History of a charming little city with a juicy past

Settlers began arriving in the Winter Garden area by the 1850s, attracted by the fertile muck land that bordered Lake Apopka.  They engaged in citrus and vegetable farming, living in small settlements situated along the lake's south shore.  By the end of the nineteenth century, Winter Garden's business district had grown up alongside the two railroad lines that ran through the city.

The commercial buildings were rebuilt with brick after two fires destroyed the wooden buildings and packinghouses that stood along Plant and Main Streets.

Winter Garden was established in 1903 and officially incorporated as a City in 1908.  The first Mayor of Winter Garden was A.B. Newton. The population of Winter Garden had grown to over 1,000 people by 1920, and the city had quickly become the center of commerce and agriculture in West Orange County.  Lake Apopka's emergence as "the large-mouth bass capital" attracted tourists, and the Edgewater Hotel opened in 1927 to accommodate these visitors.  Early residents either owned or worked in the groves.  As the citrus industry grew in importance and acreage, the commercial district continued to expand.  

Winter Garden's rapid development slowed considerably in the late 1960s.  Lake Apopka had become severely polluted, and the construction of major highways in the area drew businesses away from downtown.

Despite the challenges, Winter Garden's architectural heritage remained intact.  The establishment of the West Orange Trail attracted thousands of visitors eager to patronize the new shops and restaurants that moved into the old buildings.  In 1996, downtown Winter Garden was listed on the National Register of Historic Places after concerned citizens and community leaders rallied to rescue the commercial district.

Today, Winter Garden's Historic District serves as a successful example of historic preservation.  Infill development, redevelopment, repurposed buildings, preservation, housing and businesses all converge to create a thriving downtown that draws people from around the world.

Thank you to the Winter Garden Heritage Foundation for contributing to this page.

This circa 1950 view looking west along Plant Street shows structures that still stand in the Historic District; the taller building at left now contains only one story.

History Photo 1 - Plant Street

The South Lake Apopka Citrus Growers Association packinghouse in Tildenville, a community located on the west side of Winter Garden. The building, now housing various small businesses, still stands on Tildenville School Road.

History Photo 4 - Citrus PackingPlant

Citrus workers with the Britt Fruit Company that was located for many years on East Plant Street.

Photo of two white and two black men in front of a tractor

An Atlantic Coast Line train arrives at the depot located at the intersection of Plant and Main Streets. This depot, constructed in 1906, replaced an older structure located nearby. In 1923, it was replaced with the brick structure that stands today – the home of the Winter Garden Heritage Museum.

History Photo 5 - Train Station

The Lakeview High School band marches along Plant Street in this 1955 photograph. Some of the structures seen in the background, such as the Garden Theatre, still stand today.

History Photo 2 - Parade

Future Winter Garden City Commissioner Bob Buchanan displays his catch in this 1957 photograph taken at the Gap fishing camp on Lake Apopka.

History Photo 6 - Bob fishing

Harry E. Bumby displays a fish caught in Lake Apoopka, at one time the “large-mouth bass capital of the world.” Bumby operated a hardware store on Plant Street.

Hitory Photo 5 - Fisherman