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.
- You can sort the table in an ascending or descending order by clicking on the title of each column.
- To see a photo of an individual mayor, simply click on the camera icon.
| Order |
Years |
Name |
Photo |
| 1 |
1887 - 1890 |
Robert White |
. |
| 2 |
1890 - 1893 |
Henry S. Chubb |
 |
| 3 |
1893 - 1895 |
Dr. M.A. Henkel |
|
| 4 |
1895 - 1896 |
George D. Rand |
. |
| 5 |
1896 - 1898 |
L.A. Austin |
. |
| 6 |
1898 - 1899 |
A.E. Rogers |
. |
| 7 |
1899 - 1901 |
A. Richmond |
. |
| 8 |
1901 - 1903 |
S.P. Shepherd |
. |
| 9 |
1903 - 1904 |
F.V. Phillips |
. |
| 10 |
1904 - 1905 |
G.W. Van Sickle |
. |
| 11 |
1905 - 1906 |
Dr. W.F. Blackman |
|
| 12 |
1906 - 1908 |
Dr. M.A. Henkel |
|
| 13 |
1908 - 1909 |
Henry S. Chubb Jr. |
. |
| 14 |
1909 - 1910 |
Girard Denning |
|
| 15 |
1910 - 1911 |
William C. Temple |
|
| 16 |
1911 - 1912 |
Phillip Dale |
. |
| 17 |
1912 - 1913 |
Thomas Henkel |
|
| 18 |
1913 - 1914 |
William C. Temple |
|
| 19 |
1914 - 1915 |
Phillip Dale |
. |
| 20 |
1915 - 1917 |
William C. Temple |
|
| 21 |
1917 - 1918 |
Thomas R. Baker |
. |
| 22 |
1918 - 1920 |
William H. Shultz |
. |
| 23 |
1920 - 1921 |
Harley A. Ward |
|
| 24 |
1921 - 1922 |
Edward F. Keezel |
|
| 25 |
1922 - 1924 |
James A. Treat |
|
| 26 |
1924 - 1928 |
C. Fred Ward |
|
| 27 |
1928 - 1933 |
F.W. Cady |
|
| 28 |
1933 - 1935 |
James A. Treat |
|
| 29 |
1935 - 1937 |
Raymond C. Baker |
|
| 30 |
1937 - 1943 |
J.F. Moody |
|
| 31 |
1943 - 1945 |
Raymond C. Baker |
|
| 32 |
1945 - 1947 |
Herbert Halverstadt |
|
| 33 |
1947 - 1950 |
B.R. Coleman |
|
| 34 |
1950 |
Herb W. Barnum |
|
| 35 |
1950 - 1951 |
Carter Bradford |
|
| 36 |
1951 - 1952 |
William McCauley |
|
| 37 |
1952 |
Oliver K. Eaton |
|
| 38 |
1952 |
R.E. Carrigan |
. |
| 39 |
1952 |
James A. Keezel |
|
| 40 |
1952 - 1958 |
Raymond Greene |
|
| 41 |
1958 - 1961 |
J.L.Pflug |
|
| 42 |
1961 - 1962 |
Edward J. Gurney |
|
| 43 |
1962 - 1967 |
Allen Trovillion |
|
| 44 |
1967 - 1972 |
Daniel Hunter |
|
| 45 |
1972 - 1981 |
James A. Driver |
|
| 46 |
1981 - 1987 |
Hope Strong Jr. |
|
| 47 |
1987 - 1993 |
David Johnston |
|
| 48 |
1993 - 1997 |
Gary Brewer |
|
| 49 |
1997 - 2000 |
Joseph Terranova |
|
| 50 |
2000 - 2003 |
Roland “Terry” Hotard |
|
| 51 |
2003 - 2006 |
Kenneth “Kip” Marchman |
|
| 52 |
2006 - 2009 |
David Strong |
|
| 53 |
2009 - |
Ken Bradley |
|
|
