Monticello, Florida: A Historic Small-Town Charm with Southern Soul Monticello is part of Jefferson County, and the heart of “Natural North Florida.” It is located just 25 miles east of Tallahassee, making it a popular option for people who work and/or go to school in Tallahassee. The historic district features limestone streets, Victorian homes, and classical architecture. Monticello is also a destination for Tallahassee residents for their community events they host throughout the year.