Painted Leaf Dr, Winter Garden, FL Property Records

Orange County property records for 11 addresses on Painted Leaf Dr, Winter Garden, FL · Last verified June 2026

Painted Leaf Dr Highlights

Properties 11
Median Sale Price $474,700
Deeds and Mortgages on File 26
Median Price per Sqft $190
Owner Occupied 91%
Median Annual Tax Bill $7,593
Median Year Built 2021
Median Ownership Tenure 5 years

Properties on Painted Leaf Dr

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

5959 Painted Leaf Dr

3 bd · 2.5 ba · 1,743 sqft · 0.113 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,379Nov 2020 $4,6932025 Amount on Record Jul 2020 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5965 Painted Leaf Dr

3 bd · 2.5 ba · 1,967 sqft · 0.095 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,535Jan 2021 $6,8892025 Amount on Record Sep 2020 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

5970 Painted Leaf Dr

5 bd · 4.5 ba · 3,119 sqft · 0.137 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$474,700Jan 2020 $6,3432025 Amount on Record Aug 2019 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5971 Painted Leaf Dr

3 bd · 2.5 ba · 1,967 sqft · 0.095 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$375,600Dec 2020 $7,8682025 Amount on Record Jul 2020 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5976 Painted Leaf Dr

5 bd · 4.5 ba · 3,086 sqft · 0.137 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$539,100Oct 2021 $8,5612025 Amount on Record May 2021 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5977 Painted Leaf Dr

3 bd · 2.5 ba · 1,967 sqft · 0.095 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$546,100Nov 2023 $8,6592025 1 Name on Record Assessor + 4 DocumentsUpdated May 2026

5983 Painted Leaf Dr

4 bd · 2.5 ba · 1,967 sqft · 0.095 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$390,500Jul 2021 $6,2522025 Amount on Record Dec 2020 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

5988 Painted Leaf Dr

5 bd · 4.5 ba · 3,062 sqft · 0.137 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$521,500Sep 2021 $11,2462025 Amount on Record Apr 2021 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

5989 Painted Leaf Dr

3 bd · 2.5 ba · 1,733 sqft · 0.095 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$499,000Apr 2025 $7,7682025 Amount on Record Aug 2021 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5994 Painted Leaf Dr

5 bd · 4.5 ba · 3,119 sqft · 0.152 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$752,500Mar 2025 $7,5932025 Amount on Record May 2021 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5995 Painted Leaf Dr

3 bd · 2.5 ba · 1,967 sqft · 0.113 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$375,000Aug 2021 $6,9212025 Amount on Record Mar 2021 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

Wildfire Risk on Painted Leaf Dr

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

Wildfire RiskModerate
this street's cells rank at the 54th percentile of exposed land nationally · 25th in Florida
Wildfire LikelihoodModerate — about 1 in 658 per year
ExposureDirect
1 of 1 cells directly exposed · 1 adjoin burnable vegetation

Property Records in Nearby Streets