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
... beginning at a point on the Indian River and running through the counties of Brevard and Orange to Leesburg, in Sumter county, or to Eustis, in Orange county, or to points or a point of connection with railroads or a railroad running from these places, or from either of them, and from a point on the line of said road, in Orange county, to a point on the Gulf of Mexico, running through the counties of Orange, Sumter, Polk, Hernando, Hillsborough, Manatee and Monroe, or such of them as may be necessary to reach the terminal point, which shall be selected on the Gulf of Mexico.
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.