Cheshire Way, Naples, FL Property Records

Collier County property records for 59 addresses on Cheshire Way, Naples, FL · Last verified October 2026

Cheshire Way Highlights

Properties 59
Median Sale Price $1,900,000
Deeds and Mortgages on File 78
Median Price per Sqft $454
Owner Occupied 83%
Median Annual Tax Bill $15,270
Median Year Built 2000
Median Ownership Tenure 8 years

Properties on Cheshire Way

Owner names and exact recorded amounts are on file and can be viewed instantly on this page with a free 10-day trial.

140 Cheshire Way

3,897 sqft · built 1997 · 0.38 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,525,000Aug 2025 $19,7402025 Amount on Record Oct 2021 2 Owners on Record Assessor + 3 DocumentsUpdated Sep 2026

141 Cheshire Way

4,260 sqft · built 2004 · 0.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,417,000Dec 2012 $13,2952025 Amount on Record Jun 2002 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

144 Cheshire Way

4,991 sqft · built 1997 · 0.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,400,000Feb 2021 $22,6672025 Amount on Record Aug 2001 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

145 Cheshire Way

4,348 sqft · built 2023 · 0.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,350,000Feb 2024 $31,3562025 Amount on Record Nov 2022 2 Owners on Record Assessor + 2 DocumentsUpdated Sep 2026

148 Cheshire Way

3,770 sqft · built 1995 · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,295,000Apr 2017 $9,1642025 Amount on Record Jan 2014 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

151 Cheshire Way

3,787 sqft · built 1997 · 0.419 acres

Last Sale Tax Bill Prior Sale Owner Records
$935,000May 2001 $9,0332025 Amount on Record Oct 1997 2 Owners on Record Owner Occupied AssessorUpdated Sep 2026

152 Cheshire Way

3,654 sqft · built 1999 · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$215,000Apr 1998 $6,7582025 —Jun 1999 Owner on Record Owner Occupied AssessorUpdated Sep 2026

155 Cheshire Way

4,264 sqft · built 1995 · 0.419 acres

Last Sale Tax Bill Prior Sale Owner Records
$990,000Jun 2020 $17,7902025 Amount on Record Aug 2015 Owner on Record Assessor + 1 DocumentUpdated Sep 2026

156 Cheshire Way

4,374 sqft · built 2000 · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000May 1999 $11,1792025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

159 Cheshire Way

4,362 sqft · built 1998 · 0.419 acres

Last Sale Tax Bill Prior Sale Owner Records
$800,000Jun 2020 $17,9442025 Amount on Record Jan 1996 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

160 Cheshire Way

5,066 sqft · built 2001 · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,680,000Dec 2015 $25,8622025 Amount on Record Apr 2014 Owner on Record Owner Occupied AssessorUpdated Sep 2026

163 Cheshire Way

3,475 sqft · built 1996 · 0.419 acres

Last Sale Tax Bill Prior Sale Owner Records
$710,000Mar 2011 $14,4612025 Amount on Record Apr 1996 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

164 Cheshire Way

3,886 sqft · built 1995 · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$850,000Mar 2014 $9,2382025 Amount on Record Oct 1997 2 Owners on Record Owner Occupied AssessorUpdated Sep 2026

167 Cheshire Way

4,070 sqft · built 1996 · 0.419 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Oct 1995 $8,7662025 Owner on Record Owner Occupied AssessorUpdated Sep 2026

168 Cheshire Way

4,366 sqft · built 1998 · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$995,000Jun 2012 $10,7442025 —May 2004 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

171 Cheshire Way

3,889 sqft · built 2000 · 0.419 acres

Last Sale Tax Bill Prior Sale Owner Records
$240,000Apr 1998 $12,4732025 2 Owners on Record Owner Occupied AssessorUpdated Sep 2026

172 Cheshire Way

3,904 sqft · built 1998 · 0.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,850,000Sep 2024 $23,3702025 Amount on Record Oct 2020 2 Owners on Record Owner Occupied Assessor + 7 DocumentsUpdated Sep 2026

