Webster was first settled during 1855, making it the oldest incorporated town in Sumter County. In 1870, when the residents of the Webster area applied for a post office, the name of Orange Home was submitted. Since there was already a town named Orange Home, the application was rejected. Upon receiving the notice of rejection from the Postal service, the postmaster picked up a Webster’s dictionary and decided to call the town “Webster” Webster has currently two public schools, Webster Elementary, and South Sumter Middle School. Originally in 1912 there were two other schools … Webster High School and Mills High School. Before integration, these were the two High Schools in Webster which were later converted to a single Middle School (the South Sumter Middle School), with the High School components being merged into the High School in Bushnell. This High School merger was then named South Sumter High School. The Economy of Webster was based on the Citrus industry until the great freeze of 1894-95. This freeze destroyed large portions of the orange groves in Central Florida, including those in Webster. Soon after the freeze, Webster suffered a loss in population. Naval stores replaced the Citrus industry for a time, but soon failed. The growing and marketing of vegetables became Webster’s main economic base, and Webster began to grow once more. The Webster area became one of the largest vegetable producers in the state during the early 1900’s and became known as the “Cucumber Capital”. Webster is home to The Webster Flea Market, the largest farmer’s market in the country as well as one of the last surviving Cattle Markets in the country.
Webster Real Estate Market