Oak St, Winsted, CT Property Records

Winchester Town property records for 63 addresses on Oak St, Winsted, CT · Last verified August 2026

Oak St Highlights

Properties 63
Median Sale Price $225,000
Deeds and Mortgages on File 60
Median Price per Sqft $93
Owner Occupied 78%
Median Annual Tax Bill $3,545
Median Year Built 1898
Median Ownership Tenure 11 years

Properties on Oak St

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

8 Oak St

2 bd · 1 ba · 832 sqft · 0.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$154,600Mar 2026 $1,8192025 Amount on Record Feb 2021 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

10 Oak St

4 bd · 2 ba · 1,393 sqft · 0.089 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,2772025 1 Name on Record AssessorUpdated Jul 2026

20 Oak St

7 bd · 2.5 ba · 2,340 sqft · 0.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$150,000Dec 2024 $2,8012025 Amount on Record Jun 2014 1 Name on Record Assessor + 3 DocumentsUpdated Jul 2026

21 Oak St

0.119 acres

Last Sale Tax Bill Prior Sale Owner Records
$6112025 1 Name on Record AssessorUpdated Jul 2026

26 Oak St

4 bd · 2 ba · 1,808 sqft · 0.169 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$109,000Dec 2015 $2,9282025 Amount on Record Nov 2012 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

28 Oak St

2 bd · 1.5 ba · 1,715 sqft · 0.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,1832025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

30 Oak St

3 bd · 1 ba · 1,272 sqft · 0.18 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$137,900Aug 2018 $2,9872025 Amount on Record Jul 1990 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

31 Oak St

5.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000Aug 2021 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

32 Oak St

4 bd · 1.5 ba · 2,320 sqft · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,2142025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

40 Oak St

3 bd · 1.5 ba · 1,674 sqft · 0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Aug 2023 $3,9392025 Amount on Record Aug 2017 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

44 Oak St

3 bd · 1 ba · 1,190 sqft · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$94,000Apr 2002 $2,0072025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

46 Oak St

4 bd · 2 ba · 2,336 sqft · 0.119 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$46,219Jun 2024 $3,5452025 Amount on Record Nov 2022 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

54 Oak St

4 bd · 1.5 ba · 2,257 sqft · 0.189 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$65,500Jan 2019 $3,0962025 —Jul 2017 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

60 Oak St

0.13 acres

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

66 Oak St

5 bd · 2 ba · 2,610 sqft · 0.35 acres

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

79 Oak St

3 bd · 1.5 ba · 1,476 sqft · 0.26 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$119,000Jul 2017 $3,6042025 Amount on Record Jul 2009 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

80 Oak St

2 bd · 1 ba · 1,132 sqft · 0.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$158,000Sep 2006 $3,1612025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

81 Oak St

3 bd · 2.5 ba · 1,488 sqft · 0.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$128,800Aug 2016 $3,2322025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

85 Oak St

3 bd · 1 ba · 1,104 sqft · 0.61 acres

Last Sale Tax Bill Prior Sale Owner Records
$315,000Jun 2025 $6,0732025 Amount on Record Apr 2019 2 Names on Record Assessor + 3 DocumentsUpdated Jul 2026

106 Oak St, #108

5 bd · 2 ba · 1,500 sqft · 0.119 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000Jan 2009 $3,6062024 1 Name on Record AssessorUpdated Jul 2026

114 Oak St

3 bd · 1.5 ba · 2,192 sqft · 0.289 acres

Last Sale Tax Bill Prior Sale Owner Records
$275,000Jun 2024 $5,7382024 Amount on Record Apr 1992 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

118 Oak St

3 bd · 2 ba · 1,606 sqft · 0.189 acres

Last Sale Tax Bill Prior Sale Owner Records
$139,900Feb 2016 $3,6022025 Amount on Record Mar 2010 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

149 Oak St

6 bd · 2.5 ba · 3,517 sqft · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
$130,500Oct 2001 $4,4372025 Amount on Record Jun 1995 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

150 Oak St

9 bd · 5 ba · 5,233 sqft · 0.189 acres

Last Sale Tax Bill Prior Sale Owner Records
$341,000Aug 2021 $6,7062025 —Aug 2021 1 Name on Record Assessor + 2 DocumentsUpdated Jul 2026

153 Oak St

3 bd · 2 ba · 1,728 sqft · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,5632025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

156 Oak St

0.369 acres

Last Sale Tax Bill Prior Sale Owner Records
$7272025 1 Name on Record AssessorUpdated Jul 2026

159 Oak St

4 bd · 2.5 ba · 1,620 sqft · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$258,000Nov 2021 $4,2612025 Amount on Record Mar 2021 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

160 Oak St

4 bd · 3.5 ba · 2,468 sqft · 0.239 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$190,000Oct 2009 $4,6412025 Amount on Record May 2000 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

165 Oak St

4 bd · 2 ba · 1,761 sqft · 0.289 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$165,000May 2023 $3,7512025 Amount on Record Jun 2008 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

