| 1777-1814 | Joseph Richardson |
| 1814-1822 | John Young |
| 1822-1825 | George A. Smith |
| 1825-1832 | James Langston |
| 1832-1851 | William A. Ford |
| 1851-1852 | John R. K. Horney |
| 1852-1853 | Henry C. Rawlings |
| 1853-1859 | William G. Nicholson |
| 1859-1865 | George H. Moore |
| 1865-1867 | Robert H. Todd |
| 1867-1873 | William Lockerman |
| 1873-1896 | James B. Steele |
| 1896-1912 | Robert J. Jump |
| 1912-1919 | Z. Potter Steele |
| 1919-1923 | John Howard Pastorfield |
| 1923 | Margaret Pastorfield |
| 1923-1930 | J. Irwin Harwood |
| 1930-1938 | John H. Carroll |
| 1938-1962 | Carlton V. West |
| 1962-1978 | Clifford L. Stafford |
| 1978-1994 | Charles V. Moore |
| 1994-2010 | Charles O. Davis, Jr. |
| 2010-2024 | James L. Phelps |
| 2024-present | Linda A. Dunn |
Sources:
CAROLINE COUNTY REGISTER OF WILLS (Orphans Court Proceedings) MSA C545
and T1267
GOVERNOR AND COUNCIL (Commission Record) MSA S1080
Maryland Manual
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