Orange County property records for 61 addresses on Winding Oaks Dr, Orlando, FL · Last verified October 2026
| Properties | 61 |
|---|---|
| Median Sale Price | $580,000 |
| Deeds and Mortgages on File | 73 |
| Median Price per Sqft | $199 |
| Owner Occupied | 93% |
| Median Annual Tax Bill | $5,368 |
| Median Year Built | 2003 |
| Median Ownership Tenure | 11 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1700 Winding Oaks Dr |
4 bd · 2 ba · 2,317 sqft built 2002 · 0.268 acres | $265,000 Jan 2005 | $3,160 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1701 Winding Oaks Dr |
4 bd · 3 ba · 3,178 sqft built 2003 · 0.258 acres | $395,000 Jan 2020 | $9,418 2025 | Assessor + 3 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1706 Winding Oaks Dr |
4 bd · 3 ba · 3,084 sqft built 2002 · 0.27 acres | $266,200 Nov 2002 | $4,014 2025 | Assessor Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1707 Winding Oaks Dr |
4 bd · 4.5 ba · 2,891 sqft built 2003 · 0.234 acres | — Sep 2020 | $400 2025 | Assessor + 3 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1712 Winding Oaks Dr |
4 bd · 3 ba · 2,550 sqft built 2002 · 0.295 acres | $344,000 Dec 2007 | $3,682 2025 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1713 Winding Oaks Dr |
4 bd · 3 ba · 2,926 sqft built 2003 · 0.234 acres | $580,000 Jul 2026 | $7,095 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1718 Winding Oaks Dr |
6 bd · 4 ba · 3,622 sqft built 2002 · 0.316 acres | $373,000 Mar 2016 | $8,698 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1719 Winding Oaks Dr |
4 bd · 3 ba · 2,684 sqft built 2002 | $236,000 Jun 2012 | $4,185 2025 | Assessor + 1 Document Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1724 Winding Oaks Dr |
4 bd · 4 ba · 2,956 sqft built 2003 · 0.318 acres | $480,000 Apr 2006 | $9,966 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1725 Winding Oaks Dr |
4 bd · 3 ba · 2,553 sqft built 2003 · 0.258 acres | $346,000 Aug 2018 | $5,430 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1730 Winding Oaks Dr |
5 bd · 3 ba · 3,306 sqft built 2002 · 0.355 acres | $240,000 Feb 2010 | $4,556 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1731 Winding Oaks Dr |
4 bd · 3 ba · 2,686 sqft built 2002 · 0.258 acres | $323,000 Oct 2017 | $5,040 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1736 Winding Oaks Dr |
5 bd · 3 ba · 3,164 sqft built 2003 · 0.356 acres | $425,000 Sep 2020 | $6,583 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1737 Winding Oaks Dr |
5 bd · 3.5 ba · 3,257 sqft built 2002 · 0.234 acres | $405,000 Sep 2018 | $5,586 2025 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1743 Winding Oaks Dr |
4 bd · 3 ba · 3,184 sqft built 2003 · 0.234 acres | $299,900 Jan 2005 | $5,469 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1803 Winding Oaks Dr |
4 bd · 3 ba · 2,918 sqft built 2003 · 0.234 acres | $320,000 May 2016 | $5,931 2025 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1809 Winding Oaks Dr |
4 bd · 3 ba · 2,918 sqft built 2003 · 0.256 acres | $489,000 Jan 2006 | $4,432 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1814 Winding Oaks Dr |
4 bd · 3 ba · 2,711 sqft built 2001 · 0.382 acres | $4,279 2025 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1815 Winding Oaks Dr |
4 bd · 3 ba · 2,717 sqft built 2003 · 0.263 acres | $675,000 Apr 2026 | $6,231 2025 | Assessor + 5 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1820 Winding Oaks Dr |
4 bd · 3 ba · 3,017 sqft built 2000 · 0.274 acres | $339,100 Dec 2001 | $4,610 2025 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1821 Winding Oaks Dr |
4 bd · 3 ba · 2,567 sqft built 2003 · 0.263 acres | $247,000 Apr 2003 | $3,567 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1826 Winding Oaks Dr |
4 bd · 3 ba · 2,696 sqft built 2001 · 0.238 acres | $335,000 Jul 2016 | $400 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1827 Winding Oaks Dr |
4 bd · 3 ba · 3,385 sqft built 2003 · 0.25 acres | $294,100 Jun 2003 | $4,814 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1832 Winding Oaks Dr |
5 bd · 3 ba · 2,824 sqft built 2002 · 0.234 acres | $425,000 Jul 2019 | $6,048 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1833 Winding Oaks Dr |
4 bd · 3 ba · 2,664 sqft built 2002 · 0.234 acres | $319,000 Feb 2018 | $400 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1838 Winding Oaks Dr |
4 bd · 3 ba · 2,743 sqft built 2002 · 0.234 acres | $273,100 Jan 2002 | $3,977 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1839 Winding Oaks Dr |
4 bd · 3 ba · 2,918 sqft built 2003 · 0.234 acres | $585,000 Aug 2023 | $9,627 2025 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1844 Winding Oaks Dr |
4 bd · 2 ba · 3,208 sqft built 2002 · 0.234 acres | $100 Nov 2016 | $9,590 2025 | Assessor Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1845 Winding Oaks Dr |
4 bd · 3 ba · 2,554 sqft built 2003 · 0.271 acres | $473,000 Nov 2006 | $4,319 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1850 Winding Oaks Dr |
