Winter Garden is a city in western Orange County, Florida, United States. Located 14 miles (23 km) west of Downtown Orlando, it is part of the Orlando metropolitan area. The population was 46,964 as of the 2020 census.

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.

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. Stores and businesses cropped up along Plant Street, originating Downtown Winter Garden. A settler from Mississippi named A. B. Newton contributed to the town's early economy. He opened one of the first stores, served as the first postmaster, founded the first newspaper, and functioned as the first mayor. These endeavors earned him the title "The Godfather of Winter Garden".

Between the 1920s and 1960s, the fishing prospects of Lake Apopka drew many fishermen to Winter Garden. The Edgewater Hotel in Downtown Winter Garden opened to service fishermen during the fishing boom. However, by the end of the 1960s, heavy pollution of Lake Apopka resulted in the collapse of the industry.

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. Many settlers left following this disaster, leaving a smaller population to recover the area's farms. Despite this setback, the industry recovered and saw many decades of growth. Through the middle stretch of the 20th century citrus defined Winter Garden's economy and culture.

In the 1980s, back-to-back freezes reduced the profitability of citrus farming in the county. Citrus production in Winter Garden and Orange County never recovered. Since then, the center of citrus production in Florida has shifted south from Orange County. The increasing development of the Orlando–Kissimmee–Sanford Metropolitan Area made it more profitable to sell grove lands to developers rather than attempt to restart them. Today, little citrus activity occurs in the city limits of Winter Garden. Yet, the town is proud of its citrus history; oranges and grapefruits continue to be symbols of the town.