St. Mary's County property records for 51 addresses on Chestnut Ridge Dr, Leonardtown, MD · Last verified October 2026
| Properties | 51 |
|---|---|
| Median Sale Price | $550,000 |
| Deeds and Mortgages on File | 69 |
| Median Price per Sqft | $208 |
| Owner Occupied | 96% |
| Median Annual Tax Bill | $4,748 |
| Median Year Built | 1993 |
| Median Ownership Tenure | 14 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20479 Chestnut Ridge Dr |
3 ba · 2,040 sqft built 1994 · 4.81 acres | $350,000 Apr 2013 | $4,648 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20480 Chestnut Ridge Dr |
4.5 ba · 3,602 sqft built 1996 · 3.36 acres | — Feb 2006 | $5,778 2025 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20482 Chestnut Ridge Dr |
3 ba · 2,361 sqft built 1997 · 2.86 acres | $58,000 Sep 1996 | $4,799 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20483 Chestnut Ridge Dr |
2.5 ba · 2,908 sqft built 1993 · 3.03 acres | $415,000 Jun 2019 | $5,971 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20484 Chestnut Ridge Dr |
3 ba · 1,744 sqft built 1993 · 2.26 acres | $275,000 Nov 2022 | $3,796 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20485 Chestnut Ridge Dr |
3 ba · 2,024 sqft built 1993 · 2.58 acres | $410,000 Jun 2020 | $4,462 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20490 Chestnut Ridge Dr |
3.5 ba · 2,036 sqft built 1993 · 2.81 acres | $40,500 Mar 1993 | $4,935 2025 | Assessor Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20496 Chestnut Ridge Dr |
4.5 ba · 2,505 sqft built 1993 · 2.4 acres | $410,000 Sep 2017 | $4,549 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20499 Chestnut Ridge Dr |
3 ba · 1,800 sqft built 1994 · 2.31 acres | $345,000 Oct 2017 | $4,748 2025 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20500 Chestnut Ridge Dr |
3 ba · 2,044 sqft built 1995 · 2.31 acres | $435,000 Sep 2007 | $4,801 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20503 Chestnut Ridge Dr |
2.5 ba · 1,848 sqft built 1993 · 3.03 acres | $39,000 Jun 1993 | $4,234 2025 | Assessor Updated Sep 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20507 Chestnut Ridge Dr |
3 ba · 1,705 sqft built 1994 · 4.18 acres | $355,000 Sep 2012 | $4,414 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20511 Chestnut Ridge Dr |
3.5 ba · 3,798 sqft built 1995 · 3.76 acres | $43,000 Apr 1993 | $5,869 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20520 Chestnut Ridge Dr |
2.5 ba · 2,325 sqft built 1995 · 2.21 acres | $550,000 Jun 2022 | $5,904 2025 | Assessor + 3 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20525 Chestnut Ridge Dr |
3 ba · 2,544 sqft built 1994 · 2.03 acres | $227,000 Aug 1996 | $4,691 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20535 Chestnut Ridge Dr |
3 ba · 2,515 sqft built 1999 · 2.18 acres | $47,000 Dec 1998 | $4,590 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20550 Chestnut Ridge Dr |
2.5 ba · 2,742 sqft built 1996 · 2.23 acres | $573,000 Apr 2026 | $4,595 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20565 Chestnut Ridge Dr |
3 ba · 2,656 sqft built 1996 · 2.53 acres | $495,000 Feb 2006 | $5,316 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20572 Chestnut Ridge Dr |
3.5 ba · 3,840 sqft built 1993 · 6.63 acres | $458,000 Dec 2008 | $5,633 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20576 Chestnut Ridge Dr |
2.5 ba · 2,688 sqft built 1994 · 5.76 acres | $510,000 Nov 2020 | $5,599 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20590 Chestnut Ridge Dr |
3 ba · 2,846 sqft built 1995 · 2.35 acres | $475,000 Sep 2007 | $4,740 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20591 Chestnut Ridge Dr |
3.5 ba · 3,061 sqft built 1995 · 2.11 acres | $599,900 Nov 2025 | $5,806 2025 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20610 Chestnut Ridge Dr |
2.5 ba · 3,021 sqft built 1994 · 4.01 acres | $580,000 Sep 2022 | $6,320 2025 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20644 Chestnut Ridge Dr |
2.5 ba · 5,104 sqft built 1991 · 2.18 acres | — Jun 1998 | $6,398 2025 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20676 Chestnut Ridge Dr |