175 Cheshire Way

3,732 sqft · built 2000 · 0.419 acres

Last Sale Tax Bill Prior Sale Owner Records
$950,000Mar 2020 $9,6572025 Amount on Record Apr 2002 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

176 Cheshire Way

4,373 sqft · built 2007 · 0.539 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,560,000Jul 2015 $11,6472025 Amount on Record May 2014 Owner on Record Owner Occupied AssessorUpdated Sep 2026

179 Cheshire Way

3,712 sqft · built 1997 · 0.419 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,550,000Nov 2025 $6,5322025 Amount on Record Mar 2017 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

180 Cheshire Way

3,766 sqft · built 2012 · 0.45 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,625,000Dec 2018 $16,2392025 Amount on Record Jun 2010 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2026

184 Cheshire Way

3,842 sqft · built 2002 · 0.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$970,000Aug 2014 $10,4792025 Amount on Record Jul 2001 2 Owners on Record Owner Occupied AssessorUpdated Sep 2026

185 Cheshire Way

3,915 sqft · built 1996 · 0.439 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,000,000Aug 2021 $23,3092025 Amount on Record Jan 1994 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

188 Cheshire Way

3,960 sqft · built 2000 · 0.369 acres

Last Sale Tax Bill Prior Sale Owner Records
$950,400Jun 2000 $9,4302025 Amount on Record Apr 1999 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

191 Cheshire Way

4,465 sqft · built 1996 · 0.469 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,350,000Sep 2023 $19,4972025 Amount on Record May 2016 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

192 Cheshire Way

4,110 sqft · built 1996 · 0.36 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Jan 1996 $16,1172025 Owner on Record Assessor + 1 DocumentUpdated Sep 2026

195 Cheshire Way

4,477 sqft · built 2018 · 0.43 acres

Last Sale Tax Bill Prior Sale Owner Records
$475,000Jul 2016 $23,3202025 Amount on Record May 2016 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

196 Cheshire Way

3,885 sqft · built 2000 · 0.36 acres

Last Sale Tax Bill Prior Sale Owner Records
$220,000Dec 1998 $15,8132025 —Dec 1998 Owner on Record Owner Occupied AssessorUpdated Oct 2026

199 Cheshire Way

3,911 sqft · built 1999 · 0.419 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,750,000May 2024 $15,8402025 Amount on Record Mar 1999 2 Owners on Record Owner Occupied AssessorUpdated Sep 2026

200 Cheshire Way

3,982 sqft · built 1999 · 0.36 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Apr 1999 $9,1902025 —Apr 1999 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

204 Cheshire Way

4,019 sqft · built 2000 · 0.38 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,825,000Oct 2021 $17,1092025 Amount on Record May 2003 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

207 Cheshire Way

3,947 sqft · built 2008 · 0.419 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,275,000Sep 2018 $11,7332025 Amount on Record Feb 2011 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

208 Cheshire Way

3,441 sqft · built 2002 · 0.419 acres

Last Sale Tax Bill Prior Sale Owner Records
$840,000Aug 2013 $8,7922025 Amount on Record Aug 2001 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

211 Cheshire Way

4,144 sqft · built 2003 · 0.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,695,000Apr 2019 $23,3672025 Amount on Record May 1999 Owner on Record Assessor + 1 DocumentUpdated Sep 2026

212 Cheshire Way

3,151 sqft · built 1995 · 0.419 acres

Last Sale Tax Bill Prior Sale Owner Records
$850,000Jul 2004 $7,5992025 Amount on Record Aug 1994 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

216 Cheshire Way

4,574 sqft · built 2000 · 0.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,375,000Nov 2021 $25,5262025 Amount on Record Jun 2018 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

219 Cheshire Way

3,998 sqft · built 2005 · 0.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,295,000Aug 2023 $24,6072025 Amount on Record Mar 2002 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

