Kent County property records for 55 addresses on Chestertown Rd, Chestertown, MD · Last verified October 2026
| Properties | 55 |
|---|---|
| Median Sale Price | $265,000 |
| Deeds and Mortgages on File | 76 |
| Median Price per Sqft | $181 |
| Owner Occupied | 87% |
| Median Annual Tax Bill | $2,817 |
| Median Year Built | 1962 |
| Median Ownership Tenure | 12 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
23262 Chestertown Rd |
2 ba · 2,510 sqft built 1900 · 1.93 acres | $170,000 Jun 2019 | $3,278 2026 | Assessor + 5 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
23310 Chestertown Rd |
3 ba · 2,348 sqft built 1988 · 2.43 acres | $250,000 Sep 2015 | $3,332 2026 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
23315 Chestertown Rd |
2 ba · 2,318 sqft built 1939 · 2.91 acres | $52,500 May 1977 | $3,324 2026 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
23330 Chestertown Rd |
3 ba · 2,504 sqft built 1968 · 1.9 acres | $120,000 Oct 1987 | $3,364 2026 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
23461 Chestertown Rd |
1.5 ba · 2,750 sqft built 1940 · 182 acres | $630,000 Feb 1979 | $3,419 2026 | Assessor Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
23548 Chestertown Rd |
104 acres | $35,590 Jun 2008 | $748 2026 | Assessor Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
23980 Chestertown Rd |
1.5 ba · 2,808 sqft built 1800 · 203 acres | — Aug 2000 | $5,284 2026 | Assessor Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24019 Chestertown Rd |
1 ba · 1,269 sqft built 1967 · 0.459 acres | $100,000 Sep 2022 | $2,208 2026 | Assessor + 4 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24025 Chestertown Rd |
1 ba · 1,408 sqft built 1965 · 0.459 acres | $142,000 Feb 2023 | $1,565 2026 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24039 Chestertown Rd |
2 ba · 1,248 sqft built 1970 · 0.459 acres | $214,000 Jan 2020 | $2,659 2026 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24055 Chestertown Rd |
1 ba · 1,000 sqft built 1969 · 0.459 acres | — Dec 1977 | $2,032 2026 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24065 Chestertown Rd |
1 ba · 1,204 sqft built 1968 · 0.459 acres | $140,000 May 2017 | $2,046 2026 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24075 Chestertown Rd |
1.5 ba · 1,356 sqft built 1962 · 0.459 acres | $114,000 Jul 1994 | $2,177 2026 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24085 Chestertown Rd |
1 ba · 1,248 sqft built 1973 · 0.459 acres | — Mar 1989 | $1,943 2026 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24095 Chestertown Rd |
1 ba · 1,104 sqft built 1972 · 0.459 acres | $310,000 Aug 2025 | $2,137 2026 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24105 Chestertown Rd |
1 ba · 1,317 sqft built 1970 · 0.459 acres | $275,000 Nov 2024 | $2,631 2026 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24115 Chestertown Rd |
1 ba · 1,143 sqft built 1960 · 0.459 acres | $110,000 Oct 2019 | $2,183 2026 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24133 Chestertown Rd |
2 ba · 4,221 sqft built 1967 · 0.905 acres | $90,000 Feb 2017 | $4,564 2026 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24153 Chestertown Rd |
1 ba · 1,968 sqft built 1973 · 0.965 acres | $58,500 May 1985 | $3,630 2026 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24219 Chestertown Rd |
1 ba · 1,050 sqft built 1973 · 0.682 acres | $223,000 Sep 2024 | $2,284 2026 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24231 Chestertown Rd |
1.5 ba · 1,152 sqft built 1964 · 0.443 acres | $95,000 May 1998 | $1,931 2026 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24239 Chestertown Rd |
1.5 ba · 1,246 sqft built 1964 · 0.454 acres | $60 2026 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24251 Chestertown Rd |
3.5 ba · 3,188 sqft built 1965 · 0.459 acres | $135,000 Dec 2015 | $3,186 2026 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24275 Chestertown Rd |
2 ba · 2,390 sqft built 1963 · 0.918 acres | — Dec 1998 | $60 2026 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24291 Chestertown Rd |
2 ba · 1,536 sqft built 1962 · 0.459 acres | $355,000 Dec 2024 | $2,868 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24301 Chestertown Rd |
1.5 ba · 1,120 sqft built 1977 · 0.459 acres | $124,000 Feb 2001 | $2,142 2026 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24311 Chestertown Rd |
