Orange County property records for 44 addresses on Kentucky Ave, Winter Park, FL · Last verified October 2026
| Properties | 44 |
|---|---|
| Median Sale Price | $1,400,000 |
| Deeds and Mortgages on File | 21 |
| Median Price per Sqft | $1,110 |
| Median Annual Tax Bill | $2,822 |
| Median Year Built | 1950 |
| Median Ownership Tenure | 21 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
9,542 sqft · built 1970 · 0.482 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $15,9692025 | Owner on Record | AssessorUpdated May 2026 |
3,068 sqft · built 1948 · 0.321 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $7,3852025 | Owner on Record | AssessorUpdated May 2026 |
2,296 sqft · built 1984 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $425,000Aug 2018 | $7,5452025 | 2 Owners on Record | Assessor + 1 DocumentUpdated May 2026 |
9,016 sqft · built 1986 · 0.482 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $17,4792025 | Owner on Record | AssessorUpdated May 2026 |
2,392 sqft · built 1991 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $455,000Oct 2024 | $6,5662025 | Amount on Record Dec 2000 | Owner on Record | AssessorUpdated Oct 2026 |
3 bd · 7,502 sqft · built 1946 · 0.322 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,750,000Jun 2026 | $29,4822025 | Amount on Record May 2023 | Owner on Record | Assessor + 2 DocumentsUpdated Oct 2026 |
1 bd · 1 ba · 510 sqft · built 1953 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,300,000Feb 2025 | $2,8222025 | Amount on Record Jan 2004 | Owner on Record | AssessorUpdated May 2026 |
2 bd · 2 ba · 840 sqft · built 1957 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,8292025 | Owner on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 1 ba · 1,709 sqft · built 1940 · 0.484 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,700,000Aug 2024 | $9,3652025 | Owner on Record | AssessorUpdated May 2026 |
2 bd · 1 ba · 931 sqft · built 1957 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,8222025 | Owner on Record | AssessorUpdated May 2026 |
2 bd · 1 ba · 731 sqft · built 1952 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,8222025 | Owner on Record | AssessorUpdated May 2026 |
1,098 sqft · built 1929 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $189,000Mar 2014 | $3,6412025 | Owner on Record | AssessorUpdated Sep 2026 |
4 bd · 2 ba · 2,578 sqft · built 1980 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,7512025 | 2 Owners on Record | Assessor + 1 DocumentUpdated Jun 2026 |
2,800 sqft · built 1995 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $36,500Jun 1993 | $5,8192025 | 2 Owners on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 1 ba · 1,075 sqft · built 1928 · 0.322 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,200,000Sep 2023 | $3,3472025 | —Jun 1995 | 2 Owners on Record | Assessor + 1 DocumentUpdated Sep 2026 |
1,283 sqft · built 1930 · 0.482 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $296,500Apr 2004 | $8,9282025 | Amount on Record Oct 2001 | 2 Owners on Record | AssessorUpdated May 2026 |
1,800 sqft · built 1981 · 0.161 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,000,000Nov 2004 | $6,1722025 | 2 Owners on Record | AssessorUpdated Oct 2026 |
0.161 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,000,000Nov 2004 | $3,6902025 | 2 Owners on Record | AssessorUpdated Oct 2026 |
11,470 sqft · built 1955 · 0.576 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $13,7042025 | Owner on Record | AssessorUpdated May 2026 |
3,479 sqft · built 1960 · 0.179 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,400,000May 2022 | $9,8072025 | Owner on Record | Assessor + 3 DocumentsUpdated Aug 2026 |
2 bd · 1.5 ba · 1,261 sqft · built 1951 · 0.192 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,400,000May 2022 | $2,3972025 | Owner on Record | Assessor + 2 DocumentsUpdated Aug 2026 |
