Orange County property records for 68 addresses on S Main St, Winter Garden, FL · Last verified August 2026
| Properties | 68 |
|---|---|
| Median Sale Price | $625,000 |
| Deeds and Mortgages on File | 69 |
| Median Price per Sqft | $319 |
| Owner Occupied | 25% |
| Median Annual Tax Bill | $4,761 |
| Median Year Built | 1953 |
| Median Ownership Tenure | 7 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
1,560 sqft · built 1925 · 0.049 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $435,000Jul 2022 | $1,9222025 | Amount on Record — | 1 Name on Record | Assessor + 2 DocumentsUpdated May 2026 |
0.239 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $28,200Jun 1995 | $12025 | 1 Name on Record | AssessorUpdated May 2026 |
3,072 sqft · built 1912 · 0.072 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $4,000,000Jan 2026 | $6,2332025 | 1 Name on Record | Assessor + 1 DocumentUpdated May 2026 |
1 bd · 1 ba · 9,145 sqft · built 1916 · 0.146 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $11,5482025 | 1 Name on Record | AssessorUpdated May 2026 |
4,240 sqft · built 1912 · 0.092 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $9,4642025 | 1 Name on Record | AssessorUpdated May 2026 |
3,131 sqft · built 1912 · 0.07 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,000,000Jul 2024 | $14,5402025 | 1 Name on Record | AssessorUpdated May 2026 |
1,022 sqft · built 1940 · 0.032 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $25,000Aug 1998 | $1,9452025 | 1 Name on Record | AssessorUpdated May 2026 |
4,350 sqft · built 1955 · 0.064 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,000,000Sep 2020 | $18,8002025 | Amount on Record Dec 2000 | 1 Name on Record | Assessor + 1 DocumentUpdated Aug 2026 |
1,900 sqft · built 1922 · 0.044 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,8902025 | 2 Names on Record | AssessorUpdated May 2026 |
5 bd · 3,547 sqft · built 1910 · 0.103 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $315,800Sep 2006 | $7,4522025 | Amount on Record Jan 1995 | 1 Name on Record | AssessorUpdated May 2026 |
1 bd · 1,176 sqft · built 1915 · 0.119 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $585,000Aug 2021 | $8,9732025 | Amount on Record Apr 2018 | 1 Name on Record | Assessor + 2 DocumentsUpdated May 2026 |
2 bd · 7,996 sqft · built 1920 · 0.214 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,850,000Mar 2019 | $17,6062025 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
2 bd · 672 sqft · built 1952 · 0.173 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,7412025 | 1 Name on Record | Assessor + 1 DocumentUpdated May 2026 |
0.234 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,850,000Mar 2019 | $3,5132025 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
7,111 sqft · built 1952 · 0.43 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $19,1802025 | 1 Name on Record | Assessor + 1 DocumentUpdated May 2026 |
2 bd · 1,669 sqft · built 1925 · 0.23 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,0142025 | 1 Name on Record | AssessorUpdated May 2026 |
5 bd · 5 ba · 3,508 sqft · built 1933 · 0.248 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $4042025 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 5 ba · 3,159 sqft · built 1925 · 0.341 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $500,000Nov 2022 | $19,0282025 | Amount on Record Sep 2022 | 1 Name on Record | Assessor + 1 DocumentUpdated Jul 2026 |
2 bd · 2 ba · 1,494 sqft · built 1984 · 0.313 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $515,000Jul 2021 | $12,1792025 | Amount on Record May 1996 | 1 Name on Record | Assessor + 1 DocumentUpdated May 2026 |
6 bd · 4 ba · 2,466 sqft · built 2006 · 0.265 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $625,000Aug 2022 | $9,6542025 | Amount on Record Sep 2005 | 1 Name on Record | AssessorUpdated May 2026 |
4 bd · 3 ba · 2,185 sqft · built 1916 · 0.322 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $450,000Feb 2020 | $7,3772025 | Amount on Record Nov 2014 | 1 Name on Record | Assessor + 3 DocumentsUpdated Jul 2026 |
4 bd · 4 ba · 2,268 sqft · built 1993 · 0.317 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $739,000Aug 2025 | $7,0342025 | Amount on Record Apr 2003 | 1 Name on Record | AssessorUpdated May 2026 |
