Orange County property records for 18 addresses on Fifeshire Dr, Winter Park, FL · Last verified August 2026
| Properties | 18 |
|---|---|
| Median Sale Price | $390,000 |
| Deeds and Mortgages on File | 22 |
| Median Price per Sqft | $201 |
| Owner Occupied | 72% |
| Median Annual Tax Bill | $4,749 |
| Median Year Built | 1961 |
| Median Ownership Tenure | 11 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
4 bd · 2 ba · 1,684 sqft · 0.238 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $100Mar 2024 | $3,3762025 | Amount on Record Aug 2003 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated Aug 2026 |
3 bd · 2 ba · 1,608 sqft · 0.238 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,0802025 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,857 sqft · 0.201 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $260,000Mar 2015 | $4,4742025 | Amount on Record Jul 2012 | 2 Names on Record Owner Occupied | Assessor + 4 DocumentsUpdated Jul 2026 |
4 bd · 2 ba · 1,652 sqft · 0.201 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $308,150Oct 2014 | $4,8172025 | Amount on Record May 2014 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,373 sqft · 0.189 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $200,000Dec 2006 | $6,7202025 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 2 ba · 1,624 sqft · 0.189 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $415,000Sep 2020 | $8,0312025 | Amount on Record Oct 2019 | 2 Names on Record Owner Occupied | Assessor + 4 DocumentsUpdated May 2026 |
3 bd · 2 ba · 2,087 sqft · 0.189 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,7272025 | 2 Names on Record | AssessorUpdated May 2026 |
5 bd · 4 ba · 2,317 sqft · 0.189 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $180,000Jan 2002 | $3,4362025 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,390 sqft · 0.176 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Aug 2016 | $2,3042025 | Amount on Record Aug 2016 | 2 Names on Record | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,283 sqft · 0.176 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $105,300Jun 1998 | $1,8582025 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,313 sqft · 0.176 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $96,500Oct 1995 | $7,0332025 | 1 Name on Record | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,420 sqft · 0.176 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $390,000Mar 2022 | $8,4292025 | Amount on Record Aug 2017 | 1 Name on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,770 sqft · 0.176 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $180,000Jun 2004 | $2,9942025 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 2.5 ba · 1,940 sqft · 0.176 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $349,000Mar 2015 | $4,6402025 | Amount on Record Feb 2005 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,906 sqft · 0.189 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $7,4732025 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2 ba · 2,108 sqft · 0.189 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $353,700Dec 2017 | $4,7492025 | Amount on Record Feb 2015 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
5 bd · 3 ba · 2,212 sqft · 0.213 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $720,000Jan 2024 | $8,0972025 | Amount on Record Sep 2022 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated Jun 2026 |
4 bd · 2.5 ba · 2,406 sqft · 0.213 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $485,000Jul 2019 | $5,3502025 | Amount on Record Dec 2000 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020
| Wildfire Risk | Low this street's cells rank at the 2nd percentile of exposed land nationally · 3rd in Florida |
|---|---|
| Wildfire Likelihood | Low — less than 1 in 10,000 per year |
| Exposure | Direct 1 of 3 cells directly exposed · 3 adjoin burnable vegetation |