0.321 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,400,000May 2022 | $1,9972025 | Owner on Record | Assessor + 1 DocumentUpdated May 2026 |
2 bd · 1 ba · 1,361 sqft · built 1952 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,400,000May 2022 | $2,3262025 | Amount on Record Oct 1995 | Owner on Record | Assessor + 1 DocumentUpdated May 2026 |
2 bd · 1 ba · 1,084 sqft · built 1950 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $85,000Feb 2010 | $2,7612025 | 2 Owners on Record | AssessorUpdated May 2026 |
2 bd · 1 ba · 714 sqft · built 1947 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $110,000Jun 2012 | $3,5292025 | Amount on Record Mar 2004 | Owner on Record | AssessorUpdated Oct 2026 |
2 bd · 1 ba · 750 sqft · built 1947 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $70,000Nov 2002 | $2,4242025 | Amount on Record Sep 1998 | Owner on Record | Assessor + 1 DocumentUpdated Sep 2026 |
2 bd · 1 ba · 1,051 sqft · built 1947 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $50,000Oct 1993 | $1,3312025 | Owner on Record | AssessorUpdated May 2026 |
2 bd · 1 ba · 922 sqft · built 1949 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $92,100May 2005 | $2,5862025 | Amount on Record Feb 2004 | Owner on Record | Assessor + 1 DocumentUpdated Sep 2026 |
2 bd · 1 ba · 810 sqft · built 1946 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $64,000May 2002 | $2,4082025 | —Dec 2001 | 2 Owners on Record | AssessorUpdated Oct 2026 |
2 bd · 1 ba · 1,069 sqft · built 1945 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $130,000Mar 2010 | $3,9282025 | Owner on Record | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 2 ba · 1,574 sqft · built 1959 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $155,000Mar 2010 | $5,5302025 | Owner on Record | Assessor + 1 DocumentUpdated May 2026 |
2 bd · 1 ba · 780 sqft · built 1945 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $150,000Aug 2007 | $1,7312025 | Amount on Record Aug 2003 | Owner on Record | AssessorUpdated May 2026 |
2 bd · 1 ba · 1,058 sqft · built 1944 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $47,500Mar 1998 | $1,2282025 | Amount on Record Jan 1996 | Owner on Record | AssessorUpdated Oct 2026 |
3 bd · 1 ba · 969 sqft · built 1950 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $92,100May 2005 | $1,7312025 | Amount on Record Jan 2004 | Owner on Record | Assessor + 1 DocumentUpdated Sep 2026 |
3 bd · 1 ba · 876 sqft · built 1954 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $90,000Feb 2000 | $1,2282025 | Owner on Record | AssessorUpdated May 2026 |
0.132 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $92,100May 2005 | $1,3312025 | Amount on Record Jan 2004 | Owner on Record | Assessor + 1 DocumentUpdated Sep 2026 |
2 bd · 1 ba · 1,413 sqft · built 1950 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $63,000Sep 1998 | $1,2282025 | Owner on Record | AssessorUpdated Sep 2026 |
4 bd · 2 ba · 1,581 sqft · built 1959 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $100,000Feb 2000 | $2,9122025 | Owner on Record | AssessorUpdated May 2026 |
1 bd · 1 ba · 584 sqft · built 1952 · 0.074 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $48,000May 2000 | $4682025 | Owner on Record | Assessor + 1 DocumentUpdated Sep 2026 |
2 bd · 1 ba · 1,096 sqft · built 1946 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $49,000May 1998 | $1,2282025 | Owner on Record | AssessorUpdated Sep 2026 |
3 bd · 2 ba · 974 sqft · built 1945 · 0.12 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $70,000Mar 2004 | Amount on Record Dec 1993 | Owner on Record | AssessorUpdated May 2026 |
4 bd · 1 ba · 1,150 sqft · built 1946 · 0.159 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,2592025 | Owner on Record | AssessorUpdated May 2026 |
0.039 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| Owner on Record | AssessorUpdated May 2026 |
0.12 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3802025 | Owner on Record | AssessorUpdated May 2026 |