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Webster is a small city in Sumter County, Florida, in the gently rolling countryside of the state's central interior, southwest of The Villages and northwest of the Withlacoochee State Forest. Settled in 1855, it is the oldest incorporated town in Sumter County, with a history built on vegetable farming and cattle ranching. The town's name honors the statesman Daniel Webster, and for generations its identity has been tied to the surrounding fields and pastures that still blanket the area. What has put Webster on the map for modern visitors, however, is its market culture. Local farmers organized a cooperative in 1938 that became the Sumter County Farmers Market, a community anchor for the region's produce trade. More famously, the Webster Westside Flea Market — better known as the Swap-O-Rama — operates every Monday across 35 acres and is billed as Florida's largest weekly flea market, drawing thousands of vendors and shoppers from across the state. That single day each week gives this otherwise quiet town a distinctive commercial energy. With roughly 1,000 residents, Webster remains a small, close-knit place where most people know one another and life follows the slower rhythms of a farm community. The Sumter County School District serves local students, with Webster Elementary School in town and middle and high school campuses in the surrounding area. The Withlacoochee State Forest borders the community, providing hiking, biking, horseback riding, camping, and access to the 46-mile Withlacoochee State Trail. For residents, Webster offers a rural, lower-density alternative to Florida's sprawling retirement and suburban developments. It combines a genuine agricultural character, a landmark weekly market, and easy access to the outdoor recreation of the state forest, all within reach of The Villages and the region's growing services. It is a place for those who value space, simplicity, and country living over the pace of central Florida's larger communities.

Population 1,029

County Sumter County

Active Listings 323

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Frequently Asked Questions

What county is Webster in?

Webster is in Sumter County, Florida, in the central part of the state southwest of The Villages. It was settled in 1855 and is the oldest incorporated town in the county.

What is Webster known for?

The Webster Westside Flea Market, also known as the Swap-O-Rama, is billed as Florida's largest weekly flea market. It is held every Monday across 35 acres and has operated for more than 50 years, drawing vendors and shoppers from across the region.

What school district serves Webster?

Webster is served by the Sumter County School District. Webster Elementary School is located in town, while students attend middle and high school campuses in the surrounding Sumter County area, including South Sumter schools.

What outdoor recreation is near Webster?

The Withlacoochee State Forest surrounds much of the Webster area, offering hiking, biking, horseback riding, and camping, including the River Junction Campground. The 46-mile Withlacoochee State Trail runs through the countryside nearby.

What is Webster's economy like?

Webster's economy is rooted in farming. Vegetable and cattle operations blanket the area, and local farmers organized a co-op in 1938 that became the Sumter County Farmers Market. The weekly flea market and proximity to The Villages add commercial activity.

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