Longwood, Florida boasts a charming history nestled within the Orlando metropolitan area. The area’s indigenous inhabitants date back thousands of years, but American settlement began in the 1870s after the Second Seminole War. John Neill Searcy and Edward Warren Henck are recognized as some of the first documented settlers, arriving by steamboat and establishing homesteads in the region.

By the mid-1920s, Longwood officially incorporated as a city, fueled by the Florida land boom. The historic district still showcases remnants of this era, with buildings like the Longwood Village Inn, which once hosted governors’ conferences, and the Queen Anne-style Bradlee-McIntyre House, a testament to the area’s architectural heritage.

Longwood Historic District

16,842 (2022)