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 producer's in the state during the early 1900's and became known as the "Cucumber Capital".

Streets were paved, a central water supply system and elevated tanks were constructed, and a new railroad depot was built between 1925 and 1929.

The Sumter County Farmers' Market was the result of a group of area farmers organizing a co-op in which they could sell their farm products.  The farmer's Market was organized in 1938.  Livestock sales are held each week along with the sale of vegetables.  A "flea market" began, along with the sale of the farm products and has become one of the largest of the flea markets in Florida.  Today it has a Main and a West Side section. 

 

      The Climate for Webster, is considered subtropical with warm, humid summers and mild, relatively dry winters.  The nearest climate data recording station is located in Bushnell.

The mean annual temperature is 71 degrees.   The annual average precipitation is approximately 54 inches with approximately 56% of the rainfall occurring during the four month period, June through September.