Orange County property records for 67 addresses on Woodcrest Dr, Winter Park, FL · Last verified October 2026
| Properties | 84 |
|---|---|
| Median Sale Price | $240,000 |
| Deeds and Mortgages on File | 105 |
| Median Price per Sqft | $237 |
| Owner Occupied | 64% |
| Median Annual Tax Bill | $3,294 |
| Median Year Built | 1962 |
| Median Ownership Tenure | 9 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1911, Unit A Woodcrest Dr |
2 bd · 2.25 ba · 987 sqft built 1973 · 0.642 acres | $255,000 Feb 2023 | $1,714 2025 | Assessor Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1913, Unit B Woodcrest Dr |
2 bd · 2.25 ba · 987 sqft built 1973 · 0.642 acres | $197,400 Mar 2026 | $2,389 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1915, Unit D Woodcrest Dr |
2 bd · 2.25 ba · 987 sqft built 1973 · 0.642 acres | $221,000 Nov 2022 | $2,645 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1917, #C Woodcrest Dr |
2 bd · 2.25 ba · 987 sqft built 1973 · 0.642 acres | $98,000 Mar 2015 | $3,003 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1919, #1 Woodcrest Dr |
2 bd · 1.75 ba · 987 sqft built 1973 · 0.642 acres | $235,000 May 2023 | $2,645 2025 | Assessor + 1 Document Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1920 Woodcrest Dr |
$2 2025 | Assessor Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1920 Woodcrest Dr |
18 units · 768 sq ft Built 1969 | $255,000 Oct 2025 | $2,458 2025 |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1921, #2 Woodcrest Dr |
2 bd · 1.75 ba · 987 sqft built 1973 · 0.642 acres | $95,000 Nov 2009 | $2,932 2025 | Assessor Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1923, #3 Woodcrest Dr |
2 bd · 1.75 ba · 987 sqft built 1973 · 0.642 acres | $1,400 Mar 2021 | $2,172 2025 | Assessor + 3 Documents Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1925, #E Woodcrest Dr |
2 bd · 2.25 ba · 987 sqft built 1973 · 0.642 acres | $240,000 Jul 2023 | $3,271 2025 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1927, #F Woodcrest Dr |
2 bd · 2.25 ba · 987 sqft built 1973 · 0.642 acres | $137,500 Aug 2017 | $1,381 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1929, #H Woodcrest Dr |
2 bd · 2.25 ba · 987 sqft built 1973 · 0.642 acres | $170,000 Jan 2021 | $1,911 2025 | Assessor + 1 Document Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1931, #G Woodcrest Dr |
2 bd · 2.25 ba · 987 sqft built 1973 · 0.642 acres | $95,000 Mar 2015 | $3,003 2025 | Assessor + 1 Document Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1933 Woodcrest Dr |
3 bd · 2.5 ba · 2,310 sqft built 2019 · 0.186 acres | $675,000 Jul 2019 | $7,599 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1934 Woodcrest Dr |
0.174 acres | $158 2025 | Assessor Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1935 Woodcrest Dr |
4 bd · 3.5 ba · 2,430 sqft built 2019 · 0.182 acres | $744,800 Jun 2019 | $8,895 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1936 Woodcrest Dr |
2 bd · 2 ba · 1,250 sqft built 1981 · 0.06 acres | $86,000 Mar 2000 | $1,316 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1937 Woodcrest Dr |
3 bd · 3.5 ba · 2,620 sqft built 2019 · 0.182 acres | $788,571 Dec 2019 | $11,010 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1938 Woodcrest Dr |
3 bd · 2.5 ba · 1,694 sqft built 1981 · 0.045 acres | $265,000 Oct 2020 | $3,294 2025 | Assessor + 2 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1939 Woodcrest Dr |
3 bd · 3.5 ba · 2,368 sqft built 2020 · 0.186 acres | $1,170,000 Apr 2024 | $15,488 2025 | Assessor + 3 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1940 Woodcrest Dr |
3 bd · 2.5 ba · 1,694 sqft built 1981 · 0.04 acres | $1,076 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1941 Woodcrest Dr |
