The Timucuan Indians once lived in the vicinity of Lake Monroe, where the domain of Chief Utina extended to just north of Lake George. They hunted, fished and gathered plants and berries from the forest. By 1760, however, the Timucua had disappeared and been replaced by the Seminole tribe from Alabama and Georgia. Florida was acquired from Spain in 1821, but the Seminole Wars would delay settlement. In 1866, Elijah Watson of Enterprise sold land to Oliver and Amanda Arnett on the northern shore of the St. Johns River at Lake Monroe, where they built a house.

The couple in turn sold 400 acres (1.6 km²) in 1871 to (Samuel) Frederick deBary, a wealthy wine merchant from New York City, and that same year he erected a hunting lodge. Called "DeBary Hall," the 8,000 square foot (700 m²), 20 room Italianate mansion featured a two-tiered veranda, stables, an ice-house and the state's first swimming pool, fed by a spring. Visitors included President Ulysses S. Grant and President Grover Cleveland. Over time he acquired an additional 9,000 acres (36 km²), planting orange groves and pecan trees. There is some debate as to whether this was actually the first pool in Florida, as a St. Augustine pool has also made the same claim. One possibility is that this was the first Spring-fed pool in the state (See Orlando Sentinel article).

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