4 bd · 3 ba · 3,154 sqft built 2002 · 0.234 acres | $440,000 May 2019 | $10,194 2025 | Assessor + 1 Document Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1900 Winding Oaks Dr |
4 bd · 3.5 ba · 3,188 sqft built 2002 · 0.234 acres | $379,000 Jul 2015 | $5,541 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1901 Winding Oaks Dr |
4 bd · 3 ba · 2,360 sqft built 2003 · 0.265 acres | $637,000 Jun 2026 | $8,859 2025 | Assessor + 1 Document Updated Jun 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1905 Winding Oaks Dr |
4 bd · 3 ba · 2,717 sqft built 2003 · 0.255 acres | $326,000 Jan 2018 | $5,776 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1906 Winding Oaks Dr |
5 bd · 3 ba · 2,953 sqft built 2003 · 0.238 acres | $140,000 Aug 2004 | $4,824 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1907 Winding Oaks Dr |
4 bd · 3 ba · 2,554 sqft built 2003 · 0.244 acres | $286,600 Feb 2003 | $4,015 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1912 Winding Oaks Dr |
4 bd · 3 ba · 2,717 sqft built 2003 · 0.234 acres | $245,000 Oct 2010 | $9,014 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1913 Winding Oaks Dr |
4 bd · 3 ba · 2,717 sqft built 2003 · 0.234 acres | $450,000 Sep 2020 | $8,860 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1918 Winding Oaks Dr |
4 bd · 3 ba · 2,620 sqft built 2003 · 0.234 acres | $252,000 Mar 2011 | $5,393 2025 | Assessor + 3 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1919 Winding Oaks Dr |
4 bd · 3 ba · 2,556 sqft built 2002 · 0.234 acres | $650,000 Oct 2025 | $8,439 2025 | Assessor + 4 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1924 Winding Oaks Dr |
4 bd · 4 ba · 3,440 sqft built 2003 · 0.234 acres | $303,100 Mar 2003 | $5,368 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1925 Winding Oaks Dr |
4 bd · 4 ba · 3,382 sqft built 2002 · 0.234 acres | $327,000 Jun 2004 | $4,817 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1930 Winding Oaks Dr |
4 bd · 4 ba · 3,096 sqft built 2003 · 0.234 acres | $405,000 Feb 2018 | $5,743 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1931 Winding Oaks Dr |
4 bd · 3 ba · 2,472 sqft built 2002 · 0.234 acres | $290,000 May 2014 | $5,098 2025 | Assessor + 3 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1936 Winding Oaks Dr |
4 bd · 3 ba · 2,900 sqft built 2003 · 0.234 acres | $449,000 Jul 2006 | $4,575 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1937 Winding Oaks Dr |
4 bd · 4 ba · 3,382 sqft built 2002 · 0.234 acres | $430,000 Jul 2020 | $7,100 2025 | Assessor + 1 Document Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1942 Winding Oaks Dr |
4 bd · 3 ba · 3,115 sqft built 2002 · 0.234 acres | $450,000 Oct 2018 | $9,986 2025 | Assessor + 5 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1943 Winding Oaks Dr |
4 bd · 4 ba · 3,115 sqft built 2002 · 0.258 acres | $264,900 Aug 2004 | $4,690 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1948 Winding Oaks Dr |
4 bd · 4.5 ba · 4,145 sqft built 2003 · 0.234 acres | $325,000 Jul 2013 | $7,838 2025 | Assessor + 1 Document Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2002 Winding Oaks Dr |
4 bd · 3 ba · 3,187 sqft built 2003 · 0.247 acres | $474,000 Apr 2019 | $9,773 2025 | Assessor + 4 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2003 Winding Oaks Dr |
4 bd · 3 ba · 3,035 sqft built 2003 · 0.272 acres | $354,000 Nov 2015 | $6,080 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2008 Winding Oaks Dr |
4 bd · 4 ba · 3,440 sqft built 2003 · 0.275 acres | $375,800 Jul 2013 | $5,937 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2013 Winding Oaks Dr |
4 bd · 4.5 ba · 3,099 sqft built 2003 · 0.249 acres | $311,709 May 2015 | $4,706 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2014 Winding Oaks Dr |
4 bd · 3 ba · 2,559 sqft built 2003 · 0.263 acres | $510,000 Jul 2021 | $6,366 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2019 Winding Oaks Dr |
4 bd · 3 ba · 3,035 sqft built 2003 · 0.244 acres | $266,200 Aug 2003 | $4,570 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2020 Winding Oaks Dr |
4 bd · 3 ba · 3,123 sqft built 2003 · 0.239 acres | $465,000 Feb 2021 | $6,344 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2025 Winding Oaks Dr |
4 bd · 3 ba · 2,685 sqft built 2003 · 0.288 acres | $242,800 Aug 2003 | $3,629 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2026 Winding Oaks Dr |
4 bd · 3 ba · 3,035 sqft built 2003 · 0.234 acres | $400,000 Nov 2006 | $4,085 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2031 Winding Oaks Dr |
4 bd · 4 ba · 3,440 sqft built 2003 · 0.311 acres | $289,600 Aug 2003 | $4,533 2025 | Assessor + 2 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2032 Winding Oaks Dr |
4 bd · 4.5 ba · 3,099 sqft built 2003 · 0.276 acres | $317,100 Oct 2003 | $4,910 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2037 Winding Oaks Dr |
5 bd · 3.5 ba · 3,703 sqft built 2003 · 0.306 acres | $349,300 Oct 2003 | $400 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2038 Winding Oaks Dr |
4 bd · 3 ba · 2,580 sqft built 2003 · 0.307 acres | $590,000 Feb 2025 | $3,528 2025 | Assessor + 1 Document Updated Oct 2026 | Owner on File Owner Occupied |