Dempsey Way, Orlando, FL Property Records

Orange County property records for 50 addresses on Dempsey Way, Orlando, FL · Last verified October 2026

Dempsey Way Highlights

Properties 50
Median Sale Price $389,500
Deeds and Mortgages on File 46
Median Price per Sqft $246
Owner Occupied 78%
Median Annual Tax Bill $4,068
Median Year Built 1988
Median Ownership Tenure 11 years

Properties on Dempsey Way

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

100 Dempsey Way

4 bd · 2.5 ba · 2,070 sqft · built 1989 · 0.338 acres

Last Sale Tax Bill Prior Sale Owner Records
$130,000Apr 2001 $2,2582025 Owner on File Owner Occupied Assessor + 1 DocumentUpdated May 2026

101 Dempsey Way

3 bd · 2 ba · 1,688 sqft · built 1989 · 0.406 acres

Last Sale Tax Bill Prior Sale Owner Records
$38,400Dec 1998 $6,2252025 2 Owners on File Owner Occupied AssessorUpdated May 2026

106 Dempsey Way

4 bd · 2 ba · 1,846 sqft · built 1987 · 0.412 acres

Last Sale Tax Bill Prior Sale Owner Records
$159,900Feb 2004 $2,0352025 2 Owners on File Owner Occupied AssessorUpdated May 2026

107 Dempsey Way

3 bd · 2 ba · 1,524 sqft · built 1987 · 0.287 acres

Last Sale Tax Bill Prior Sale Owner Records
$240,000Sep 2005 $2,5222025 2 Owners on File Owner Occupied AssessorUpdated May 2026

113 Dempsey Way

3 bd · 2 ba · 1,416 sqft · built 1989 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,000May 2016 $2,8772025 Amount on File Dec 2008 Owner on File Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

119 Dempsey Way

4 bd · 2 ba · 1,846 sqft · built 1987 · 0.272 acres

Last Sale Tax Bill Prior Sale Owner Records
$310,000Sep 2019 $4,1112025 Amount on File Nov 2014 Owner on File Owner Occupied Assessor + 3 DocumentsUpdated Sep 2026

125 Dempsey Way

3 bd · 2 ba · 1,673 sqft · built 1988 · 0.37 acres

Last Sale Tax Bill Prior Sale Owner Records
$192,000Jul 2016 $3,8042025 Amount on File Nov 2004 Owner on File Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

131 Dempsey Way

4 bd · 2.5 ba · 2,070 sqft · built 1989 · 0.427 acres

Last Sale Tax Bill Prior Sale Owner Records
$129,900Jul 1998 $2,3642025 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated May 2026

137 Dempsey Way

3 bd · 2 ba · 1,497 sqft · built 1988 · 0.267 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,8232025 Owner on File Owner Occupied AssessorUpdated May 2026

138 Dempsey Way

3 bd · 2 ba · 1,636 sqft · built 1987 · 0.303 acres

Last Sale Tax Bill Prior Sale Owner Records
$199,600Jun 2005 $5,8782025 Amount on File Aug 2002 2 Owners on File AssessorUpdated May 2026

143 Dempsey Way

3 bd · 2 ba · 1,636 sqft · built 1989 · 0.235 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,8922025 Owner on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

144 Dempsey Way

3 bd · 2 ba · 1,200 sqft · built 1989 · 0.292 acres

Last Sale Tax Bill Prior Sale Owner Records
$116,000Feb 2013 $2,0222025 Amount on File Nov 2012 Owner on File Owner Occupied AssessorUpdated Sep 2026

149 Dempsey Way

2 bd · 2 ba · 1,545 sqft · built 1987 · 0.264 acres

Last Sale Tax Bill Prior Sale Owner Records
$89,900Sep 1998 $4,0142025 Owner on File Owner Occupied Assessor + 2 DocumentsUpdated May 2026

150 Dempsey Way

3 bd · 2 ba · 1,461 sqft · built 1987 · 0.299 acres

Last Sale Tax Bill Prior Sale Owner Records
$360,000Sep 2021 $4,8412025 Amount on File Dec 2005 Owner on File Owner Occupied Assessor + 1 DocumentUpdated May 2026

156 Dempsey Way

3 bd · 2 ba · 1,524 sqft · built 1988 · 0.244 acres

Last Sale Tax Bill Prior Sale Owner Records
$360,000Aug 2026 $6,1932025 Amount on File Nov 2016 Owner on File Assessor + 2 DocumentsUpdated Oct 2026

