Stirling Ave, Winter Park, FL Property Records

Orange County property records for 15 addresses on Stirling Ave, Winter Park, FL · Last verified May 2026

Stirling Ave Highlights

Properties 15
Median Sale Price $1,280,000
Deeds and Mortgages on File 15
Median Price per Sqft $312
Owner Occupied 80%
Median Annual Tax Bill $17,514
Median Year Built 1987
Median Ownership Tenure 12 years

Properties on Stirling Ave

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

100 Stirling Ave

8 bd · 8.25 ba · 7,850 sqft · built 2011 · 0.322 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,150,000Jul 2022 $20,4272025 Amount on Record Oct 2010 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

144 Stirling Ave

3 bd · 3 ba · 2,042 sqft · built 1925 · 0.371 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,0802025 1 Name on Record Owner Occupied AssessorUpdated May 2026

151 Stirling Ave

3 bd · 2 ba · 2,232 sqft · built 1960 · 0.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$925,000May 2024 $13,0072025 —Mar 2022 2 Names on Record Owner Occupied AssessorUpdated May 2026

210 Stirling Ave

5 bd · 3.5 ba · 3,335 sqft · built 1925 · 0.482 acres

Last Sale Tax Bill Prior Sale Owner Records
$635,000Jul 2010 $12,0842025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

211 Stirling Ave

4 bd · 4.5 ba · 3,032 sqft · built 1998 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$325,000Sep 1997 $19,9642025 1 Name on Record Owner Occupied AssessorUpdated May 2026

230 Stirling Ave

5 bd · 5.5 ba · 3,924 sqft · built 2000 · 0.484 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,225,000Jul 2017 $17,5142025 Amount on Record Jun 2006 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

235 Stirling Ave

6 bd · 4.5 ba · 3,288 sqft · built 1986 · 0.37 acres

Last Sale Tax Bill Prior Sale Owner Records
$14,3382025 2 Names on Record Assessor + 1 DocumentUpdated May 2026

250 Stirling Ave

5 bd · 4.5 ba · 4,580 sqft · built 1993 · 0.691 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,280,000Mar 2012 $21,7632025 Amount on Record Nov 2001 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

255 Stirling Ave

4 bd · 3.5 ba · 3,364 sqft · built 1982 · 0.317 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,835,000Nov 2025 $32,3312025 Amount on Record May 2023 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

275 Stirling Ave

3 bd · 2.5 ba · 2,833 sqft · built 1977 · 0.567 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,080,000May 2021 $45,5542025 Amount on Record Aug 2019 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

280 Stirling Ave

3 bd · 2.5 ba · 3,190 sqft · built 1992 · 0.559 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,9982025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

290 Stirling Ave

0.562 acres

Last Sale Tax Bill Prior Sale Owner Records
$2982025 1 Name on Record AssessorUpdated May 2026

300 Stirling Ave

3 bd · 3 ba · 3,170 sqft · built 1985 · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$313,300Oct 1995 $8,2152025 1 Name on Record Owner Occupied AssessorUpdated May 2026

320 Stirling Ave

3 bd · 3 ba · 2,940 sqft · built 1987 · 0.614 acres

Last Sale Tax Bill Prior Sale Owner Records
$485,000Jan 1998 $20,5852025 1 Name on Record AssessorUpdated May 2026

321 Stirling Ave

10 bd · 11.25 ba · 8,840 sqft · built 2017 · 0.32 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jul 2014 $28,2162025 Amount on Record Aug 1998 2 Names on Record Owner Occupied AssessorUpdated May 2026

Wildfire Risk on Stirling Ave

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

Wildfire RiskLow
this street's cells rank above 19% of the US · above 6% of Florida
Wildfire LikelihoodAbout 1 in 6,250 per year
ExposureDirect
2 of 3 cells directly exposed · 2 adjoin burnable vegetation

Property Records in Nearby Streets