Orange County property records for 48 addresses on Oglesby Ave, Winter Park, FL · Last verified October 2026
| Properties | 48 |
|---|---|
| Median Sale Price | $432,000 |
| Deeds and Mortgages on File | 41 |
| Median Price per Sqft | $381 |
| Owner Occupied | 33% |
| Median Annual Tax Bill | $2,949 |
| Median Year Built | 1951 |
| Median Ownership Tenure | 15 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
1 bd · 1 ba · 488 sqft · built 1950 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,8472025 | Owner on Record | AssessorUpdated May 2026 |
1 bd · 1 ba · 809 sqft · built 1950 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,9222025 | Owner on Record | AssessorUpdated May 2026 |
4 bd · 3 ba · 1,784 sqft · built 1951 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $110,000Mar 2014 | $3,8282025 | —Feb 2014 | Owner on Record Owner Occupied | AssessorUpdated Sep 2026 |
2 bd · 1 ba · 728 sqft · built 1951 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $164,800Aug 2018 | $3,5712025 | Owner on Record | Assessor + 4 DocumentsUpdated Sep 2026 |
3 bd · 1.5 ba · 839 sqft · built 1951 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $225,000Feb 2021 | $2,7102025 | Owner on Record Owner Occupied | Assessor + 4 DocumentsUpdated May 2026 |
1 bd · 1 ba · 899 sqft · built 1951 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $64,000Nov 2013 | $2,2852025 | Owner on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,115 sqft · built 1951 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $432,000Feb 2024 | $6,4322025 | Amount on Record May 2021 | Owner on Record | Assessor + 4 DocumentsUpdated Oct 2026 |
2 bd · 1 ba · 794 sqft · built 1954 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $126,300Jan 2017 | $4,1482025 | Amount on Record Mar 2015 | 2 Owners on Record | Assessor + 1 DocumentUpdated Sep 2026 |
2 bd · 1 ba · 884 sqft · built 1944 · 0.161 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $72,900May 2000 | $1,3732025 | 2 Owners on Record Owner Occupied | AssessorUpdated Sep 2026 |
3 bd · 2 ba · 1,100 sqft · built 1957 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Aug 2011 | $3,3742025 | Amount on Record Jan 2011 | 2 Owners on Record | AssessorUpdated Sep 2026 |
2 bd · 1 ba · 894 sqft · built 1954 · 0.161 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $341,000Mar 2022 | $4,9452025 | Amount on Record May 2000 | 2 Owners on Record Owner Occupied | Assessor + 4 DocumentsUpdated Oct 2026 |
2 bd · 1 ba · 676 sqft · built 1958 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $155,000Oct 2020 | $2,8952025 | Amount on Record May 2000 | 2 Owners on Record | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 2 ba · 1,157 sqft · built 1953 · 0.161 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Feb 2001 | $3,4852025 | Amount on Record Nov 2000 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Sep 2026 |
2 bd · 2 ba · 1,447 sqft · built 1958 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $90,000Nov 2013 | $3,4592025 | Amount on Record Nov 2010 | Owner on Record | AssessorUpdated Sep 2026 |
2 bd · 2 ba · 1,231 sqft · built 1952 · 0.161 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,2642025 | Owner on Record Owner Occupied | AssessorUpdated May 2026 |
2 bd · 1 ba · 780 sqft · built 1959 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $52,500Jun 2015 | $1,3282025 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
2 bd · 1 ba · 780 sqft · built 1951 · 0.161 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $85,000Mar 2013 | $1,2472025 | Amount on Record Oct 2003 | 2 Owners on Record Owner Occupied | AssessorUpdated Jul 2026 |
2 bd · 1 ba · 780 sqft · built 1959 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $215,000Jan 2021 | $3,6622025 | Amount on Record Apr 2017 | Owner on Record | Assessor + 2 DocumentsUpdated May 2026 |
2 bd · 1 ba · 1,424 sqft · built 1959 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Oct 2000 | $1,6892025 | Amount on Record Jan 1998 | Owner on Record | Assessor + 1 DocumentUpdated Sep 2026 |
3 bd · 2 ba · 1,158 sqft · built 1935 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $126,000Jan 2016 | $3,3402025 | Amount on Record Oct 2002 | Owner on Record | AssessorUpdated May 2026 |
4 bd · 1.5 ba · 2,676 sqft · built 1925 · 0.482 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $5792025 | Owner on Record | AssessorUpdated May 2026 |
2 bd · 1 ba · 951 sqft · built 1961 · 0.161 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,1712025 | 2 Owners on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 1 ba · 1,318 sqft · built 1948 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $100,000May 2002 | $1,1002025 | Amount on Record Jul 2001 | Owner on Record Owner Occupied | AssessorUpdated May 2026 |