4 bd · 4 ba · 2,268 sqft · built 1993 · 0.317 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $739,000Jan 2026 | $7,0332025 | Amount on Record Apr 2003 | 1 Name on Record | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3 ba · 3,129 sqft · built 1920 · 0.344 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $24,500Apr 1994 | $1,3392025 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 1 ba · 1,310 sqft · built 1910 · 0.33 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $5722025 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
6 bd · 4 ba · 2,268 sqft · built 1993 · 0.317 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $100Jul 2016 | $7,7772025 | Amount on Record Mar 2010 | 1 Name on Record | AssessorUpdated May 2026 |
3 bd · 3,742 sqft · built 1910 · 0.395 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $505,000May 2018 | $13,6552025 | Amount on Record Aug 2007 | 1 Name on Record | Assessor + 1 DocumentUpdated May 2026 |
2 bd · 1 ba · 696 sqft · built 1984 · 0.165 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $100Jun 2016 | $3,3332025 | Amount on Record Jul 2007 | 1 Name on Record | AssessorUpdated May 2026 |
3 bd · 1.5 ba · 1,304 sqft · built 1959 · 0.405 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $100,000Dec 2009 | $5,6292025 | Amount on Record Aug 2006 | 1 Name on Record | AssessorUpdated May 2026 |
8 bd · 6.25 ba · 4,114 sqft · built 2015 · 0.224 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $300,000Sep 2015 | $4,4862025 | Amount on Record Nov 2013 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,895 sqft · built 2008 · 0.259 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $805,000Dec 2024 | $9,8042025 | Amount on Record Mar 2016 | 1 Name on Record | AssessorUpdated May 2026 |
6 bd · 2 ba · 1,990 sqft · built 1925 · 0.257 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $5,2212025 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
5 bd · 2 ba · 2,259 sqft · built 1914 · 0.328 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,1182025 | 1 Name on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
3 bd · 2.75 ba · 1,970 sqft · built 2023 · 0.152 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $650,000Feb 2024 | $7,9942025 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3.5 ba · 2,372 sqft · built 1955 · 0.148 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $275,000Apr 2025 | $2,3642025 | Amount on Record Jan 2020 | 1 Name on Record | Assessor + 3 DocumentsUpdated May 2026 |
2 bd · 1 ba · 1,335 sqft · built 1928 · 0.286 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $260,000Jun 2018 | $6,0632025 | Amount on Record Dec 1995 | 2 Names on Record | Assessor + 2 DocumentsUpdated May 2026 |
5 bd · 4 ba · 2,813 sqft · built 2020 · 0.322 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $750,000Dec 2025 | Amount on Record Dec 2020 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
7 bd · 4 ba · 2,892 sqft · built 1921 · 0.491 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $355,000May 2006 | $4,2782025 | Amount on Record Oct 1999 | 1 Name on Record | AssessorUpdated May 2026 |
4 bd · 2 ba · 1,590 sqft · built 1979 · 0.283 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $5,0442025 | 2 Names on Record | AssessorUpdated May 2026 |
3 bd · 2.5 ba · 2,062 sqft · built 2019 · 0.199 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $743,200Mar 2026 | $7,3682025 | Amount on Record Aug 2022 | 2 Names on Record Owner Occupied | Assessor + 8 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,454 sqft · built 2004 · 0.183 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $110,000Jul 2004 | $1,4332025 | Amount on Record Apr 2002 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
5 bd · 2 ba · 1,669 sqft · built 1959 · 0.328 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $237,400Sep 2015 | $5,7862025 | Amount on Record Jan 2014 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 2 ba · 2,178 sqft · built 1940 · 0.238 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $375,000Aug 2005 | $8332025 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 3 ba · 1,665 sqft · built 1906 · 0.245 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $245,500Jun 2005 | $4,3042025 | Amount on Record Jul 2003 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2.5 ba · 1,668 sqft · built 1954 · 0.13 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $120,000Jun 2017 | $1,6022025 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
