Leesburg is a city in Lake County, Florida, United States. The population was 20,117 at the 2010 census. As of 2019, the population recorded by the U.S. Census Bureau was 23,671.

Leesburg is in central Florida, between Lake Harris and Lake Griffin, at the head of the Ocklawaha River system. It is part of the Orlando–Kissimmee–Sanford Metropolitan Statistical Area. It is about 45 miles NW of Orlando, 270 Miles N of Miami, and 221 Miles SW of the State Capitol at Tallahassee.

Leesburg is the home of Lake–Sumter State College (LSSC), which also has campuses in Clermont and Sumterville, Florida. It is also the home of Beacon College.

Leesburg was first settled in 1857 by Evander McIver Lee. Several of his brothers followed him to the area. One of them, Calvin Lee, was credited with giving the town its name. The city was incorporated in 1875, and was designated as the county seat of Sumter County for a time. When Lake County was formed in 1887, Tavares was designated as its seat.

In the early 20th century, Leesburg was an important center for watermelon production. In 1930, it held its first Watermelon Festival, an annual tradition that lasted for nearly 30 years. But gradually watermelon production dwindled and, for the last festival in 1957, watermelons had to be brought to the city from outside the area.

Lake Square Mall, the city’s major shopping mall, opened in 1980. On March 19, 1982, Ozzy Osbourne’s guitarist Randy Rhoads, as well as the band’s cook and bus driver, were killed in a plane crash at Flying Baron Estates.

The citrus industry was the principal business in this area for decades, but devastating freezes in December 1983 and February 1985 persuaded growers to move their groves further south. In 1997, Leesburg Bikefest started. It has since become an annual spring tradition, with upwards of 250,000 people attending every year. Today, most of Leesburg’s growth and economic development is the result of its increasing popularity as a retirement destination. In addition, the rapid growth of nearby Orlando has resulted in demand for housing here, as many people commute to Orlando for work. In 2011 and 2017, the Leesburg High School boys’ basketball team won the 4A state championship.