3 bd · 2 ba · 1,611 sqft built 1960 · 0.232 acres | $1,428 Jun 2021 | $7,398 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1947 Woodcrest Dr |
4 bd · 2.5 ba · 1,734 sqft built 1960 · 0.232 acres | $435,000 Apr 2021 | $7,595 2025 | Assessor + 2 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1955 Woodcrest Dr |
3 bd · 2.5 ba · 1,610 sqft built 1960 · 0.232 acres | $132,000 Sep 2000 | $2,101 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2003 Woodcrest Dr |
4 bd · 2.5 ba · 1,734 sqft built 1961 · 0.232 acres | $719,000 Mar 2025 | $5,610 2025 | Assessor + 2 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2004 Woodcrest Dr |
3 bd · 3 ba · 1,688 sqft built 1959 · 0.287 acres | $110,000 Feb 1998 | $2,584 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2009 Woodcrest Dr |
4 bd · 2.5 ba · 1,769 sqft built 1960 · 0.232 acres | $40,000 Dec 2017 | $2,831 2025 | Assessor + 3 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2012 Woodcrest Dr |
3 bd · 2 ba · 1,623 sqft built 1959 · 0.253 acres | $455,000 Jan 2021 | $6,719 2025 | Assessor + 3 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2015 Woodcrest Dr |
3 bd · 2 ba · 1,461 sqft built 1959 · 0.232 acres | $100 May 2017 | $5,550 2025 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2018 Woodcrest Dr |
3 bd · 2 ba · 1,566 sqft built 1959 · 0.254 acres | $400,000 Jan 2025 | $6,533 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2021 Woodcrest Dr |
4 bd · 2 ba · 1,425 sqft built 1959 · 0.232 acres | $6,782 2025 | Assessor Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2026 Woodcrest Dr |
3 bd · 2 ba · 1,749 sqft built 1962 · 0.267 acres | $2,339 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2027 Woodcrest Dr |
4 bd · 2 ba · 2,041 sqft built 1960 · 0.243 acres | $250,000 Aug 2012 | $4,496 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2032 Woodcrest Dr |
4 bd · 2 ba · 1,812 sqft built 1960 · 0.268 acres | $63,450 Aug 2020 | $4,444 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2105 Woodcrest Dr |
3 bd · 2 ba · 1,533 sqft built 1960 · 0.235 acres | $370,500 Jul 2018 | $8,276 2025 | Assessor + 3 Documents Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2106 Woodcrest Dr |
3 bd · 2 ba · 1,585 sqft built 1960 · 0.246 acres | $7,240 Nov 2021 | $5,148 2025 | Assessor + 1 Document Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2111 Woodcrest Dr |
3 bd · 2 ba · 1,665 sqft built 1959 · 0.247 acres | $240,000 May 2012 | $4,087 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2114 Woodcrest Dr |
3 bd · 2 ba · 1,666 sqft built 1960 · 0.247 acres | $235,000 Jun 2014 | $6,640 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2119 Woodcrest Dr |
3 bd · 2 ba · 1,629 sqft built 1960 · 0.247 acres | $122,000 May 2015 | $4,995 2025 | Assessor Updated Jun 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2120 Woodcrest Dr |
3 bd · 2 ba · 1,942 sqft built 1960 · 0.248 acres | $376,000 May 2017 | $5,658 2025 | Assessor + 5 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2125 Woodcrest Dr |
4 bd · 3 ba · 2,275 sqft built 1959 · 0.247 acres | $345,000 Sep 2012 | $5,282 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2126 Woodcrest Dr |
3 bd · 2 ba · 1,857 sqft built 1960 · 0.249 acres | $397,500 Apr 2023 | $5,209 2025 | Assessor + 1 Document Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2133 Woodcrest Dr |
3 bd · 2 ba · 1,515 sqft built 1959 · 0.247 acres | $1,709 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2134 Woodcrest Dr |
4 bd · 2 ba · 1,443 sqft built 1960 · 0.249 acres | $99,900 Oct 1996 | $1,989 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2201 Woodcrest Dr |