4 bd · 2 ba · 2,284 sqft · built 1982 · 0.313 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,1222025 | 1 Name on Record | AssessorUpdated May 2026 |
2 bd · 2 ba · 1,153 sqft · built 1947 · 0.183 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,7232025 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 3 ba · 1,860 sqft · built 1983 · 0.313 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $5,5142025 | 1 Name on Record | AssessorUpdated May 2026 |
1,430 sqft · built 1946 · 0.198 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $350,000Oct 2019 | $7,3412025 | 1 Name on Record | Assessor + 2 DocumentsUpdated Jul 2026 |
1,648 sqft · built 1947 · 0.12 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $539,000Feb 2013 | $3,9682025 | Amount on Record Nov 2004 | 1 Name on Record | AssessorUpdated May 2026 |
4 bd · 3 ba · 1,860 sqft · built 1982 · 0.313 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $160,000May 2014 | $6,7662025 | Amount on Record Jul 1998 | 1 Name on Record | Assessor + 1 DocumentUpdated May 2026 |
5,200 sqft · built 1949 · 0.14 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $539,000Feb 2013 | $12,7972025 | Amount on Record Nov 2004 | 1 Name on Record | AssessorUpdated May 2026 |
0.156 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $580,000Jul 2025 | $1,4612025 | 1 Name on Record | AssessorUpdated May 2026 |
2 bd · 2 ba · 1,244 sqft · built 1952 · 0.26 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $375,000Jan 2022 | $5,0742025 | 1 Name on Record | Assessor + 2 DocumentsUpdated May 2026 |
8,052 sqft · built 2019 · 0.646 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $525,000Jan 2019 | $35,3552025 | Amount on Record Jun 2006 | 1 Name on Record | Assessor + 5 DocumentsUpdated May 2026 |
2 bd · 1 ba · 696 sqft · built 1984 · 0.162 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,7212025 | 2 Names on Record | AssessorUpdated May 2026 |
3 bd · 1 ba · 2,242 sqft · built 1925 · 0.262 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,5962025 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 1 ba · 1,276 sqft · built 1953 · 0.262 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,8002025 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
0.01 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $12025 | 1 Name on Record | AssessorUpdated May 2026 |
3 bd · 3 ba · 7,228 sqft · built 1960 · 0.6 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $8,8882025 | 2 Names on Record | Assessor + 3 DocumentsUpdated Jul 2026 |
2 bd · 1 ba · 912 sqft · built 1955 · 0.191 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $150,000Jul 2019 | $3,4212025 | Amount on Record Sep 2012 | 1 Name on Record | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,480 sqft · built 2006 · 0.194 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $150,000Mar 2015 | $4,6082025 | Amount on Record Apr 2010 | 1 Name on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jun 2026 |
2 bd · 1 ba · 1,040 sqft · built 1956 · 0.187 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $275,000Mar 2022 | $4,2772025 | Amount on Record Jun 2018 | 1 Name on Record | Assessor + 3 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,556 sqft · built 2005 · 0.177 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $190,000Oct 2005 | $4,6922025 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
2 bd · 1 ba · 795 sqft · built 1955 · 0.187 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3642025 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
0.23 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,1222025 | 1 Name on Record | AssessorUpdated May 2026 |
2 bd · 1 ba · 691 sqft · built 1953 · 0.187 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $250,000Feb 2022 | $2,6782025 | Amount on Record Mar 2021 | 1 Name on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
3 bd · 1 ba · 1,492 sqft · built 1953 · 0.19 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $229,000Aug 2019 | $4,7612025 | Amount on Record Mar 2017 | 1 Name on Record | Assessor + 2 DocumentsUpdated May 2026 |