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Mr. E.W. Henck, a young man from Boston, arrived in this wilderness section of then Orange County in November 1872. He selected a site to homestead in what is now Historic Longwood. Intent on establishing a town, he named it Longwood after a beautiful Boston suburb (now Brookline) that he helped lay out as a young engineer. At that time the Hartley family had a homestead southeast of Henck's. The Searcy family and the Rand family were other early residents of the area.
Mr. Henck platted the town, became the first postmaster in 1876, and in 1879, along with Mr. Haskell and Mr. Rand, obtained a charter for the railroad between Sanford and Orlando. The railroad was completed in 1880 with a station in Longwood. The village grew rapidly with the building of the railroad, with the establishment of a large sawmill owned by Capt. Peter Demens, orange groves, and the arrival of winter visitors. In 1883 Longwood was incorporated as a town with Mr. Henck becoming the first mayor.
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By 1887 the population of Longwood had grown to 1,027. The town had 3 hotels, 5 churches, 8 stores and a weekly newspaper. The killing freezes of 1895 and 1896 devastated the orange business. This together with the depletion of the nearby native forests greatly reduced Longwood's population.
The Florida land boom of the early 1920's again saw a revival of Longwood with the paving of many streets, a municipal water system, and in 1923, its re-incorporation as a city. In nearby areas attractions were built that included a dog track, a horse track, and a golf course. The boom fizzled and the depression of the 1930's left the Longwood population much as it was before the boom started.
The population growth of central Florida in the later part of the 20th century began Longwood's expansion outside of the historic district. The area platted by Mr. Henck became Longwood's Historic District and is listed on the National Register of Historic Places.