 21 addresses on Chestnut St, Winsted, CT · Last verified July 2026

Chestnut St Highlights

Properties 21
Median Sale Price $135,000
Deeds and Mortgages on File 23
Median Price per Sqft $66
Owner Occupied 29%
Median Annual Tax Bill $2,928
Median Year Built 1900
Median Ownership Tenure 7 years

Properties on Chestnut St

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

5 Chestnut St

6 bd · 3 ba · 3,450 sqft · 0.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$50,000Jul 2014 $2,2182025 1 Name on Record AssessorUpdated Jul 2026

7 Chestnut St

6 bd · 4 ba · 3,172 sqft · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$38,333Aug 2021 $3,0402025 Amount on Record — 1 Name on Record Assessor + 3 DocumentsUpdated Jul 2026

8 Chestnut St

3 bd · 2 ba · 1,250 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$94,900Jun 1999 $3942025 Amount on Record Apr 1993 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

11 Chestnut St

3 bd · 2 ba · 1,278 sqft · 0.089 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$76,667Aug 2021 $1942025 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

12 Chestnut St

3 bd · 2 ba · 2,019 sqft · 0.15 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$122,000Sep 2019 $3,7882025 —Sep 2019 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

14 Chestnut St

4 bd · 2 ba · 1,560 sqft · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$85,000Jun 2018 $2,3912025 Amount on Record Jun 2011 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

16 Chestnut St

8 bd · 3 ba · 3,298 sqft · 0.289 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$55,000Oct 2014 $3,1732025 2 Names on Record AssessorUpdated Jul 2026

17 Chestnut St

5 bd · 2 ba · 1,932 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$243,000Jul 2024 $3,0082025 Amount on Record May 2018 1 Name on Record Assessor + 3 DocumentsUpdated Jul 2026

19 Chestnut St

4 bd · 2 ba · 2,282 sqft · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$50,500May 2020 $2,6182025 —Jun 2019 1 Name on Record Assessor + 5 DocumentsUpdated Jul 2026

25 Chestnut St

4 bd · 2 ba · 1,572 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$160,000Apr 1993 $2,9282025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

31 Chestnut St

8 bd · 4 ba · 2,600 sqft · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,6572025 1 Name on Record AssessorUpdated Jul 2026

33 Chestnut St

6 bd · 2 ba · 2,032 sqft · 0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
—Sep 2023 $3,5302025 Amount on Record Nov 2021 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

37 Chestnut St, #39

4 bd · 2 ba · 1,700 sqft · 0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000Apr 2021 $2,1852025 Amount on Record Dec 2010 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

43 Chestnut St

0.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,000Sep 2013 $3532025 Amount on Record Feb 1987 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

51 Chestnut St, #53

6 bd · 3 ba · 2,155 sqft · 0.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$197,500Apr 2024 $932025 Amount on Record Mar 2007 1 Name on Record Assessor + 2 DocumentsUpdated Jul 2026

59 Chestnut St

7 bd · 3 ba · 2,016 sqft · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$135,000Apr 2023 $3,8592024 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

65 Chestnut St

4 bd · 2 ba · 2,138 sqft · 0.169 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,1082025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

67 Chestnut St

4 bd · 2 ba · 1,550 sqft · 0.189 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,3322025 1 Name on Record AssessorUpdated Jul 2026

79 Chestnut St

9 bd · 6 ba · 4,896 sqft · 0.35 acres

Last Sale Tax Bill Prior Sale Owner Records
$260,000Feb 2008 $7,3882025 Amount on Record Aug 2005 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

80 Chestnut St

50,068 sqft · Built 1971 · 1.96 acres

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

86 Chestnut St

4 bd · 2 ba · 1,561 sqft · 0.119 acres

Last Sale Tax Bill Prior Sale Owner Records
$92,500Nov 2001 $3,5962025 Amount on Record Nov 1999 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

Property Records in Nearby Streets