171 Oak St

2 bd · 1 ba · 768 sqft · 0.28 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$145,000Aug 2005 $2,4602025 Amount on Record Apr 2005 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

177 Oak St

1 bd · 1 ba · 768 sqft · 0.28 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,7032025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

180 Oak St

4 bd · 2.5 ba · 1,562 sqft · 0.889 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4,3882025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

191 Oak St

4 bd · 2 ba · 1,449 sqft · 0.28 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$100,000Aug 2000 $3,4282025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

197 Oak St

3 bd · 1 ba · 1,354 sqft · 0.28 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$140,000Feb 2008 $3,4612025 Amount on Record May 2007 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

198 Oak St

4 bd · 2 ba · 2,172 sqft · 0.319 acres

Last Sale Tax Bill Prior Sale Owner Records
$182,000Dec 2007 $4,0432025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

201 Oak St

3 bd · 1 ba · 1,114 sqft · 0.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$12,000Apr 2023 $3,3002025 Amount on Record Oct 2020 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

202 Oak St

3 bd · 1.5 ba · 1,444 sqft · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$66,500Jan 2001 $2,4262025 Amount on Record Mar 1996 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

206 Oak St

3 bd · 1 ba · 1,444 sqft · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,7262025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

207 Oak St

4 bd · 1 ba · 1,114 sqft · 0.419 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$145,000Aug 2003 $3,4962025 Amount on Record Sep 1999 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

210 Oak St

3 bd · 1 ba · 2,010 sqft · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$170,000Jul 2008 $3,0202025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

214 Oak St

3 bd · 1 ba · 1,765 sqft · 0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$157,000Aug 2009 $2,8552025 Amount on Record Mar 2002 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

215 Oak St

2 bd · 1 ba · 1,392 sqft · 0.319 acres

Last Sale Tax Bill Prior Sale Owner Records
$120,000Sep 1992 $4,3432025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

218 Oak St

3 bd · 1 ba · 1,155 sqft · 0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$78,000Jul 2005 $2,4812025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

221 Oak St

4 bd · 1.5 ba · 2,121 sqft · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,1232025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

222 Oak St

4 bd · 4 ba · 2,742 sqft · 0.18 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$138,000Oct 1997 $4,8882025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

229 Oak St

2 bd · 1 ba · 1,120 sqft · 0.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$120,500Jan 2015 $3,0612025 —Dec 2014 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

230 Oak St

4 bd · 2 ba · 1,772 sqft · 0.369 acres

Last Sale Tax Bill Prior Sale Owner Records
$160,000Aug 2024 $3,2222025 Amount on Record Jan 2018 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

233 Oak St

4 bd · 2 ba · 1,868 sqft · 0.25 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$96,000May 2001 $4,0922025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

234 Oak St

3 bd · 2 ba · 1,302 sqft · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Jan 2024 $3,6002025 Amount on Record Mar 2016 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

237 Oak St

4 bd · 2 ba · 1,728 sqft · 0.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,1242025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

240 Oak St

3 bd · 2 ba · 1,414 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$205,000Oct 2004 $4,0182025 Amount on Record Aug 2000 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

243 Oak St

5 bd · 3 ba · 2,832 sqft · 0.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$147,000Nov 2011 $4,2392025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

246 Oak St

4 bd · 3 ba · 2,328 sqft · 0.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$35,000Dec 2015 $3,5922025 Amount on Record Sep 2010 1 Name on Record Assessor + 2 DocumentsUpdated Aug 2026

249 Oak St

6 bd · 3 ba · 2,148 sqft · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,0782025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

250 Oak St

2 bd · 1 ba · 1,302 sqft · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$45,000May 1998 $2,7142025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

258 Oak St

6 bd · 2.5 ba · 2,102 sqft · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
$160,000Jun 2018 $4,8582025 Amount on Record Jul 1996 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

259 Oak St

4 bd · 3 ba · 2,153 sqft · 0.3 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$5,1092025 2 Names on Record AssessorUpdated Jul 2026

261 Oak St

4 bd · 3 ba · 2,646 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$143,000May 2020 $6,1562025 Amount on Record Dec 2017 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Aug 2026

262 Oak St

4 bd · 2.5 ba · 1,905 sqft · 0.35 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$102,000Sep 1997 $4,3572025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

266 Oak St

4 bd · 2 ba · 1,512 sqft · 0.219 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$111,000Mar 2012 $3,7372025 Amount on Record Aug 2003 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

267 Oak St

5 bd · 2 ba · 2,168 sqft · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$73,102Oct 2019 $2,6732025 —Jul 2019 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

273 Oak St, #275

6 bd · 2 ba · 2,292 sqft · 0.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$162,000Jun 2010 $4,0252025 Amount on Record Jun 1987 2 Names on Record AssessorUpdated Jul 2026

275 Oak St

1.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$4512025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

Property Records in Nearby Streets