223 Cheshire Way

4,220 sqft · built 2003 · 0.43 acres

Last Sale Tax Bill Prior Sale Owner Records
$255,000Mar 2001 $11,2202025 Owner on Record Owner Occupied AssessorUpdated Sep 2026

227 Cheshire Way

3,928 sqft · built 2006 · 0.43 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,300,000Apr 2020 $18,7222025 Amount on Record May 2015 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

228 Cheshire Way

3,521 sqft · built 2024 · 0.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$625,000Jul 2021 $25,6302025 Amount on Record Nov 2002 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

232 Cheshire Way

3,369 sqft · built 2023 · 0.369 acres

Last Sale Tax Bill Prior Sale Owner Records
$625,000Sep 2021 $25,7222025 Amount on Record May 1998 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

235 Cheshire Way

4,578 sqft · built 1993 · 0.439 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,900,000Jun 2021 $23,4912025 Amount on Record Jun 2018 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2026

236 Cheshire Way

4,087 sqft · built 2003 · 0.4 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 2001 $12,2892025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

240 Cheshire Way

4,186 sqft · built 2015 · 0.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$385,000Mar 2012 $12,6262025 Amount on Record May 2001 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

244 Cheshire Way

4,152 sqft · built 1998 · 0.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$870,000Nov 2018 $10,3262025 Amount on Record Dec 1997 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Sep 2026

245 Cheshire Way

4,235 sqft · built 1995 · 0.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,650,000Oct 2022 $19,8842025 Amount on Record Apr 2002 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

248 Cheshire Way

3,329 sqft · built 1996 · 0.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,950,000May 2024 $19,7072025 Amount on Record May 2021 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Sep 2026

249 Cheshire Way

3,905 sqft · built 1995 · 0.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,105,000Oct 2003 $9,8002025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

252 Cheshire Way

3,900 sqft · built 1995 · 0.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,100,000Nov 2015 $17,9922025 Owner on Record AssessorUpdated Sep 2026

253 Cheshire Way

4,545 sqft · built 2002 · 0.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,600,000Apr 2026 $24,3392025 Amount on Record Apr 2022 Owner on Record Owner Occupied Assessor + 6 DocumentsUpdated Sep 2026

256 Cheshire Way

3,306 sqft · built 1999 · 0.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,320,000Oct 2019 $10,6582025 Amount on Record Sep 2014 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

257 Cheshire Way

4,073 sqft · built 2000 · 0.419 acres

Last Sale Tax Bill Prior Sale Owner Records
$240,000Mar 1998 $10,1932025 Owner on Record Owner Occupied AssessorUpdated Sep 2026

260 Cheshire Way

3,272 sqft · built 2001 · 0.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Apr 1999 $21,7212025 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

263 Cheshire Way

4,122 sqft · built 1997 · 0.45 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,230,000Feb 2023 $21,5112025 Amount on Record Jul 2005 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

264 Cheshire Way

3,690 sqft · built 2004 · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,062,500Mar 2020 $16,5712025 Amount on Record Feb 2013 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

267 Cheshire Way

4,730 sqft · built 1998 · 0.45 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,095,000Oct 2018 $19,8082025 —May 1997 2 Owners on Record Assessor + 1 DocumentUpdated Sep 2026

268 Cheshire Way

3,853 sqft · built 2005 · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,000,000Jun 2020 $10,7112025 Amount on Record Jun 2014 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

272 Cheshire Way

4,041 sqft · built 2004 · 0.369 acres

Last Sale Tax Bill Prior Sale Owner Records
$325,000May 2022 $20,4572025 Amount on Record Jul 2010 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2026

275 Cheshire Way

3,345 sqft · built 2000 · 0.88 acres

Last Sale Tax Bill Prior Sale Owner Records
$100Sep 2016 $10,7912025 —Aug 2016 Owner on Record Owner Occupied AssessorUpdated Sep 2026

Property Records in Nearby Streets