| 1812-1812 | William H. Johnston |
| 1813-1814 | Peter Crosby |
| 1815-1818 | Peter Warren |
| 1819-1820 | Edward Buckbee |
| 1821-1821 | Joseph Cole |
| 1822-1823 | Edward Buckbee |
| 1823-1825 | Edward Buckbee |
| 1826-1828 | Thomas W. Taylor |
| 1829-1831 | Joseph Cole II |
| 1832-1834 | Nathaniel Cole |
| 1835-1837 | Thomas W. Taylor |
| 1838-1840 | George W. Travis |
| 1841-1843 | William W. Taylor - Son of Thomas W. Taylor |
| 1844-1846 | James Smith |
| 1847-1849 | William W. Taylor |
| 1849-1850 | Sheriff Taylor died in office in March of 1849, Joseph E.M. Hobby was appointed to finish the term. |
| 1850-1852 | James J. Smalley |
| 1853-1855 | Harvey Mead |
| 1856-1858 | Charles T. Brewster |
| 1859-1861 | Daniel B. Lockwood |
| 1862-1864 | Charles T. Brewster |
| 1865-1867 | John J. Smalley - Son of Sheriff James J. Smalley |
| 1868-1870 | John Butler |
| 1871-1873 | Richard R. Horton |
| 1874-1876 | James O. Cole - Son of Sheriff Nathaniel Cole and the nephew of Sheriff Joseph Cole |
| 1877-1879 | Edmund Doane |
| 1180–1882 | James O. Cole |
| 1883-1883 | James J. Dakin |
| 1884-1886 | Jeremiah W. Hazen |
| 1887-1888 | James O. Cole |
| 1888-1889 | Sheriff Cole died in office in May of 1888, Lewis E. Cole was appointed to finish the term. |
| 1889-1891 | William E. Nelson |
| 1891-1892 | Sheriff Nelson died in office in February of 1891, James E. Warner was appointed to finish the term. |
| 1892-1894 | Reuben R. Barrett |
| 1895-1897 | Jeremiah W. Hazen |
| 1898-1900 | John P. Donohoe |
| 1901-1903 | Jeremiah W. Hazen |
| 1904-1906 | Leonard Jaycox |
| 1907-1909 | Joseph Barry |
| 1910-1912 | Charles E. Nichols |
| 1913-1915 | Herbert Winship |
| 1916-1918 | Charles E. Nichols |
| 1919-1921 | Henry B. Stephens |
| 1922-1924 | Wallace Secord |
| 1925-1927 | Henry B. Stephens |
| 1928-1930 | Wallace Secord |
| 1931-1933 | Arthur L. Newcomb |
| 1934-1936 | Leander Currey |
| 1937-1939 | Allen G. N. Gilbert |
| 1940-1942 | Percy L. Barker |
| 1943-1945 | Allen G. N. Gilbert |
| 1946-1948 | B. Scofield Palmer |
| 1948-1966 | Frank Lyden |
| 1967-1985 | Raynor Weizenecker |
| 1985-1986 | George A. Grenier |
| 1986-2001 | Robert D. Thoubboron |
| 2002-2017 | Donald B. Smith |
| 2018-2021 | Robert L. Langley Jr. |
| 2021-2025 | Kevin McConville |
| Current | Brian M. Hess |
