Winter Garden, Florida Real Estate

About Winter Garden, Florida

It was 1857 when Becky Roper Stafford’s great-great-grandfather first glimpsed 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 Meriwether 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, a gristmill, a sugar mill, and a cotton gin. Later he built a tannery for making shoes and served as Orange at 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, marking the humble beginnings of an industry that would sustain and define Winter Garden, which had been incorporated in 1903, for the next six decades. Winter Garden remained an idyllic small town throughout World War II and into the 1950s and 1960s. Far removed from Orlando, which was about to be reshaped by the advent of Disney World, the city remained self-sufficient and unpretentious. “Winter Garden was the quintessential vibrant small town,” says Stafford. “We had the distinction of being the only town with two train depots because it was such a busy shipping community with fresh fruit going all over the world.”

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 passed 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.

Today locals and outlanders gather at Choctaw Willie’s in the reopened Edgewater Hotel for barbecue, collard greens, and sweet tea. Just down the street, Winter Garden Pizza Factory is all about pasta, fresh pies, and family fun.

Lakeview Park on the 30,862-acre Lake Apopka is also the north side of town. The south side of town is newer. Modern shops, restaurants, movies theaters, and housing subdivisions can all be found in the south Winter Garden area. Most of your shopping and dining choices can be found at The Winter Garden Village.