Orange County property records for 22 addresses on Penn Pl, Winter Park, FL · Last verified July 2026
| Properties | 22 |
|---|---|
| Median Sale Price | $1,335,000 |
| Deeds and Mortgages on File | 24 |
| Median Price per Sqft | $452 |
| Owner Occupied | 73% |
| Median Annual Tax Bill | $14,416 |
| Median Year Built | 2002 |
| Median Ownership Tenure | 11 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
4 bd · 3.5 ba · 3,074 sqft · 0.254 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $580,000Mar 2010 | $13,5412025 | Amount on Record Feb 2005 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 4 ba · 2,880 sqft · 0.242 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $740,900Mar 2003 | $10,6602025 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2.5 ba · 3,382 sqft · 0.257 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,500,000Nov 2020 | $23,4822025 | Amount on Record Sep 2019 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 3.5 ba · 2,950 sqft · 0.233 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,335,000Jun 2022 | $16,4582025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3.5 ba · 4,606 sqft · 0.353 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,450,000Nov 2023 | $33,6192025 | Amount on Record Aug 2010 | 1 Name on Record | Assessor + 1 DocumentUpdated May 2026 |
0.203 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $862025 | 1 Name on Record | AssessorUpdated May 2026 |
3 bd · 3.5 ba · 2,550 sqft · 0.211 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $825,000Oct 2022 | $12,6232025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Jun 2026 |
3 bd · 3.5 ba · 3,181 sqft · 0.251 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $230,000Jun 2000 | $12,4452025 | 1 Name on Record | AssessorUpdated May 2026 |
4 bd · 3.5 ba · 3,141 sqft · 0.255 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,200,000Dec 2021 | $19,0602025 | Amount on Record Apr 2015 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jul 2026 |
3 bd · 2.5 ba · 2,826 sqft · 0.237 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,233,000Oct 2021 | $13,3192025 | Amount on Record Jun 1999 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3.5 ba · 3,784 sqft · 0.389 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,325,000May 2025 | $15,8372025 | Amount on Record Jun 2004 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3 ba · 3,907 sqft · 0.452 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,075,000Oct 2022 | $24,6982025 | Amount on Record Mar 2021 | 1 Name on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
3 bd · 4.5 ba · 4,512 sqft · 0.387 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,425,000Apr 2011 | $35,8642025 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2.5 ba · 2,513 sqft · 0.209 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $400,000Aug 2009 | $10,9852025 | Amount on Record May 2008 | 1 Name on Record | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 2 ba · 3,845 sqft · 0.292 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,377,500Dec 2006 | $14,6112025 | Amount on Record Sep 2004 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2.5 ba · 2,311 sqft · 0.199 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,100,000Aug 2022 | $16,3292025 | Amount on Record Jun 2017 | 1 Name on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
3 bd · 3.5 ba · 3,354 sqft · 0.289 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,202,000Oct 2018 | $8,1122025 | Amount on Record May 2010 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 3.5 ba · 2,540 sqft · 0.199 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $675,000Feb 2005 | $10,0432025 | Amount on Record Jan 2001 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3 ba · 3,797 sqft · 0.29 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,015,000Apr 2005 | $13,8912025 | Amount on Record Aug 2003 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 3 ba · 2,482 sqft · 0.199 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $697,900Feb 2005 | $10,3442025 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 4 ba · 3,721 sqft · 0.289 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $804,000Oct 2000 | $14,4162025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 4 ba · 3,209 sqft · 0.282 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,000,000Mar 2015 | $24,8692025 | Amount on Record Apr 2004 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Jul 2026 |
Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020
| Wildfire Risk | Not rated no burnable land in reach |
|---|---|
| Wildfire Likelihood | Negligible |
| Exposure | None beyond ember reach |