Orange County property records for 22 addresses on Madeline Ave, Winter Park, FL · Last verified July 2026
| Properties | 22 |
|---|---|
| Median Sale Price | $405,000 |
| Deeds and Mortgages on File | 26 |
| Median Price per Sqft | $239 |
| Owner Occupied | 73% |
| Median Annual Tax Bill | $2,514 |
| Median Year Built | 1956 |
| Median Ownership Tenure | 10 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
3 bd · 1 ba · 1,116 sqft · built 1953 · 0.172 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $68,000Jun 1997 | $1,1632025 | Amount on Record Dec 1996 | 1 Name on Record | AssessorUpdated May 2026 |
4 bd · 3 ba · 2,266 sqft · built 1972 · 0.313 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $550,000Sep 2021 | $8,4592025 | Amount on Record Aug 2014 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
8 bd · 7.25 ba · 4,824 sqft · built 2013 · 0.192 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $492,000Oct 2018 | $7,3572025 | Amount on Record Aug 2016 | 1 Name on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,160 sqft · built 1956 · 0.201 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $50,000May 1998 | $2,5142025 | Amount on Record Aug 1997 | 1 Name on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
2 bd · 1 ba · 1,151 sqft · built 1954 · 0.192 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,1982025 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 1 ba · 1,252 sqft · built 1954 · 0.193 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $300,000Jan 2026 | $1,0232025 | 1 Name on Record | Assessor + 1 DocumentUpdated May 2026 |
2 bd · 1 ba · 959 sqft · built 1952 · 0.193 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $850,000Dec 2025 | $8,2652025 | Amount on Record Feb 2023 | 2 Names on Record Owner Occupied | Assessor + 4 DocumentsUpdated Jul 2026 |
2 bd · 1 ba · 905 sqft · built 1952 · 0.193 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $145,000Oct 2016 | $1,9342025 | Amount on Record Sep 2000 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 1.5 ba · 1,232 sqft · built 1971 · 0.202 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,9252025 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 1 ba · 1,168 sqft · built 1954 · 0.193 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $103,500Mar 2000 | $9642025 | Amount on Record Jun 1993 | 1 Name on Record | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,420 sqft · built 1972 · 0.193 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $24,000Aug 2000 | $5,2782025 | 2 Names on Record | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,244 sqft · built 1972 · 0.202 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $180,000Apr 2014 | $2,3662025 | Amount on Record Sep 2013 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,170 sqft · built 1954 · 0.193 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $405,000Dec 2024 | $5,6402025 | Amount on Record Jul 2000 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 4 ba · 2,882 sqft · built 2007 · 0.193 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $370,000Jul 2013 | $8,1102025 | Amount on Record Dec 2011 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 3 ba · 2,713 sqft · built 1953 · 0.193 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $112,000Aug 2013 | $3,8962025 | Amount on Record Aug 2013 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,243 sqft · built 1954 · 0.193 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,0532025 | 2 Names on Record Owner Occupied | AssessorUpdated Jul 2026 |
4 bd · 1 ba · 1,473 sqft · built 1959 · 0.193 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,1742025 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,298 sqft · built 1971 · 0.193 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $132,700Apr 2002 | $1,6362025 | Amount on Record Nov 1998 | 1 Name on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
5 bd · 2 ba · 1,733 sqft · built 1971 · 0.193 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $36,400Oct 2018 | $2,1912025 | 2 Names on Record Owner Occupied | Assessor + 6 DocumentsUpdated May 2026 |
4 bd · 3.5 ba · 1,864 sqft · built 1971 · 0.193 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $255,000Jul 2017 | $3,8902025 | Amount on Record May 1995 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
2 bd · 2 ba · 1,223 sqft · built 1956 · 0.198 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $100Dec 1995 | $6982025 | 1 Name on Record | AssessorUpdated May 2026 |
3 bd · 1.5 ba · 1,091 sqft · built 1956 · 0.193 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $100Mar 2017 | $5,9012025 | Amount on Record Oct 2016 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |