The Florida Midland Railway Company was incorporated under the general incorporation laws of Florida, and surveyed a line from Lake Jessup, in Orange County, to Leesburg, in Lake County.
The company was reincorporated on February 10, 1885; only 10 miles (16 km) had been graded. The new owners were E. W. Henck, S. M. Breuster, Carl Cushing, A. Menser and C. E. Munson of Florida, and Edward Page, Charles W. Morris and Cyrus Carpenter of Boston, Massachusetts.
The line was extended
Land grants were promised, as long as part of the railroad was completed within a year.
Florida state law chapter 3795, approved June 2, 1887, expanded the area from which land grants could be chosen, and extended the deadline to June 1, 1888.
The line actually built was rather different, running from Clifton on Lake Jesup west to Apopka, but then turning south to Kissimmee.
The railroad's track was 4 ft 8 1⁄2 in (1,435 mm) standard gauge while it was independent, but when it was taken over by the Plant System in the late 1890s, all track north of the 3 ft (914 mm) narrow gauge section of the Sanford and St. Petersburg Railroad (also taken over by the Plant System) was abandoned and the remaining trackage from Sanford to Kissimmee was converted to 3 ft narrow gauge. The two narrow gauge lines were run in conjunction with one another, allowing the usage of the same narrow gauge equipment on both lines. The Plant System became part of the Atlantic Coast Line Railroad system in 1902.