By the 1950s, NAS Sanford was being converted into a Master Jet Base for carrier-based heavy attack aircraft and, along with the re-designated Orlando Air Force Base and nearby Pinecastle AFB (later renamed McCoy AFB), saw even more military families renting or purchasing homes in and around Longwood.

Longwood Slade Airport[5] was located on the west side of the city on the north side of State Road 434 until it was closed and developed into tract housing that became The Woodlands subdivision in the late 1960s, its entrance road being named Slade Drive.

The development and opening of Walt Disney World in October 1971, along with other tourist attractions and the high technology corridor of businesses, especially those engaged in the modeling, simulation and training (MS&T) industry and associated military training systems activities near Florida Technological University (FTU), now the University of Central Florida (UCF), fueled even further growth.

By 2000, the city had taken significant steps to revitalize its downtown historic district, expanded its borders through annexation and in the process gained a resident population exceeding 13,700.

In 1965, the city served as a film site and backdrop, representing a fictional south Florida town adjacent to a Seminole Indian tribe reservation in the Universal Studios movie Johnny Tiger.