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Major cities near Leesburg, FL. This is a list of large cities closest to Leesburg, FL. A big city usually has a population of at least 200,000 and you can often fly into a major airport. If you need to book a flight, search for the nearest airport to Leesburg, FL. 36 miles to Orlando, FL; 69 miles to Tampa, FL; 87 miles to Saint Petersburg, FL
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