Gary Dr, Winter Garden, FL Property Records

Orange County property records for 15 addresses on Gary Dr, Winter Garden, FL · Last verified May 2026

Gary Dr Highlights

Properties 15
Median Sale Price $261,000
Deeds and Mortgages on File 12
Median Price per Sqft $227
Owner Occupied 53%
Median Annual Tax Bill $4,415
Median Year Built 1959
Median Ownership Tenure 7 years

Properties on Gary Dr

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

201 Gary Dr

4 bd · 1.5 ba · 2,519 sqft · 0.244 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$45,300Feb 2022 $3,1372025 Amount on Record Aug 2014 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

212 Gary Dr

2 bd · 1 ba · 1,226 sqft · 0.237 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$63,500Feb 2019 $8092025 Amount on Record Nov 1998 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

213 Gary Dr

4 bd · 3 ba · 1,724 sqft · 0.237 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,1032025 2 Names on Record Owner Occupied AssessorUpdated May 2026

225 Gary Dr

3 bd · 2 ba · 2,037 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$385,000Jun 2020 $5,9872025 Amount on Record Apr 2014 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

230 Gary Dr

3 bd · 2 ba · 1,616 sqft · 0.238 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$250,000Apr 2006 $1,8632025 2 Names on Record Owner Occupied AssessorUpdated May 2026

236 Gary Dr

3 bd · 2 ba · 1,093 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$261,000Apr 2019 Amount on Record Oct 2013 2 Names on Record Assessor + 2 DocumentsUpdated May 2026

237 Gary Dr

2 bd · 1 ba · 984 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$247,000Jul 2018 $3,1882025 Amount on Record Jun 2015 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

254 Gary Dr

5 bd · 4 ba · 2,742 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$76,000Sep 2013 $4,8402025 Amount on Record May 2013 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

255 Gary Dr

3 bd · 2 ba · 1,260 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$78,000Jul 1999 $4,4152025 1 Name on Record AssessorUpdated May 2026

260 Gary Dr

3 bd · 1.5 ba · 1,337 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$7122025 2 Names on Record Owner Occupied AssessorUpdated May 2026

267 Gary Dr

4 bd · 2 ba · 1,827 sqft · 0.238 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$5,2372025 2 Names on Record AssessorUpdated May 2026

278 Gary Dr

0.238 acres

Last Sale Tax Bill Prior Sale Owner Records
$57,900Nov 2013 $3,0822025 2 Names on Record AssessorUpdated May 2026

279 Gary Dr

3 bd · 2 ba · 1,220 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$277,000Jun 2021 $5,7832025 2 Names on Record Assessor + 1 DocumentUpdated May 2026

290 Gary Dr

3 bd · 2 ba · 1,758 sqft · 0.246 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$452,000Jul 2024 $6,1482025 1 Name on Record AssessorUpdated May 2026

291 Gary Dr

6 bd · 7.25 ba · 5,548 sqft · 0.246 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$164,000May 2015 $5,2722025 Amount on Record Oct 2006 2 Names on Record AssessorUpdated May 2026

Wildfire Risk on Gary Dr

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

Wildfire RiskLow
this street's cells rank at the 24th percentile of exposed land nationally · 7th in Florida
Wildfire LikelihoodLow — about 1 in 3,896 per year
ExposureDirect
1 of 3 cells directly exposed · 3 adjoin burnable vegetation

Property Records in Nearby Streets