The history of SR 408 and the Expressway Authority is closely tied to the history of the growth of Central Florida. The Expressway Authority was established by the state Legislature in 1963 primarily to build the SR 528 Bee Line Expressway (now the BeachLine Expressway).
In early 1966 when the Expressway Authority was building SR 528, then-Governor Haydon Burns asked the agency to look into an east-west freeway through downtown Orlando to relieve traffic on SR 50. At the time SR 50 was the only east-west road across town, and the expected openings of the Naval Training Center in 1968, the Florida Technological University (now UCF) in 1969 and Walt Disney’s huge theme park in 1971 raised concerns that Colonial Drive traffic would become gridlocked.
After extensive planning and public debate the final design took SR 408 across Interstate 4 just south of Anderson Street, through town and across Lake Underhill. The $89 million expressway opened in 1973 from SR 50 just east of what’s now Hiawassee Road, heading south and through downtown and across Lake Underhill, and then back north to SR 50 east of Goldenrod Road.
The road was formally dedicated the Spessard Lindsay Holland East-West Expressway in honor of the popular four-term United States Senator from Lakeland, who had just retired from office.
The new road included two new mainline toll plazas (Holland West and Holland East) and ramp toll plazas at U.S. Highway 441 (Orange Blossom Trail), Mills Avenue, Bumby Avenue, Conway Road and SR 436 (Semoran Boulevard). Drivers initially were charged 20 cents at the main toll plazas and 10 cents at the ramp exits.
By 1984, the alignment of the SR 408 eastern extension had been chosen. Construction began in 1987, and the section from existing SR 408 to Rouse Road opened in May 1989. The rest of the six-mile road opened in June 1989, at a total cost of $105 million. This project included a full interchange with the planned SR 417’s Southeastern Beltway (opened in April 1990), the new Dean Road Main Toll Plaza, as well as a connection at the east end at SR 50 to the Central Florida Research Park.
An initial connection to Florida's Turnpike and the planned SR 429 (then-Western Beltway) was studied in 1985 and approved by the Expressway Authority Board in July 1986. Construction of the 4.5-mile extension began in mid-1989 and was completed on October 8, 1990 at a cost of $102 million. This project included adding the Hiawassee Main Toll Plaza. The full interchange with the Turnpike was completed in August 2006.
Also in 2006, the Expressway Authority finished building two new access ramps to connect Good Homes Road with SR 408 in both directions. Additionally, the Expressway Authority widened the Good Homes Road bridge to accommodate Orange County’s project to widen that side street between SR 50 and Old Winter Garden Road.
In the summer of 2010, the SR 408 widening and improvements continued with new projects between Goldenrod Road and the SR 417 Interchange. Work on those projects was completed in January 2013 with the final completion of the SR 408/SR 417 North Interchange Project and the opening of the SR 408/Chickasaw Trail Half Interchange Project which also featured a connector road to Valencia College Lane.