In 1938, during the Great Depression, the Franklin D. Roosevelt administration invested in infrastructure and improvement projects across the county.

On March 19, 1982, Ozzy Osbourne's guitarist Randy Rhoads, as well as the band's makeup artist and bus driver, were killed in a plane crash at Flying Baron Estates.

[5] 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.

Today, most of Leesburg's growth and economic development is the result of its increasing popularity as a retirement destination.

In spring 2017, the Holding Company of the Villages planned to acquire 2,600 acres north and south of County Road 470 along the east side of Florida’s Turnpike for future development.

The deal with the mega-retirement community has passed due diligence by the Leesburg City Commission.

[6] The initial plans call for building approximately 4,500 homes and some commercial development.

The climate in this area is characterized by hot, humid summers and generally mild winters.

As of the 2020 United States census, there were 27,000 people, 9,142 households, and 5,782 families residing in the city.

[14] As of the 2010 United States census, there were 20,117 people, 8,684 households, and 5,144 families residing in the city.

[21] From 1922 to 1924, the city's Cooke Field was used by the Philadelphia Phillies for their spring training sessions.

[22] On March 14, 1923, the stadium was used for the site of an exhibition game between the Phillies and the St. Louis Cardinals.

During the 1920s, sharpshooter Annie Oakley, who had a residence in Leesburg, performed shooting exhibitions at Cooke Field, including one for the Philadelphia Phillies.

[25] Lake County Schools operates public primary and secondary schools: Leesburg International Airport is a small hub airport at the intersection of CR 44 and US 441, in front of Lake-Sumter State College.