203 Dempsey Way

3 bd · 2 ba · 1,857 sqft · built 1987 · 0.264 acres

Last Sale Tax Bill Prior Sale Owner Records
$184,000Aug 2015 $3,0282025 Owner on File Owner Occupied AssessorUpdated May 2026

204 Dempsey Way

3 bd · 2 ba · 1,636 sqft · built 1988 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$51,500Jun 2000 $2,1832025 Amount on File Sep 1999 Owner on File Owner Occupied AssessorUpdated May 2026

209 Dempsey Way

4 bd · 2.5 ba · 1,683 sqft · built 1990 · 0.235 acres

Last Sale Tax Bill Prior Sale Owner Records
$216,000Jun 2017 $4,0352025 Amount on File Jun 2011 Owner on File Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

210 Dempsey Way

4 bd · 2.5 ba · 2,047 sqft · built 1990 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$216,000Jun 2016 $4,1762025 Amount on File Apr 2010 2 Owners on File Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

215 Dempsey Way

3 bd · 2 ba · 1,824 sqft · built 1989 · 0.235 acres

Last Sale Tax Bill Prior Sale Owner Records
$680,800Nov 2022 $7,0182025 Amount on File Jun 2021 Owner on File Assessor + 2 DocumentsUpdated Oct 2026

216 Dempsey Way

3 bd · 2 ba · 1,532 sqft · built 1987 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$121,500Feb 2002 $5,5252025 2 Owners on File Assessor + 2 DocumentsUpdated Sep 2026

221 Dempsey Way

3 bd · 2 ba · 1,636 sqft · built 1989 · 0.235 acres

Last Sale Tax Bill Prior Sale Owner Records
$143,000May 2003 $5,8512025 Owner on File Owner Occupied Assessor + 1 DocumentUpdated May 2026

222 Dempsey Way

3 bd · 2 ba · 1,497 sqft · built 1989 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$115,000Sep 2013 $2,8852025 —Jul 2013 Owner on File Owner Occupied AssessorUpdated Sep 2026

227 Dempsey Way

3 bd · 2 ba · 1,200 sqft · built 1989 · 0.235 acres

Last Sale Tax Bill Prior Sale Owner Records
$170,000Oct 2015 $5,2492025 Amount on File Jan 2009 2 Owners on File AssessorUpdated Sep 2026

228 Dempsey Way

3 bd · 2 ba · 1,532 sqft · built 1988 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$144,000Apr 2003 $1,8722025 Owner on File Owner Occupied AssessorUpdated May 2026

233 Dempsey Way

3 bd · 2 ba · 1,905 sqft · built 1989 · 0.235 acres

Last Sale Tax Bill Prior Sale Owner Records
$336,100Oct 2021 $6,6052025 Amount on File — Owner on File Assessor + 2 DocumentsUpdated Oct 2026

234 Dempsey Way

4 bd · 2 ba · 1,452 sqft · built 1989 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Dec 2018 $5,8802025 Amount on File Jun 2003 Owner on File Assessor + 3 DocumentsUpdated Sep 2026

239 Dempsey Way

3 bd · 2.5 ba · 1,910 sqft · built 1989 · 0.259 acres

Last Sale Tax Bill Prior Sale Owner Records
$410,000Apr 2026 $7,1642025 Amount on File Dec 2025 2 Owners on File Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

245 Dempsey Way

4 bd · 2 ba · 1,840 sqft · built 1989 · 0.384 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Apr 2024 $6,4272025 Amount on File Apr 2023 2 Owners on File Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

250 Dempsey Way

4 bd · 2 ba · 1,640 sqft · built 1987 · 0.268 acres

Last Sale Tax Bill Prior Sale Owner Records
$165,000Jul 2014 $5,4222025 —Mar 2005 Owner on File AssessorUpdated May 2026

251 Dempsey Way

3 bd · 2 ba · 1,584 sqft · built 1988 · 0.453 acres

Last Sale Tax Bill Prior Sale Owner Records
$410,000Jul 2023 $6,2932025 Amount on File Jan 2004 Owner on File Owner Occupied AssessorUpdated Oct 2026

257 Dempsey Way

3 bd · 2 ba · 1,629 sqft · built 1989 · 0.289 acres

Last Sale Tax Bill Prior Sale Owner Records
$390,000Nov 2022 $5,6832025 Amount on File May 2022 Owner on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

