Windermere Dr, Middlesboro, KY Property Records

Bell County property records for 31 addresses on Windermere Dr, Middlesboro, KY · Last verified August 2026

Windermere Dr Highlights

Properties 31
Median Sale Price $225,000
Deeds and Mortgages on File 36
Median Price per Sqft $119
Owner Occupied 77%
Median Annual Tax Bill $1,880
Median Year Built 2002
Median Ownership Tenure 9 years

Properties on Windermere Dr

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

202 Windermere Dr

1,252 sqft · built 1998

Last Sale Tax Bill Prior Sale Owner Records
$135,000Dec 2010 $1,6112025 Owner on Record Owner Occupied AssessorUpdated Dec 2025

204 Windermere Dr

1,262 sqft · built 1998

Last Sale Tax Bill Prior Sale Owner Records
$134,000Apr 2010 $1,5992025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

206 Windermere Dr

1,098 sqft · built 2002

Last Sale Tax Bill Prior Sale Owner Records
$85,500Dec 2020 $1,0202025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

208 Windermere Dr

2,465 sqft · built 1998

Last Sale Tax Bill Prior Sale Owner Records
$168,000Jan 2020 $2,0052025 Amount on Record Mar 2019 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

210 Windermere Dr

1,402 sqft · built 2000

Last Sale Tax Bill Prior Sale Owner Records
$135,000Dec 2016 $1,6112025 Owner on Record Owner Occupied AssessorUpdated Dec 2025

211 Windermere Dr, #II

1,944 sqft · built 1999

Last Sale Tax Bill Prior Sale Owner Records
$190,000Jul 2010 $2,2682025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

212 Windermere Dr

1,476 sqft · built 2001

Last Sale Tax Bill Prior Sale Owner Records
$199,900Jan 2024 $2,3862025 Amount on Record Mar 2022 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

213 Windermere Dr

2 ba · 1,328 sqft · built 2000

Last Sale Tax Bill Prior Sale Owner Records
$122,500May 2012 $8762025 Owner on Record Owner Occupied AssessorUpdated Dec 2025

214 Windermere Dr

1,706 sqft · built 2002

Last Sale Tax Bill Prior Sale Owner Records
$155,000Oct 2015 $1,2642025 Owner on Record Owner Occupied AssessorUpdated Dec 2025

215 Windermere Dr

2,633 sqft · built 2001

Last Sale Tax Bill Prior Sale Owner Records
$285,000Jun 2023 $3,4022025 Amount on Record Mar 2019 2 Owners on Record Owner Occupied Assessor + 5 DocumentsUpdated Apr 2026

216 Windermere Dr

1,570 sqft · built 2002

Last Sale Tax Bill Prior Sale Owner Records
$157,590Oct 2016 $1,8802025 —Sep 2016 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026
Last Sale Tax Bill Prior Sale Owner Records
$32,500Mar 2026 2 Owners on Record Assessor + 1 DocumentUpdated Apr 2026

218 Windermere Dr

1,296 sqft · built 2002

Last Sale Tax Bill Prior Sale Owner Records
$225,000Aug 2025 $2,0292025 Amount on Record Jul 2021 2 Owners on Record Assessor + 3 DocumentsUpdated Apr 2026
Last Sale Tax Bill Prior Sale Owner Records
$32,500Mar 2026 $5372025 2 Owners on Record Assessor + 1 DocumentUpdated Apr 2026

220 Windermere Dr

1,692 sqft · built 2003

Last Sale Tax Bill Prior Sale Owner Records
$240,000Feb 2026 $1,2102025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

221 Windermere Dr

4 bd · 4 ba · 4,070 sqft · built 2007

Last Sale Tax Bill Prior Sale Owner Records
$211,600Jul 2007 $2,5262025 Owner on Record Owner Occupied Assessor + 5 DocumentsUpdated Aug 2026

222 Windermere Dr

1,184 sqft · built 2003

Last Sale Tax Bill Prior Sale Owner Records
$193,266Jul 2026 $5952025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
$24,000Jul 2007 $2862025 2 Owners on Record AssessorUpdated Dec 2025

224 Windermere Dr

2,344 sqft · built 2004

Last Sale Tax Bill Prior Sale Owner Records
—Feb 2024 $2,3282025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

225 Windermere Dr

3,351 sqft · built 2002

Last Sale Tax Bill Prior Sale Owner Records
$24,500Jul 2002 $1,3832025 2 Owners on Record Owner Occupied AssessorUpdated Dec 2025

226 Windermere Dr

3 bd · 2 ba · 1,680 sqft · built 2004

Last Sale Tax Bill Prior Sale Owner Records
$8,000Dec 2017 $1,7912025 Amount on Record Feb 2014 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

227 Windermere Dr

3 bd · 2 ba · 2,764 sqft · built 2002

Last Sale Tax Bill Prior Sale Owner Records
$275,000Sep 2022 $2,6972025 Amount on Record Jun 2022 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

228 Windermere Dr

1,382 sqft · built 2005

Last Sale Tax Bill Prior Sale Owner Records
$162,500Nov 2005 $1,3542025 Owner on Record Owner Occupied AssessorUpdated Dec 2025

229 Windermere Dr

3,654 sqft · built 2006 · 0.453 acres

Last Sale Tax Bill Prior Sale Owner Records
$227,000Mar 2017 $2,7102025 Amount on Record Jul 2006 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

230 Windermere Dr

3 bd · 2 ba · 2,099 sqft · built 2007

Last Sale Tax Bill Prior Sale Owner Records
$250,000May 2025 $2,6502025 Amount on Record Aug 2022 2 Owners on Record Assessor + 2 DocumentsUpdated Dec 2025
Last Sale Tax Bill Prior Sale Owner Records
—Jan 2018 $2082025 Amount on Record May 2007 Owner on Record AssessorUpdated Dec 2025

234 Windermere Dr

2,080 sqft · built 2003

Last Sale Tax Bill Prior Sale Owner Records
$170,000Aug 2005 $2,5072025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

236 Windermere Dr

3 bd · 2 ba · 2,254 sqft · built 2002

Last Sale Tax Bill Prior Sale Owner Records
$180,000Jan 2008 $2,6912025 —Jan 2008 Owner on Record Owner Occupied AssessorUpdated Dec 2025

238 Windermere Dr

2,494 sqft · built 2001

Last Sale Tax Bill Prior Sale Owner Records
$161,500Oct 2001 $2,0892025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025
Last Sale Tax Bill Prior Sale Owner Records
$265,000Aug 2025 $2742025 Amount on Record Mar 2014 2 Owners on Record AssessorUpdated Dec 2025

242 Windermere Dr

2,910 sqft · built 2001

Last Sale Tax Bill Prior Sale Owner Records
$265,000May 2022 $3,1642025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

Property Records in Nearby Streets