Touring Historic Longwood, Florida


After the Second Seminole War ended homesteads were granted in 1870 and a community south of Sanford began. Settler Edward Henck of Boston named Longwood after one of his hometown’s most attractive suburbs and in 1876 he founded the first post office and became the first postmaster.

1880 saw the first railroad constructed from Sanford to Orlando. The Longwood Hotel was constructed and Henck became the very first mayor. (Are you surprised? I can’t believe it’s not called Henckville.)

The Longwood Hotel, built in 1886, has operated under a number of aliases. Originally The Waltham, it was changed to St. George, the the Orange and Black and then became the Longwood Hotel. In 1925 the owner George Clark died in the building and some say he haunts it. Workers hear giggles of children and tapping on walls. As the Orange and Black it was a sporting establishment. In the 1950s it was an umpire school and in the 1970s it was used by Cornell University to teach hotel operations.

By 1886 there were over 1,000 people living in Longwood. The area was a booming community and one of the largest in Orange County. Seminole County wasn’t founded until 1913. It’s now the oldest city in Seminole County.

Fun Fact: P.A. Demens arrived from Russia in 1881 and bought a sawmill. He did quite well and eventually founded the Orange Belt Railroad that took the train line from Sanford to Tampa Bay. Know what he named the terminus? St. Petersburg, after his hometown in Russia. Yep. There ya go, Gulf Coast fam.

In 1894, the Great Freeze knocked out the citrus farms and by 1900 only 324 people remained. Time crept on and by the 1920s real estate was booming. In 1923 Longwood was incorporated as a city and got it’s own Dixie Highway, also known as County Road 427.

In 1920 Henck and baseball great Joe Tinker build the Henck-Tinker building that still remains across the street from the Longwood Hotel. It housed the first bank, MacReynold’s Drugstore, Jackson’s Grocery, and a barbershop. The building angled toward the road and while it sat adjacent to the train depot, it didn’t face that way. It faced toward the automobiles and the town. Really signifying the change in thinking about transportation. The bank went under during the Depression, but the vault remains.

The 30s and 40s underwent another period of stalled expansion and then in the 70s and 80s, Longwood became a comfortable residential community. By 2000, the population had risen to 13,000.

Here’s a great little walking map of the area if you venture there.

Looking for a place to sit and chill?

Zanzibar Coffee

315 N Ronald Reagan Blvd.
Longwood, FL 32750
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