2 ba · 1,400 sqft built 1961 · 0.459 acres | $120,000 Jul 2017 | $2,040 2026 | Assessor + 4 Documents Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24325 Chestertown Rd |
1.36 acres | $175,000 May 2013 | $454 2026 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24339 Chestertown Rd |
1 ba · 960 sqft built 1964 · 0.459 acres | $270,000 Feb 2026 | $1,809 2026 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24349 Chestertown Rd |
1 ba · 1,327 sqft built 1962 · 0.918 acres | $326,100 Jan 2024 | $3,200 2026 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24363 Chestertown Rd |
1.5 ba · 2,460 sqft built 1963 · 0.918 acres | $105,000 Jul 1991 | $2,976 2026 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24377 Chestertown Rd |
1 ba · 850 sqft built 1962 · 0.459 acres | $67,000 Nov 1999 | $1,826 2026 | Assessor Updated Sep 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24391 Chestertown Rd |
2 ba · 1,040 sqft built 1960 · 1.06 acres | $95,500 Feb 2017 | $2,158 2026 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24415 Chestertown Rd |
1 ba · 1,110 sqft built 1962 · 1 acre | $264,900 Nov 2025 | $2,196 2026 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24420 Chestertown Rd |
1.5 ba · 2,623 sqft built 1900 · 11 acres | — Mar 2006 | $4,171 2026 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24429 Chestertown Rd |
2 ba · 2,016 sqft built 1900 · 0.9 acres | $265,000 Mar 2021 | $3,311 2026 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24435 Chestertown Rd |
1 ba · 1,152 sqft built 1949 · 1 acre | $32,500 Jun 2013 | $2,245 2026 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24476 Chestertown Rd |
2 ba · 1,792 sqft built 1900 · 4.76 acres | — Oct 2006 | $2,917 2026 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24519 Chestertown Rd |
2 ba · 1,500 sqft built 2020 · 1.01 acres | $239,900 Sep 2020 | $2,763 2026 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24527 Chestertown Rd |
1.5 ba · 1,644 sqft built 1970 · 0.923 acres | $223,000 Jun 2005 | $2,825 2026 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24543 Chestertown Rd |
1.5 ba · 3,320 sqft built 1920 · 10 acres | $186,000 Jun 1998 | $4,335 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24589 Chestertown Rd |
1.5 ba · 2,224 sqft built 1961 · 0.815 acres | $192,500 Mar 2011 | $3,697 2026 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24593 Chestertown Rd |
2.5 ba · 2,201 sqft built 2020 · 0.8 acres | $400,000 Sep 2020 | $4,854 2026 | Assessor + 6 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24607 Chestertown Rd |
2.5 ba · 2,294 sqft built 1927 · 0.652 acres | $265,000 Aug 2021 | $3,609 2026 | Assessor + 4 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24625 Chestertown Rd |
1 ba · 1,048 sqft built 1920 · 2.13 acres | $144,000 Mar 2014 | $2,673 2026 | Assessor + 3 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24649 Chestertown Rd |
2 ba · 1,852 sqft built 1900 · 0.746 acres | $147,500 Mar 2007 | $4,052 2026 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24665 Chestertown Rd |
3.5 ba · 3,577 sqft built 1989 · 1.48 acres | $169,000 Jun 2013 | $4,354 2026 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24704 Chestertown Rd |
2.5 ba · 1,280 sqft built 2014 · 223 acres | — Dec 1998 | $6,167 2026 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24904 Chestertown Rd |
3.5 ba · 4,109 sqft built 2005 · 127 acres | $9,233 2026 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24913 Chestertown Rd |
2 ba · 3,943 sqft built 1900 · 233 acres | — Jun 2010 | $7,066 2026 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
25026 Chestertown Rd |
1 ba · 1,485 sqft built 1962 · 0.692 acres | $215,000 Aug 2020 | $2,817 2026 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
25030 Chestertown Rd |
2 ba · 1,260 sqft built 1955 · 0.513 acres | $213,000 Nov 2020 | $2,393 2026 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
25155 Chestertown Rd |
2 ba · 1,456 sqft built 1920 · 4.16 acres | $255,000 Jun 2017 | $2,942 2026 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
25227 Chestertown Rd |
7.5 ba · 6,123 sqft built 1800 · 20 acres | $2,195,000 Oct 2020 | $19,799 2026 | Assessor + 6 Documents Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
25325 Chestertown Rd |
1.5 ba · 1,941 sqft built 1920 · 1.58 acres | $74,000 Nov 1999 | $2,341 2026 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |