Old Bear Run, Winter Park, FL Property Records

Seminole County property records for 6 addresses on Old Bear Run, Winter Park, FL · Last verified July 2026

Old Bear Run Highlights

Properties 6
Median Sale Price $795,000
Deeds and Mortgages on File 7
Median Price per Sqft $210
Owner Occupied 100%
Median Annual Tax Bill $12,858
Median Year Built 1990
Median Ownership Tenure 11 years

Properties on Old Bear Run

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

4445 Old Bear Run

4 bd · 5 ba · 3,778 sqft · 0.711 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$795,000Mar 2012 $12,8582025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

4455 Old Bear Run

5 bd · 6 ba · 6,747 sqft · 0.709 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,350,000Sep 2020 $20,0692025 Amount on Record Dec 2019 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

4457 Old Bear Run

4 bd · 2 ba · 2,534 sqft · 0.766 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$100Jan 1976 $4,6162025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

4463 Old Bear Run

4 bd · 2 ba · 2,282 sqft · 0.817 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$715,000Mar 2022 $11,2262025 Amount on Record Oct 1997 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

4469 Old Bear Run

5 bd · 5.5 ba · 4,288 sqft · 0.739 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$754,000Jul 2015 $11,7322025 Amount on Record Jul 2014 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

4475 Old Bear Run

4 bd · 6 ba · 5,435 sqft · 0.718 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,350,000Jan 2005 $14,1662025 Amount on Record Feb 2002 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

Wildfire Risk on Old Bear Run

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

Wildfire RiskLow
this street's cells rank at the 1st percentile of exposed land nationally · 1st in Florida
Wildfire LikelihoodLow — less than 1 in 10,000 per year
ExposureDirect
1 of 1 cells directly exposed · 1 adjoin burnable vegetation

Property Records in Nearby Streets