2.5 ba · 1,792 sqft built 1992 · 2.31 acres | $223,000 Dec 2002 | $3,770 2025 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20704 Chestnut Ridge Dr |
3.5 ba · 3,642 sqft built 1994 · 6.35 acres | $275,000 Jul 2014 | $5,580 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20708 Chestnut Ridge Dr |
2.5 ba · 2,580 sqft built 2001 · 9.68 acres | $64,000 Jun 2000 | $4,337 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20714 Chestnut Ridge Dr |
2.5 ba · 2,268 sqft built 1992 · 2.16 acres | $34,000 Mar 1991 | $4,415 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20735 Chestnut Ridge Dr |
3 ba · 2,568 sqft built 1992 · 2 acres | $362,500 Jul 2013 | $5,453 2025 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20740 Chestnut Ridge Dr |
3 ba · 2,922 sqft built 1991 · 2.26 acres | $599,980 Aug 2024 | $5,245 2025 | Assessor + 4 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20753 Chestnut Ridge Dr |
2.5 ba · 2,474 sqft built 1994 · 2 acres | $560,000 Mar 2026 | $164 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20760 Chestnut Ridge Dr |
3 ba · 2,466 sqft built 1993 · 2.31 acres | $550,000 Feb 2024 | $5,249 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20776 Chestnut Ridge Dr |
3 ba · 2,606 sqft built 1991 · 8.23 acres | $339,900 Sep 2017 | $4,899 2025 | Assessor + 4 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20784 Chestnut Ridge Dr |
3 ba · 2,102 sqft built 1992 · 2.46 acres | $369,000 Jan 2019 | $164 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20787 Chestnut Ridge Dr |
2.5 ba · 2,602 sqft built 1992 · 2 acres | $207,500 Sep 1996 | $4,382 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20800 Chestnut Ridge Dr |
2.5 ba · 2,820 sqft built 1991 · 7.85 acres | $559,900 Aug 2006 | $5,588 2025 | Assessor + 3 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20804 Chestnut Ridge Dr |
3 ba · 2,932 sqft built 1992 · 5.6 acres | $440,000 Nov 2008 | $164 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20815 Chestnut Ridge Dr |
2 ba · 1,620 sqft built 1992 · 2.11 acres | $449,900 May 2023 | $4,221 2025 | Assessor + 3 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20820 Chestnut Ridge Dr |
2.5 ba · 2,416 sqft built 1990 · 2.06 acres | $32,500 Sep 1990 | $4,325 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20829 Chestnut Ridge Dr |
3.5 ba · 3,683 sqft built 1991 · 2.13 acres | $395,000 Dec 2013 | $5,657 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20849 Chestnut Ridge Dr |
3.5 ba · 2,971 sqft built 1991 · 4.81 acres | — Oct 2002 | $5,532 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20854 Chestnut Ridge Dr |
3 ba · 1,880 sqft built 1992 · 2.76 acres | $340,000 May 2012 | $4,278 2025 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20857 Chestnut Ridge Dr |
3 ba · 2,654 sqft built 1994 · 3.05 acres | $495,000 Aug 2005 | $4,907 2025 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20871 Chestnut Ridge Dr |
3.5 ba · 2,996 sqft built 1992 · 3.28 acres | $450,000 Apr 2013 | $5,605 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20892 Chestnut Ridge Dr |
3.5 ba · 3,824 sqft built 1991 · 3 acres | $267,000 Apr 1997 | $6,090 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20899 Chestnut Ridge Dr |
3.5 ba · 2,376 sqft built 1994 · 2.53 acres | $385,000 Oct 2013 | $5,434 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20913 Chestnut Ridge Dr |
2.5 ba · 1,848 sqft built 1992 · 2.43 acres | $35,000 Jan 1992 | $4,024 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20920 Chestnut Ridge Dr |
2.5 ba · 1,628 sqft built 1990 · 2.18 acres | $279,900 Feb 2004 | $3,824 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20947 Chestnut Ridge Dr |
3 ba · 1,386 sqft built 1991 · 2.61 acres | $485,000 Feb 2023 | $4,706 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20970 Chestnut Ridge Dr |
2 ba · 2,074 sqft built 1991 · 2.01 acres | $172,900 Dec 1992 | $3,668 2025 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20995 Chestnut Ridge Dr |
3 ba · 2,149 sqft built 1996 · 2.38 acres | $475,000 Jan 2024 | $4,600 2025 | Assessor + 4 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |