Harbor Dr, Winter Garden, FL Property Records

Orange County property records for 27 addresses on Harbor Dr, Winter Garden, FL · Last verified July 2026

Harbor Dr Highlights

Properties 27
Median Sale Price $525,000
Deeds and Mortgages on File 33
Median Price per Sqft $303
Owner Occupied 78%
Median Annual Tax Bill $3,022
Median Year Built 1989
Median Ownership Tenure 9 years

Properties on Harbor Dr

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

200 Harbor Dr

4 bd · 2 ba · 1,994 sqft · 0.377 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,3312025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

201 Harbor Dr

3 bd · 2 ba · 1,555 sqft · 0.356 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$205,000May 2015 $3,0242025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

204 Harbor Dr

3 bd · 2 ba · 1,522 sqft · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$190,000Jul 2005 $2,3052025 1 Name on Record AssessorUpdated May 2026

205 Harbor Dr

3 bd · 2 ba · 1,719 sqft · 0.253 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$540,000Jul 2024 $6,8752025 Amount on Record Jun 2015 2 Names on Record Assessor + 4 DocumentsUpdated May 2026

208 Harbor Dr

4 bd · 2 ba · 1,524 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$525,000Mar 2023 $6,0912025 Amount on Record Apr 2022 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

209 Harbor Dr

3 bd · 2 ba · 1,514 sqft · 0.231 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$22,600Dec 2019 $2,0672025 Amount on Record Dec 2012 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

212 Harbor Dr

3 bd · 2 ba · 1,568 sqft · 0.255 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$100Apr 2021 $1,9802025 Amount on Record Apr 1998 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

213 Harbor Dr

3 bd · 2 ba · 1,750 sqft · 0.229 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2011 $3,0222025 Amount on Record Aug 2003 1 Name on Record Owner Occupied AssessorUpdated May 2026

216 Harbor Dr

3 bd · 2 ba · 1,781 sqft · 0.234 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$540,000Feb 2026 $7,7332025 Amount on Record Sep 2022 2 Names on Record Owner Occupied Assessor + 6 DocumentsUpdated Jul 2026

217 Harbor Dr

3 bd · 2 ba · 1,737 sqft · Garage

Last Sale Tax Bill Prior Sale Owner Records
$157,000Nov 2003 $2,1442025 1 Name on Record AssessorUpdated May 2026

220 Harbor Dr

3 bd · 2 ba · 1,513 sqft · 0.275 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$88,000Nov 1998 $5,0842025 2 Names on Record Owner Occupied AssessorUpdated May 2026

221 Harbor Dr

4 bd · 2 ba · 2,029 sqft · 0.229 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$322,000Apr 2007 $2,5702025 Amount on Record Aug 2004 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

224 Harbor Dr

3 bd · 2 ba · 1,978 sqft · 0.268 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,9642025 1 Name on Record Owner Occupied AssessorUpdated May 2026

225 Harbor Dr

3 bd · 2 ba · 1,780 sqft · 0.229 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,1292025 2 Names on Record Owner Occupied AssessorUpdated May 2026

229 Harbor Dr

3 bd · 2 ba · 1,759 sqft · 0.229 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$123,000Jul 1999 $1,9862025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

231 Harbor Dr

0.88 acres

Last Sale Tax Bill Prior Sale Owner Records
$12025 1 Name on Record AssessorUpdated May 2026

233 Harbor Dr

4 bd · 3 ba · 2,425 sqft · 0.475 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$520,000Dec 2019 $7,0412025 —Dec 2002 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

236 Harbor Dr

3 bd · 2 ba · 1,815 sqft · 0.262 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$260,500Jun 2008 $2,6092025 Amount on Record Feb 2007 2 Names on Record AssessorUpdated May 2026

237 Harbor Dr

3 bd · 2 ba · 2,051 sqft · 0.44 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$480,000Jul 2020 $7,4092025 Amount on Record Nov 1999 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

240 Harbor Dr

3 bd · 2 ba · 2,236 sqft · 0.257 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,6012025 2 Names on Record Owner Occupied AssessorUpdated May 2026

241 Harbor Dr

4 bd · 3 ba · 2,917 sqft · 0.433 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$990,900Mar 2024 $12,9182025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

244 Harbor Dr

3 bd · 2 ba · 1,794 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$96,000Oct 1995 $1,8912025 2 Names on Record Owner Occupied AssessorUpdated May 2026

245 Harbor Dr

3 bd · 2 ba · 2,542 sqft · 0.438 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$496,900Nov 2019 $7,2812025 Amount on Record Apr 1999 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

248 Harbor Dr

4 bd · 3 ba · 2,006 sqft · 0.24 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$290,000Jul 2017 $3,0602025 Amount on Record Jun 2007 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

249 Harbor Dr

4 bd · 3 ba · 2,612 sqft · 0.713 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,8922025 1 Name on Record Owner Occupied AssessorUpdated May 2026

252 Harbor Dr

3 bd · 2 ba · 1,645 sqft · 0.294 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$100Oct 2016 $5,7322025 Amount on Record Jun 2013 1 Name on Record Assessor + 2 DocumentsUpdated May 2026

256 Harbor Dr

3 bd · 2 ba · 2,057 sqft · 0.309 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$399,000Aug 2020 $5,2212025 Amount on Record Jan 2020 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

Wildfire Risk on Harbor Dr

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskLow
this street's cells rank above 24% of the US · above 7% of Florida
Wildfire LikelihoodAbout 1 in 5,000 per year
ExposureDirect
1 of 3 cells directly exposed · 2 adjoin burnable vegetation

Property Records in Nearby Streets