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Downtown - Plant Street

Lake Apopka

Heritage Museum

West Orange Trail

Winter Garden Village

It was 1857 when Becky Roper Stafford’s great-great-grandfather first glimpsed at Lake Apopka. W.C. Roper was riding through the backwoods of west Orange County on horseback, seeking a place to build a home for his family waiting back in Merriwether County, GA.

Roper bought 600 acres along the shore, between present-day Winter Garden and Oakland, and returned a year later with his wife and 10 children. The ambitious settler operated a sawmill, gristmill, sugar mill and cotton gin. Later he built a tannery for making shoes, and served as Orange County’s superintendent of schools from 1873 to 1877.

Fast-forward to the 1920s, when Roper’s son Frank planted the area’s first orange trees, making the humble beginnings of an industry that would sustain and define Winter Garden, which had been incorporated in 1903, for the next six decades.

Fast-forward again to the 1980s, when devastating freezes destroyed thousands of acres of citrus. Roper Growers Cooperative, Heller Brothers and Louis Dreyfus Citrus eventually recovered. But as growers regrouped or retreated, once-bustling downtown Winter Garden became a virtual ghost town.

Concurrently, developers began buying up decimated groves for new homes, creating new subdivisions seemingly overnight. But most of the residential growth, and the retail growth that followed, was outside the city, which made Winter Garden proper even more of an anachronism.

Then came a brilliant project called Rails to Trails, through which abandoned rail beds across the country were converted into hiking and biking trails.

The popular West Orange Trail passes directly through Winter Garden, thus converting the all-but-forgotten city into an oasis for thousands of ready-to-spend strollers. In fact, city officials estimate that the trail is responsible for generating about 50,000 downtown visitors per month.

And most are charmed by what they see. In 2001 the tired downtown district underwent a facelift. Brick streets were restored, old buildings were remodeled, and Centennial Fountain, saluting the city’s citrus-growing heritage, was constructed.

And locals proudly note that Winter Garden has two historical museums open seven days a week. There’s the Central Florida Railroad Museum and the Heritage Museum, both housed in restored depots. History buffs may also stroll around the city and view such landmarks as the 1860s-era Beulah Baptist Church.

And redevelopment is on a roll: Stafford is hard at work with the Winter Garden Heritage Foundation to renovate to historic Garden Theater on Plant Street, which will become a 300-sear performing arts center.

While the old downtown is re-emerging as a force to be reckoned with, several miles south a 1.15-million-square-foot open-air mall called Winter Garden Village at Fowler Groves is set to open soon. More than 40 new home communities are currently under way within Winter Garden’s city limits. And the city plans to annex a large tract of mostly undeveloped land from its western boundary south of Florida’s Turnpike to the Lake County line. The tract contains 1,300 developable acres that could eventually contain 3,600 homes.

To the south of downtown, along C.R. 535 and S.R. 545, communities totaling 25,000 homes are expected to be built where citrus groves once flourished.

The biggest of the new developments is Horizon West, a 38,000-acre master-planned community that has been in the planning stages for a decade. At buildout, its two villages – Bridgewater and Lakeside – will contain nearly 18,000 homes.