Mayors
The first election in the newly incorporated town of Winter Park took place on October 12, 1887. The election was held on the second floor of Ergood's Store, and a total of 71 votes were cast. Robert White, Jr. was elected Mayor. Since then, 51 other men have held this position. Here is a comprehensive list of the names of these men and the years they were in office.
This article was written by former archivist, Barbara White, MLIS.
| 1887 - 1890 | Robert White |
| 1890 - 1893 | Henry S. Chubb |
| 1893 - 1895 | Dr. M.A. Henkel |
| 1895 - 1896 | George D. Rand |
| 1896 - 1898 | L.A. Austin |
| 1898 - 1899 | A.E. Rogers |
| 1899 - 1901 | A. Richmond |
| 1901 - 1903 | S.P. Shepherd |
| 1903 - 1904 | F.V. Phillips |
| 1904 - 1905 | G.W. Van Sickle |
| 1905 - 1906 | Dr. W.F. Blackman |
| 1906 - 1908 | Dr. M.A. Henkel |
| 1908 - 1909 | Henry S. Chubb Jr. |
| 1909 - 1910 | Girard Denning |
| 1910 - 1911 | William C. Temple |
| 1911 - 1912 | Phillip Dale |
| 1912 - 1913 | Thomas Henkel |
| 1913 - 1914 | William C. Temple |
| 1914 - 1915 | Phillip Dale |
| 1915 - 1917 | William C. Temple |
| 1917 - 1918 | Thomas R. Baker |
| 1918 - 1920 | William H. Shultz |
| 1920 - 1921 | Harley A. Ward |
| 1921 - 1922 | Edward F. Keezel |
| 1922 - 1924 | James A. Treat |
| 1924 - 1928 | C. Fred Ward |
| 1928 - 1933 | F.W. Cady |
| 1933 - 1935 | James A. Treat |
| 1935 - 1937 | Raymond C. Baker |
| 1937 - 1943 | J.F. Moody |
| 1943 - 1945 | Raymond C. Baker |
| 1945 - 1947 | Herbert Halverstadt |
| 1947 - 1950 | B.R. Coleman |
| 1950 | Herb W. Barnum |
| 1950 - 1951 | Carter Bradford |
| 1951 - 1952 | William McCauley |
| 1952 | Oliver K. Eaton |
| 1952 | R.E. Carrigan |
| 1952 | James A. Keezel |
| 1952 - 1958 | Raymond Greene |
| 1958 - 1961 | J.L. Pflug |
| 1961 - 1962 | Edward J. Gurney |
| 1962 - 1967 | Allen Trovillion |
| 1967 - 1972 | Daniel Hunter |
| 1972 - 1981 | James A. Driver |
| 1981 - 1987 | Hope Strong Jr. |
| 1987 - 1993 | David Johnston |
| 1993 - 1997 | Gary Brewer |
| 1997 - 2000 | Joseph Terranova |
| 2000 - 2003 | Roland “Terry” Hotard |
| 2003 - 2006 | Kenneth “Kip” Marchman |
| 2006 - 2009 | David Strong |
| 2009 - 2015 | Kenneth Bradley |
| 2015 - 2021 | Steven Leary |
| 2021 - TBD | Phil Anderson |
