Orange County property records for 44 addresses on Brookshire Ave, Winter Park, FL · Last verified October 2026
| Properties | 44 |
|---|---|
| Median Sale Price | $505,000 |
| Deeds and Mortgages on File | 60 |
| Median Price per Sqft | $369 |
| Owner Occupied | 70% |
| Median Annual Tax Bill | $3,608 |
| Median Year Built | 1959 |
| Median Ownership Tenure | 9 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
4 bd · 2 ba · 1,741 sqft · built 1960 · 0.213 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $7,1362025 | Owner on Record | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,811 sqft · built 1959 · 0.212 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $246,000Jun 2013 | $8,2192025 | Amount on Record Sep 2012 | Owner on Record | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3.5 ba · 2,244 sqft · built 1959 · 0.212 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $875,000Dec 2022 | $13,3292025 | Amount on Record Apr 2017 | 2 Owners on Record | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 1.5 ba · 1,069 sqft · built 1959 · 0.212 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $302,900Mar 2020 | $1,4962025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Jul 2026 |
3 bd · 2 ba · 1,591 sqft · built 1959 · 0.273 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $51,500Jun 2003 | $2,2652025 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 2 ba · 1,275 sqft · built 1961 · 0.212 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $225,000May 2014 | $3,2652025 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,464 sqft · built 1958 · 0.226 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $600,000Aug 2025 | $6,0802025 | Amount on Record Jun 2022 | Owner on Record | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 1.5 ba · 1,357 sqft · built 1959 · 0.212 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $160,000Mar 2015 | $3,6492025 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
3 bd · 2 ba · 1,144 sqft · built 1959 · 0.226 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $112,000Oct 1997 | $1,8302025 | Amount on Record Nov 1993 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Jun 2026 |
3 bd · 1.5 ba · 1,069 sqft · built 1959 · 0.212 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,5742025 | 2 Owners on Record | Assessor + 1 DocumentUpdated Aug 2026 |
3 bd · 2 ba · 1,144 sqft · built 1958 · 0.226 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $157,500Feb 2009 | $1,8082025 | Amount on Record Sep 2002 | Owner on Record | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,604 sqft · built 1963 · 0.212 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $250,000Jun 2016 | $4,0872025 | Amount on Record Jul 2004 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,548 sqft · built 1958 · 0.212 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $94,900Mar 1994 | $2,8422025 | Owner on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,164 sqft · built 1958 · 0.226 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $107,200May 2000 | $1,4232025 | Amount on Record Oct 1995 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jul 2026 |
3 bd · 2 ba · 1,180 sqft · built 1958 · 0.212 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $284,900Oct 2017 | $3,4232025 | Amount on Record Apr 2010 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Sep 2026 |
3 bd · 2 ba · 1,144 sqft · built 1958 · 0.226 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $260,000Jul 2017 | $3,8502025 | Amount on Record Feb 2015 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,144 sqft · built 1958 · 0.212 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $25,000Oct 1997 | $1,5682025 | 2 Owners on Record Owner Occupied | AssessorUpdated Oct 2026 |
4 bd · 4 ba · 2,565 sqft · built 1958 · 0.226 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $580,000Apr 2019 | $9,1672025 | Amount on Record Aug 2018 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
4 bd · 3 ba · 2,013 sqft · built 1958 · 0.226 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,5082025 | Owner on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 2,232 sqft · built 1958 · 0.212 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $370,500Jun 2016 | $6,6892025 | 2 Owners on Record Owner Occupied | AssessorUpdated Oct 2026 |
3 bd · 2 ba · 1,289 sqft · built 1958 · 0.226 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $455,000Jan 2022 | $8,2032025 | —Apr 2020 | 2 Owners on Record | Assessor + 6 DocumentsUpdated Oct 2026 |
4 bd · 4.75 ba · 3,707 sqft · built 2023 · 0.212 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $350,000Dec 2021 | $14,1962025 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Aug 2026 |
3 bd · 2 ba · 1,008 sqft · built 1959 · 0.273 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,7852025 | 2 Owners on Record Owner Occupied | AssessorUpdated Oct 2026 |
3 bd · 2 ba · 1,188 sqft · built 1958 · 0.262 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $21,500Jan 1996 | $1,8102025 | Owner on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 1.5 ba · 1,090 sqft · built 1959 · 0.22 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $122,900Jul 2012 | $6,0462025 | Amount on Record Jul 1999 | Owner on Record | AssessorUpdated Aug 2026 |
3 bd · 1.5 ba · 1,227 sqft · built 1959 · 0.211 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $268,000Jul 2016 | $3,6082025 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,890 sqft · built 1959 · 0.199 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $499,900Jul 2020 | $7,0292025 | Amount on Record Oct 2018 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Sep 2026 |
4 bd · 4.5 ba · 2,980 sqft · built 2018 · 0.204 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,100,000Dec 2022 | $16,0822025 | Amount on Record Dec 2019 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 1.5 ba · 1,050 sqft · built 1959 · 0.199 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $9132025 | Owner on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 1.5 ba · 1,012 sqft · built 1959 · 0.204 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,350,500Jul 2026 | $10,4672025 | Amount on Record Jan 2020 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 1.5 ba · 1,050 sqft · built 1959 · 0.199 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $490,000May 2025 | $1,9362025 | Amount on Record Feb 2005 | Owner on Record | AssessorUpdated Oct 2026 |
3 bd · 1.5 ba · 1,012 sqft · built 1959 · 0.204 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,8482025 | 2 Owners on Record | AssessorUpdated Jul 2026 |
2 bd · 1.5 ba · 1,330 sqft · built 1959 · 0.199 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $142,200May 2002 | $2,2102025 | Amount on Record Jan 2002 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,246 sqft · built 1959 · 0.204 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $589,900Mar 2026 | $6,9252025 | Amount on Record Apr 2025 | 2 Owners on Record Owner Occupied | Assessor + 6 DocumentsUpdated Oct 2026 |
3 bd · 2 ba · 1,468 sqft · built 1959 · 0.199 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Jul 2002 | $2,0772025 | Amount on Record Mar 2002 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3.5 ba · 1,841 sqft · built 1959 · 0.204 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $275,000Mar 2016 | $3542025 | —Nov 2007 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |
8 bd · 6.25 ba · 5,822 sqft · built 2018 · 0.199 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $808,000Jul 2018 | $12,2662025 | Amount on Record Dec 2016 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Sep 2026 |
8 bd · 7.25 ba · 6,110 sqft · built 2018 · 0.204 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,275,000Jul 2025 | $12,1092025 | Amount on Record Feb 2019 | Owner on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 1.5 ba · 966 sqft · built 1959 · 0.199 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2372025 | 2 Owners on Record | AssessorUpdated May 2026 |
3 bd · 1.5 ba · 1,237 sqft · built 1959 · 0.204 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $530,000Sep 2026 | $1,5002025 | Owner on Record | Assessor + 2 DocumentsUpdated Oct 2026 |
3 bd · 1.5 ba · 1,000 sqft · built 1959 · 0.2 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $505,000Jul 2025 | $6,2612025 | Amount on Record Jun 2017 | Owner on Record | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 1 ba · 1,519 sqft · built 1959 · 0.241 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,1302025 | Owner on Record Owner Occupied | AssessorUpdated May 2026 |
8 bd · 5.25 ba · 5,236 sqft · built 2008 · 0.199 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $522,000Dec 2017 | $8,0692025 | Amount on Record Aug 2005 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,516 sqft · built 1961 · 0.273 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,1932025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |