Located south of Sanford and west of Winter Springs, the city of Longwood was first settled in the 1870s. Edward Warren "E.W." Henck, a native of Boston, was among the first to settle in the area. He was a railroad and hotel owner, as well as a real estate promoter. Henck served as the first postmaster at Longwood's first post office in 1876.

Henck named the city Longwood after a suburb in Boston he helped design which is now known as Brookline. He became the town's first mayor in 1885. By 1895, thanks to Henck's relentless promotions, Longwood expanded and now boasted five churches, three hotels, eight stores and a weekly newspaper. The citrus industry was responsible for most of this prosperity, so when hit by the freezes of 1895 and 1896 many businesses abandoned the town, which continued to decline until the mid-1920s.

Another boom, influenced by the construction of the Dixie Highway, ended due to the Great Depression. Following World War II and then the arrival of Walt Disney World, Longwood became the residential community it is today. The history of the city of Longwood shows the ingenuity and hard work of the early settlers and founders of the city.

Submitted by K. Malcolm, University of Central Florida