St. Mary's County property records for 45 addresses on Woodmere Dr, Leonardtown, MD · Last verified October 2026
| Properties | 45 |
|---|---|
| Median Sale Price | $499,900 |
| Deeds and Mortgages on File | 63 |
| Median Price per Sqft | $226 |
| Owner Occupied | 100% |
| Median Annual Tax Bill | $4,064 |
| Median Year Built | 1998 |
| Median Ownership Tenure | 17 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20986 Woodmere Dr |
2.5 ba · 2,542 sqft built 1999 · 1.21 acres | $294,000 Mar 2004 | $4,442 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20990 Woodmere Dr |
3 ba · 2,404 sqft built 2001 · 0.739 acres | $499,900 Oct 2024 | $4,478 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20994 Woodmere Dr |
3.5 ba · 2,818 sqft built 2000 · 0.819 acres | $236,000 Jun 2001 | $5,089 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20998 Woodmere Dr |
3.5 ba · 2,608 sqft built 2000 · 1.33 acres | $252,589 Nov 2000 | $104 2025 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21002 Woodmere Dr |
3.5 ba · 3,125 sqft built 1998 · 0.767 acres | $248,000 Aug 2001 | $5,053 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21008 Woodmere Dr |
3.5 ba · 2,804 sqft built 1998 · 0.919 acres | $417,000 Apr 2007 | $5,306 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21012 Woodmere Dr |
2.5 ba · 2,448 sqft built 2001 · 0.729 acres | $399,900 Jun 2006 | $4,180 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21016 Woodmere Dr |
2.5 ba · 3,140 sqft built 2001 · 0.679 acres | $45,000 Jan 2002 | $4,438 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21020 Woodmere Dr |
2.5 ba · 3,176 sqft built 2002 · 0.6 acres | $299,685 Feb 2002 | $4,968 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21023 Woodmere Dr |
2.5 ba · 2,599 sqft built 1998 · 1.26 acres | $202,000 Mar 1998 | $4,709 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21024 Woodmere Dr |
2.5 ba · 2,132 sqft built 2001 · 0.829 acres | $299,900 Sep 2009 | $3,835 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21028 Woodmere Dr |
2.5 ba · 2,126 sqft built 1999 · 1.08 acres | $320,000 Jun 2016 | $4,118 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21032 Woodmere Dr |
2.5 ba · 2,579 sqft built 2001 · 0.9 acres | $340,000 Feb 2016 | $4,431 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21039 Woodmere Dr |
2.5 ba · 2,788 sqft built 1999 · 1.16 acres | $580,000 Jan 2026 | $4,531 2025 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21046 Woodmere Dr |
2.5 ba · 2,548 sqft built 2001 · 1.03 acres | $365,400 Nov 2018 | $104 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21051 Woodmere Dr |
2.5 ba · 2,538 sqft built 1997 · 1.46 acres | $445,000 Aug 2020 | $4,398 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21052 Woodmere Dr |
2.5 ba · 2,246 sqft built 2001 · 0.7 acres | $300,500 Jan 2011 | $4,064 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21056 Woodmere Dr |
2.5 ba · 2,205 sqft built 1999 · 0.869 acres | $500,000 Oct 2025 | $4,330 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21060 Woodmere Dr |
3.5 ba · 2,525 sqft built 2001 · 0.989 acres | $575,000 Mar 2026 | $4,950 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21064 Woodmere Dr |
3.5 ba · 3,042 sqft built 1999 · 1.1 acres | — Aug 2021 | $4,920 2025 | Assessor + 7 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21090 Woodmere Dr |
0.709 acres | $446,000 Sep 1996 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21100 Woodmere Dr |
2.5 ba · 2,129 sqft built 2014 · 0.95 acres | $317,500 Oct 2015 | $4,220 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21104 Woodmere Dr |
2.5 ba · 2,048 sqft built 2013 · 0.8 acres | $319,000 Oct 2014 | $4,205 2025 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21110 Woodmere Dr |
3 ba · 2,356 sqft built 1994 · 0.459 acres | $122,000 Feb 1997 | $4,300 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21117 Woodmere Dr |
3 ba · 1,696 sqft built 1994 · 0.609 acres | $28,000 Jan 2004 | $3,552 2025 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21120 Woodmere Dr |
3.5 ba · 1,240 sqft built 1992 · 0.459 acres | $118,500 Jul 1992 | $3,796 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21129 Woodmere Dr |
2 ba · 2,098 sqft built 1997 · 0.459 acres | $285,000 Aug 2020 | $3,893 2025 | Assessor + 3 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21130 Woodmere Dr |
3 ba · 1,198 sqft built 1993 · 0.939 acres | $320,000 Sep 2020 | $3,670 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21133 Woodmere Dr |
3 ba · 1,318 sqft built 1998 · 0.459 acres | $339,000 Mar 2021 | $3,651 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21164 Woodmere Dr |
3 ba · 1,800 sqft built 1990 · 0.458 acres | $121,000 May 1993 | $3,549 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21174 Woodmere Dr |
2 ba · 1,788 sqft built 1990 · 0.45 acres | $157,150 Jun 1997 | $3,435 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21184 Woodmere Dr |
2 ba · 1,392 sqft built 1991 · 0.45 acres | $205,000 Jun 2004 | $3,003 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21194 Woodmere Dr |
3 ba · 1,524 sqft built 1991 · 0.45 acres | $365,000 Aug 2019 | $4,561 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21209 Woodmere Dr |
2 ba · 1,824 sqft built 1989 · 0.914 acres | $163,500 Oct 1998 | $3,535 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21214 Woodmere Dr |
2 ba · 1,788 sqft built 1990 · 0.479 acres | $122,000 Jun 1990 | $3,059 2025 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21224 Woodmere Dr |
2 ba · 1,728 sqft built 1990 · 0.489 acres | $127,000 Oct 1998 | $3,337 2025 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21227 Woodmere Dr |
1 ba · 2,985 sqft built 1990 · 0.459 acres | $124,900 Mar 1998 | $104 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21234 Woodmere Dr |
2 ba · 1,480 sqft built 1990 · 0.489 acres | $249,989 Feb 2018 | $3,216 2025 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21244 Woodmere Dr |
2 ba · 1,480 sqft built 1989 · 0.519 acres | — Oct 2020 | $3,042 2025 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21254 Woodmere Dr |
3 ba · 1,296 sqft built 1990 · 0.569 acres | $270,000 Jul 2017 | $3,408 2025 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21273 Woodmere Dr |
2.5 ba · 2,128 sqft built 1987 · 2.88 acres | — Sep 1985 | $3,804 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21274 Woodmere Dr |
2 ba · 1,296 sqft built 1990 · 0.45 acres | $205,000 Apr 2017 | $3,105 2025 | Assessor + 3 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21276 Woodmere Dr |
1.5 ba · 1,120 sqft built 1984 · 28.3 acres | — Aug 1990 | $4,129 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21279 Woodmere Dr |
2 ba · 1,491 sqft built 1990 · 3.81 acres | $3,535 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21284 Woodmere Dr |
3 ba · 1,254 sqft built 1991 · 0.457 acres | $280,000 Dec 2019 | $3,707 2025 | Assessor + 4 Documents Updated Sep 2026 | Owner on File Owner Occupied |