Jefferson County, named in honor of Thomas Jefferson, the third president of the United States, was established in 1827. The county seat, Monticello, named after Jefferson’s Virginia home, still remains the county's only incorporated city. During the 1830's the county began to suffer, as residents went off to fight in the Seminole Wars. Twenty years later the railroad ventured through the county making a train stop at Station Number Two which brought into existence, the town of Lloyd. The railroads were to thank for the early prosperity of Aucilla, Lloyd and Wacissa, however, Monticella was located three miles to the north. With the economic struggles of the railroad debt, the Civil War and the suffering cotton crops the settlers in the area began to seek out other locations to settle down. It was not until the 1880's, when William Cirardeau sent out the first shipment of watermelon seeds, and nearly 40 years later, Jefferson County was responsible for 80% of the world's watermelon supply! Unlike most other Florida counties, Jefferson County devoted its time to agriculture instead of the tourist trade.

Today Jefferson County is home to cities such as Capps, Drifton, Lamont, Lloyd, Monticello and Wacissa. In honor of the watermelon, that set Jefferson County back on it's feet financially, so many years ago, the Watermelon Festival is held annually in June. The festival includes street dances, beauty pageants, The Water Melon Crawl, bed races, food vendors, parades and lots and lots of Watermelons! Located on the beautiful Gulf of Mexico provides access to some of the most pristine boating, fishing, swimming, sunset gazing and water recreation. The small and relaxing county of Jefferson stretches from Georgia to the Gulf of Mexico and in right dab in the middle of Tallahassee, Florida and Thomasville, Georgia. This location provides residents in the area the convenience of all the small town charm that the cities of Jefferson County have to offer, mixed with big city life advantages only a few miles away!

Relocating to Jefferson County can provide miles of pastoral countryside as well as three major rivers that flow freely through the county; the Wacissa, Aucilla and St. Marks. These rivers combined with the Gulf of Mexico makes the opportunities for owning waterfront property within reach. Whether you are seeking for a place to retire or raise a family, Jefferson County has a little something for everyone.