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The pre-European history of the modern Winter Garden area is ambiguous. Due to a lack of evidence, historians hesitate to conclude if the natives that once occupied the area were of the Timucua, Jororo, or Mayaca tribes. Regardless of their tribal identity, these natives were either wiped out or subsumed into larger cultures by the end of the eighteenth century.

Following the eradication of the original Floridian cultures, natives from farther north migrated into Florida. These natives had various cultures that over time coalesced into the Seminole Tribe. By the early 19th century, some Seminole lived on the south shore of Lake Apopka. The settlement possibly produced the significant Seminole leader Wild Cat. In 1835, the Second Seminole War began, threatening the Seminole presence. On January 23, 1837, a small battle was fought near the village. Thomas S. Jesup, at that time in command of all American forces in Florida, sent a detachment to Lake Apopka to seek a Seminole chief known as Osuchee or “Copper.” During the attack, the army successfully killed Osuchee and three other Seminoles, while taking 17 prisoners. The Second and Third Seminole wars both pushed the Seminole tribe south, likely eliminating their presence in the boundaries of modern Winter Garden.

The first American settlers came to what is now Winter Garden in the 1850s. The Roper, Reams, Dunaway, Speer, and Starke families were among the first to settle the area. As with most American pioneers, they engaged in agriculture as a primary economic activity. These farms mainly grew sugar cane and vegetables, and early on a small number utilized slave labor. During The Civil War steamboat traffic stopped along the St. Johns River, forcing Winter Garden families to subsist off their own crops.