While Lee became the area’s first permanent settler, Thomas Robertson and his 21-year-old son, John Marmaduke Robertson came to what would become Leesburg in 1843, or likely a year sooner. They lived in what would become the heart of Leesburg for 11 years before Thomas sold out and moved back to Moss Bluff. John later sold his property and founded the nearby community of Whitney.
Evander Lee moved to the area in 1857, a year after his father died. They had moved to Adamsville from Alabama in 1849. Evander Lee brought with him his wife Susan and eight children. He purchased the old Thomas Robertson homestead from James Fussell for $3,300. Several Lee brothers also joined Evander, and his brother, Calvin Lee, is credited with giving Leesburg its name. Calvin and Evander had built a log store on Main Street where the public restroom is now located. When Calvin went on a buying trip to New York City and was asked where to ship the merchandise, he reportedly told his suppliers to bill his goods to "Leesburg."
Here are a few important dates in Leesburg history:
- July 12, 1875 - The city was incorporated about a dozen years before Lake County was formed from portions of Sumter and Orange counties.
- 1922 - The city changed its form of government when the new City Charter established a City Commission.
- 1926 - The present City Hall was built.
- 1930 - The first Watermelon Festival was held.
- 1938 - Work on Venetian Gardens was started as a Works Progress Administration (WPA) project.