263 Dempsey Way

3 bd · 2 ba · 1,660 sqft · built 1989 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$123,500Mar 2013 $6,3402025 Amount on File Aug 2012 Owner on File Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

269 Dempsey Way

3 bd · 2 ba · 1,658 sqft · built 1989 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000Jan 2017 $3,5022025 Amount on File Aug 2008 Owner on File Owner Occupied Assessor + 5 DocumentsUpdated Sep 2026

305 Dempsey Way

3 bd · 2 ba · 1,501 sqft · built 1989 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,000Jul 2005 $1,8492025 —Nov 2001 Owner on File Owner Occupied AssessorUpdated May 2026

311 Dempsey Way

3 bd · 2 ba · 1,665 sqft · built 1989 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$100,000Dec 2014 $2,6262025 2 Owners on File Owner Occupied AssessorUpdated May 2026

317 Dempsey Way

3 bd · 2 ba · 1,636 sqft · built 1989 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,7242025 2 Owners on File Owner Occupied AssessorUpdated May 2026

318 Dempsey Way

3 bd · 2 ba · 1,697 sqft · built 1988 · 0.257 acres

Last Sale Tax Bill Prior Sale Owner Records
$145,000Jul 2003 $2,0362025 Amount on File Apr 2001 2 Owners on File Owner Occupied AssessorUpdated May 2026

323 Dempsey Way

3 bd · 2 ba · 1,480 sqft · built 1987 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$389,500Oct 2023 $5,4232025 Amount on File Jun 2007 Owner on File Assessor + 1 DocumentUpdated Oct 2026

324 Dempsey Way

3 bd · 2 ba · 1,636 sqft · built 1988 · 0.279 acres

Last Sale Tax Bill Prior Sale Owner Records
$332,000Aug 2021 $5,0552025 Amount on File Oct 2014 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

329 Dempsey Way

3 bd · 2 ba · 1,655 sqft · built 1988 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$105,000Sep 1994 $1,9072025 2 Owners on File Owner Occupied AssessorUpdated May 2026

335 Dempsey Way

3 bd · 2 ba · 1,532 sqft · built 1987 · 0.295 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,8422025 Owner on File Owner Occupied AssessorUpdated May 2026

341 Dempsey Way

3 bd · 2 ba · 1,488 sqft · built 1988 · 0.291 acres

Last Sale Tax Bill Prior Sale Owner Records
$242,500Feb 2007 $1,7552025 Amount on File Aug 2005 2 Owners on File Owner Occupied AssessorUpdated May 2026

342 Dempsey Way

3 bd · 2 ba · 1,416 sqft · built 1988 · 0.314 acres

Last Sale Tax Bill Prior Sale Owner Records
$105,000Dec 1999 $1,7552025 Amount on File Jul 1998 Owner on File Owner Occupied Assessor + 1 DocumentUpdated May 2026

347 Dempsey Way

3 bd · 2 ba · 1,760 sqft · built 1988 · 0.257 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,700Dec 2024 $6,6542025 Amount on File Feb 2023 Owner on File AssessorUpdated Aug 2026

353 Dempsey Way

3 bd · 2 ba · 1,497 sqft · built 1988 · 0.235 acres

Last Sale Tax Bill Prior Sale Owner Records
$370,000Feb 2023 $5,9242025 Amount on File Mar 2022 Owner on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

354 Dempsey Way

3 bd · 2 ba · 1,828 sqft · built 1989 · 0.247 acres

Last Sale Tax Bill Prior Sale Owner Records
$144,000Mar 2014 $6,1192025 Amount on File Nov 2011 2 Owners on File Owner Occupied AssessorUpdated May 2026

359 Dempsey Way

3 bd · 2.5 ba · 2,022 sqft · built 1988 · 0.235 acres

Last Sale Tax Bill Prior Sale Owner Records
$220,000Oct 2015 $4,0682025 2 Owners on File Owner Occupied AssessorUpdated May 2026

365 Dempsey Way

3 bd · 2 ba · 1,491 sqft · built 1988 · 0.235 acres

Last Sale Tax Bill Prior Sale Owner Records
$52,000Mar 2018 $5,5792025 Amount on File Jan 2007 Owner on File Assessor + 1 DocumentUpdated Sep 2026

371 Dempsey Way

4 bd · 2.5 ba · 2,070 sqft · built 1988 · 0.434 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,3752025 Owner on File Owner Occupied Assessor + 1 DocumentUpdated May 2026

Property Records in Nearby Streets