Winter Garden: 10 Great Places to Live in Orlando in 2023

Downtown Winter Garden offers great shopping, dining, and room to hang.

Photos by Roberto Gonzalez

Winter Garden began as an agricultural town nestled on Lake Apopka. Once on life support as pollution ravaged the famed fishing lake and freezes killed the citrus industry, the community rallied to revitalize its environment, economy and history to become a role model to other towns.

Now the booming town has become a destination and an incubator for business. “It was basically a local grassroots group of people who wanted to save their downtown,” according to Jim Crescitelli, director of operations and programming for the Winter Garden Heritage Foundation.

The foundation worked hand in hand with city and county officials to save the historic Edgewater Hotel, now a bed and breakfast with restaurants, along with two train depots. Museums opened. The Garden Theatre was restored. In 1996, the area’s commercial and residential districts earned a spot on the National Register of Historic Places. The West Orange Trail came through. 

“People coming through on the trail and people living here said, ‘You know, there are a lot of empty storefronts. Let’s do something about this.’ People started opening up shops,” Crescitelli says. Downtown was reborn, and commercial and residential developers swooped in, with an eye to reflect the city’s historic architecture.

Neighbors frequent Plant Street Market.

The town’s resurgence has been “incredible,” he says, with the tens of thousands of visitors each year serving as a testimony. “You can’t walk down the sidewalks some Fridays and Saturdays because it’s so busy,” he says. 

“People come here from other towns to see how we did it,” he adds. “We’re on the map. We have the shops. We have the restaurants. We have a welcoming feeling.”

But the family-friendly city, with its median age of 40 and median home price of $550,000, continues to retain its small-town charm. Its Saturday morning farmer’s market is ranked among the top in the state. Festivals frequent the city’s calendar.

Neighbors frequent Plant Street Market.

Centennial Plaza, with its clock tower and mosaic fountain, serves as the community’s hub and provides the setting for live music on Friday nights. Brick streets echo back to Winter Garden’s historic roots, while new construction mimics the city’s iconic architecture.  

Crescitelli is encouraged to see people so determined to learn and preserve the city’s unique history.

“We want people to know what was here before them and how they can help make it very special going forward.” —Jim Crescitelli, director of operations and programming for the Winter Garden Heritage Foundation

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