7 bd · 3.5 ba · 2,971 sqft · built 1952 · 0.321 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —May 2010 | $7,2072025 | Amount on Record Oct 2002 | 2 Owners on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2 ba · 1,179 sqft · built 1969 · 0.192 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $55,000Dec 1997 | $4,1642025 | Owner on Record | AssessorUpdated Sep 2026 |
3 bd · 3 ba · 1,431 sqft · built 1925 · 0.353 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,800,000Aug 2026 | $2,9492025 | Amount on Record Dec 2003 | Owner on Record | Assessor + 1 DocumentUpdated Oct 2026 |
1 bd · 1 ba · 664 sqft · built 1946 · 0.321 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $187,000Jan 2007 | $1,7762025 | Amount on Record Jun 2000 | Owner on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 1 ba · 1,062 sqft · built 1940 · 0.321 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $200,000May 2006 | $1,7762025 | Amount on Record Aug 2000 | Owner on Record | AssessorUpdated Oct 2026 |
8 bd · 6.25 ba · 5,546 sqft · built 2011 · 0.536 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $77,000May 1994 | $5,3412025 | Owner on Record Owner Occupied | AssessorUpdated May 2026 |
2 bd · 1 ba · 834 sqft · built 1940 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $130,000Nov 2009 | $3,4932025 | Amount on Record May 2005 | 2 Owners on Record | AssessorUpdated Sep 2026 |
3 bd · 1 ba · 808 sqft · built 1939 · 0.092 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $8,000Apr 2013 | $5252025 | Amount on Record Oct 1993 | Owner on Record | AssessorUpdated May 2026 |
2 bd · 1 ba · 976 sqft · built 1949 · 0.027 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $92,100May 2005 | $4682025 | Amount on Record Dec 2002 | Owner on Record | Assessor + 1 DocumentUpdated Sep 2026 |
2 bd · 1 ba · 1,129 sqft · built 1945 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $130,000Apr 2009 | $3,8622025 | Amount on Record Nov 1995 | Owner on Record | Assessor + 1 DocumentUpdated Sep 2026 |
2 bd · 1 ba · 1,080 sqft · built 1950 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $110,000Oct 2014 | $2,9502025 | Amount on Record Jun 1994 | Owner on Record | AssessorUpdated Oct 2026 |
0.051 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,000Feb 2003 | Owner on Record | AssessorUpdated Sep 2026 |
2 bd · 1 ba · 1,045 sqft · built 1974 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $101,000May 2013 | $3,4912025 | Amount on Record Oct 1994 | Owner on Record | AssessorUpdated May 2026 |
3 bd · 2 ba · 932 sqft · built 1953 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $60,800Oct 2013 | $2,6392025 | Amount on Record Mar 2013 | Owner on Record | AssessorUpdated Sep 2026 |
2 bd · 1 ba · 775 sqft · built 1953 · 0.101 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $4,000Sep 2008 | $1252025 | Amount on Record Jul 2006 | Owner on Record | AssessorUpdated May 2026 |
2 bd · 1 ba · 951 sqft · built 1945 · 0.243 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $86,500Mar 2003 | Amount on Record Aug 2001 | Owner on Record | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,419 sqft · built 1948 · 0.393 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $98,000Aug 2002 | Amount on Record May 2001 | Owner on Record | AssessorUpdated Oct 2026 |
5 bd · 2 ba · 2,160 sqft · built 1935 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $195,000May 2005 | Amount on Record Aug 2004 | Owner on Record | AssessorUpdated Sep 2026 |
3 bd · 1 ba · 1,082 sqft · built 1952 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $62,000Jul 2011 | $1,7242025 | Amount on Record Apr 2004 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2 ba · 1,444 sqft · built 1953 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $68,500Apr 1998 | $5,1772025 | Amount on Record Jul 1997 | 2 Owners on Record | AssessorUpdated May 2026 |
2 bd · 2 ba · 1,338 sqft · built 1945 · 0.192 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $17,074Jan 2011 | $2,8672025 | —Mar 2010 | 2 Owners on Record | AssessorUpdated May 2026 |
2 bd · 2 ba · 981 sqft · built 1991 · 0.192 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $90,000Dec 2000 | $4,0432025 | Amount on Record Jun 1993 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Sep 2026 |
2 bd · 1 ba · 1,242 sqft · built 1988 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $173,900Jul 2004 | $2,4172025 | Amount on Record Mar 2004 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Sep 2026 |
5 bd · 5 ba · 5,911 sqft · built 2015 · 1.12 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,375,000Nov 2021 | $40,4082025 | Amount on Record Apr 2020 | 2 Owners on Record Owner Occupied | Assessor + 4 DocumentsUpdated May 2026 |
8 bd · 5.25 ba · 4,870 sqft · built 2019 · 0.166 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,025,000Jul 2025 | $9,6672025 | Amount on Record Dec 2021 | 2 Owners on Record Owner Occupied | Assessor + 5 DocumentsUpdated May 2026 |