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.

[9] Regardless of their tribal identity, these natives were either wiped out or subsumed into larger cultures by the end of the eighteenth century.

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".

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.

[3] The arrival of the Orange Belt Railroad and the growing production of citrus, turpentine, and lumber drove the town's growth over the remaining decades of the 19th century and into the 20th.

[15] The still-operating Edgewater Hotel in Downtown Winter Garden opened to service fishermen during the fishing boom.

[16] Citrus agriculture saw rapid growth in the state of Florida in the last few decades of the 19th century, including in Winter Garden.

As with the rest of the state, the Great Freeze of 1894–1895 severely damaged the citrus industry in Winter Garden.

[20] Developers, entrepreneurs, and city government made efforts to rejuvenate the downtown district, attracting locals and tourists with a mix of small-town atmosphere and trendy businesses.

The area's warm and humid climate is caused primarily by its low elevation and its position relatively close to the Tropic of Cancer, and much of its weather is affected by the movement of the Gulf Stream.

The Winter Garden Downtown Historic District contains a collection of restaurants, shops, and cafés, as well as two museums and a performing arts venue.

The 1,100,000 square feet (100,000 m2) open-air shopping center, located along Daniels Road just north of SR 429, is anchored by a Super Target, a Best Buy, and a Lowe's.

Many vendors sell fresh produce, plants, and flowers, herbs, baked goods, artisan crafts, and local food and beverages.

The toll road Western Beltway (SR 429) was completed in late 2006 and links I-4 near mile marker 58 in Osceola County with Florida's Turnpike at Winter Garden.

CR 545 (also called Avalon Road) begins at SR 50 and proceeds south along the western edge of Winter Garden and along the border between Orange and Lake counties.