Orange County property records for 35 addresses on Cortland Ave, Winter Park, FL · Last verified September 2026
| Properties | 35 |
|---|---|
| Median Sale Price | $1,245,000 |
| Deeds and Mortgages on File | 63 |
| Median Price per Sqft | $445 |
| Owner Occupied | 77% |
| Median Annual Tax Bill | $10,343 |
| Median Year Built | 1966 |
| Median Ownership Tenure | 7 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
3 bd · 2.5 ba · 2,994 sqft · built 1926 · 0.278 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,100,000Jul 2025 | $24,9412025 | Amount on Record Sep 2020 | 2 Owners on Record Owner Occupied | Assessor + 7 DocumentsUpdated Aug 2026 |
5 bd · 3.5 ba · 3,775 sqft · built 1926 · 0.295 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,495,000Apr 2025 | $12,3682025 | Amount on Record Aug 2013 | Owner on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 2.5 ba · 2,764 sqft · built 1935 · 0.286 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $779,000Jul 2013 | $11,0422025 | Amount on Record Sep 2001 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |
2 bd · 1.5 ba · 1,692 sqft · built 1926 · 0.286 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $8,9392025 | 2 Owners on Record | AssessorUpdated May 2026 |
4 bd · 4.5 ba · 3,523 sqft · built 2012 · 0.344 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,850,000Jun 2021 | $23,1652025 | Amount on Record Jun 2010 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,632 sqft · built 1940 · 0.344 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,245,000Sep 2025 | $4,1392025 | Owner on Record | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3 ba · 3,019 sqft · built 1925 · 0.286 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $995,100Apr 2021 | $14,5132025 | Amount on Record May 2004 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 3.5 ba · 2,891 sqft · built 1960 · 0.344 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,9732025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3 ba · 2,691 sqft · built 1992 · 0.285 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $622,500Apr 2015 | $10,0982025 | Amount on Record Aug 2012 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3.5 ba · 2,942 sqft · built 1995 · 0.33 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,425,000May 2023 | $18,5242025 | Amount on Record Jun 2012 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 3 ba · 2,568 sqft · built 1950 · 0.285 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $641,500Aug 2008 | $7,1512025 | Amount on Record Apr 2005 | 2 Owners on Record | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3 ba · 3,187 sqft · built 1940 · 0.358 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $990,000Sep 2020 | $14,9012025 | Amount on Record Feb 2017 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
8 bd · 9.25 ba · 8,986 sqft · built 2007 · 0.285 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $650,100Sep 2019 | $17,6462025 | Amount on Record Apr 2006 | 2 Owners on Record Owner Occupied | Assessor + 4 DocumentsUpdated Sep 2026 |
3 bd · 4 ba · 3,836 sqft · built 1990 · 0.465 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $610,000Sep 1995 | $12,6692025 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
10 bd · 9.25 ba · 6,072 sqft · built 2017 · 0.285 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $949,800Nov 2017 | $14,2842025 | Amount on Record Jan 2016 | 2 Owners on Record | Assessor + 5 DocumentsUpdated Sep 2026 |
4 bd · 3 ba · 2,434 sqft · built 1950 · 0.285 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $407,000Sep 2010 | $7,3062025 | Amount on Record Jun 2010 | 2 Owners on Record Owner Occupied | AssessorUpdated Sep 2026 |
3 bd · 2 ba · 2,063 sqft · built 1981 · 0.19 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $920,000Jul 2026 | $4,5382025 | Amount on Record Mar 2007 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Aug 2026 |
4 bd · 4.5 ba · 3,960 sqft · built 1946 · 0.566 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $9,2332025 | 2 Owners on Record | Assessor + 2 DocumentsUpdated May 2026 |
5 bd · 2 ba · 2,440 sqft · built 1929 · 0.328 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $68,500May 1994 | $3,8122025 | Amount on Record Sep 1993 | 2 Owners on Record Owner Occupied | AssessorUpdated Sep 2026 |
4 bd · 3.5 ba · 2,596 sqft · built 1973 · 0.223 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,1972025 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |
2 bd · 2 ba · 1,382 sqft · built 1952 · 0.229 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $750,000Sep 2025 | $7,0292025 | Amount on Record Jun 2005 | Owner on Record | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3.5 ba · 4,027 sqft · built 1940 · 0.652 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,375,000Mar 2017 | $21,3352025 | Amount on Record Jan 2005 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
2 bd · 2 ba · 1,454 sqft · built 1946 · 0.178 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $420,000Mar 2021 | $9,1602025 | Amount on Record Jun 2016 | Owner on Record | Assessor + 3 DocumentsUpdated May 2026 |
4 bd · 4 ba · 3,129 sqft · built 1992 · 0.298 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $588,400Nov 1995 | $10,5932025 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |
10 bd · 11.25 ba · 7,705 sqft · built 2016 · 0.258 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,330,000Nov 2016 | $19,1722025 | Amount on Record Oct 2016 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
8 bd · 11.25 ba · 8,228 sqft · built 2008 · 0.258 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,495,000May 2024 | $32,1822025 | Amount on Record Sep 2009 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 3 ba · 2,479 sqft · built 1973 · 0.224 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $5,7572025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
8 bd · 13.25 ba · 9,286 sqft · built 2008 · 0.345 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,600,000Aug 2013 | $24,4262025 | Amount on Record Aug 2010 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |
5 bd · 3 ba · 2,221 sqft · built 1972 · 0.224 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $545,000Jun 2019 | $9,0882025 | Amount on Record May 1999 | 2 Owners on Record Owner Occupied | Assessor + 8 DocumentsUpdated May 2026 |
10 bd · 12.75 ba · 9,304 sqft · built 2019 · 0.345 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,950,000Oct 2020 | $37,6102025 | Amount on Record Aug 2019 | 2 Owners on Record Owner Occupied | Assessor + 5 DocumentsUpdated May 2026 |
10 bd · 8.25 ba · 6,351 sqft · built 2002 · 0.224 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $315,000Aug 2001 | $10,3432025 | Amount on Record Jul 1999 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Jun 2026 |
3 bd · 1 ba · 1,317 sqft · built 1951 · 0.207 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,1202025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3 ba · 2,823 sqft · built 1996 · 0.224 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,150,000Mar 2024 | $17,9412025 | Amount on Record Jun 1994 | Owner on Record | Assessor + 3 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,767 sqft · built 1949 · 0.225 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $248,500Jun 1999 | $4,3202025 | Amount on Record Mar 1994 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |
2 bd · 2 ba · 1,854 sqft · built 1966 · 0.169 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $582,571Apr 2017 | $8,8702025 | Amount on Record Jul 2005 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jul 2026 |