3 bd · 2 ba · 1,586 sqft built 1960 · 0.247 acres | $205,400 Mar 2025 | $6,254 2025 | Assessor + 2 Documents Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2202 Woodcrest Dr |
4 bd · 2 ba · 1,827 sqft built 1959 · 0.25 acres | $72,000 Jan 2004 | $6,198 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2215 Woodcrest Dr |
4 bd · 2 ba · 1,688 sqft built 1960 · 0.244 acres | $100 Oct 2016 | $4,089 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2216 Woodcrest Dr |
3 bd · 2 ba · 1,608 sqft built 1960 · 0.251 acres | $625,000 Sep 2023 | $8,155 2025 | Assessor + 4 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2223 Woodcrest Dr |
4 bd · 2 ba · 1,600 sqft built 1959 · 0.248 acres | $235,051 Dec 2016 | $3,990 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2228 Woodcrest Dr |
3 bd · 2.5 ba · 1,712 sqft built 1960 · 0.252 acres | $125,000 Oct 1998 | $8,102 2025 | Assessor Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2229 Woodcrest Dr |
4 bd · 2 ba · 1,428 sqft built 1960 · 0.248 acres | $230,000 Jan 2017 | $6,216 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2230 Woodcrest Dr |
3 bd · 2 ba · 1,782 sqft built 1960 · 0.252 acres | $2,201 2025 | Assessor + 1 Document Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2237 Woodcrest Dr |
3 bd · 2 ba · 1,492 sqft built 1959 · 0.248 acres | $490,000 Jun 2026 | $1,918 2025 | Assessor + 3 Documents Updated Jun 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2238 Woodcrest Dr |
4 bd · 3 ba · 2,079 sqft built 1960 · 0.243 acres | $239,000 Aug 2003 | $3,324 2025 | Assessor + 1 Document Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2307 Woodcrest Dr |
3 bd · 2 ba · 1,732 sqft built 1960 · 0.248 acres | $3,628 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2308 Woodcrest Dr |
3 bd · 2.5 ba · 1,711 sqft built 1959 · 0.274 acres | $225,000 Feb 2013 | $8,185 2025 | Assessor + 1 Document Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2313 Woodcrest Dr |
3 bd · 2 ba · 1,676 sqft built 1959 · 0.248 acres | $180,000 Sep 2011 | $2,724 2025 | Assessor + 4 Documents Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2314 Woodcrest Dr |
3 bd · 2 ba · 2,385 sqft built 1962 · 0.238 acres | $325,000 Apr 2013 | $5,222 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2321 Woodcrest Dr |
3 bd · 2 ba · 1,909 sqft built 1959 · 0.235 acres | $1,877 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2322 Woodcrest Dr |
4 bd · 2 ba · 1,650 sqft built 1963 · 0.262 acres | $586,000 Dec 2022 | $5,827 2025 | Assessor + 3 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2332 Woodcrest Dr |
4 bd · 2 ba · 1,813 sqft built 1961 · 0.256 acres | $290,000 Jun 2015 | $4,590 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2335 Woodcrest Dr |
3 bd · 2 ba · 1,570 sqft built 1960 · 0.235 acres | $200,000 Aug 2011 | $2,901 2025 | Assessor + 1 Document Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2336 Woodcrest Dr |
3 bd · 2 ba · 1,631 sqft built 1960 · 0.257 acres | $161,000 Aug 2001 | $5,958 2025 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2343 Woodcrest Dr |
3 bd · 2 ba · 1,779 sqft built 1960 · 0.248 acres | $370,000 Mar 2018 | $5,302 2025 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2344 Woodcrest Dr |
3 bd · 2 ba · 1,714 sqft built 1960 · 0.258 acres | $408,000 Sep 2021 | $6,366 2025 | Assessor + 4 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2351 Woodcrest Dr |
4 bd · 2.5 ba · 2,074 sqft built 1964 · 0.247 acres | $472,000 May 2024 | $7,225 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2352 Woodcrest Dr |
5 bd · 2.5 ba · 2,379 sqft built 1969 · 0.261 acres | $315,000 Jul 2008 | $9,185 2025 | Assessor Updated May 2026 | 2 Owners on File |