Living in the Sunshine State – and Loving It

City of Winter Garden, FL
Written by David Caldwell

A silver lining to the pandemic is the new-found viability of remote work. As we discover that work may be performed from anywhere, where we live becomes more important than ever. In Central Florida, a community that’s both new and historic is offering the opportunity for better, simpler living.

Just 14 miles (23 kilometers) west of the bustling entertainment Mecca that is Orlando, a far different community is taking shape.

The rapidly-growing town of Winter Garden, with a population of slightly under 50,000, is poised to attract a wealth of new business thanks to its ready-made infrastructure and a strong emphasis on quality of life. While Orlando might be nice to visit, Winter Garden is where to live.

Settlement in the area dates back to the 1850s, when settlers and farmers were attracted by the rich farmland watered by the swampland of nearby Lake Apopka. The community grew steadily around the two railroad lines that were laid through it; today, two state highways provide connections and a similar spur to growth across Orange County.

Old-town hometown
After being formally incorporated in 1908, agriculture and industry continued to expand. Growth sadly slowed in the 1960s due to heavy area pollution, and residents moved to other communities. Yet this has proven to be a blessing for Winter Garden; while nearby communities continue to modernize their architecture, the town’s downtown area retains its historic, old-town feel and opulence.

Indeed, Winter Garden’s historic downtown – named to the National Register of Historic Places in 1996 – remains one of the town’s main attractions. Since that time, the area’s buildings have been maintained in a shining example of historic preservation, showcasing buildings between 80 and 110 years old. The area offers a rare glimpse of a bygone era, keeping the town’s heritage intact while looking to the future.

City Manager Michael Bollhoefer remarks how Winter Garden has deliberately set out to become an alternative to entertainment-focused Florida towns like Orlando, Tampa and Palm Beach.

“We wanted to make sure we would differentiate ourselves,” he says, and the results are clear. “It gives people something different from what everyone else in Central Florida has.” As part of this, Winter Garden’s downtown boasts bookstores and small retailers in addition to restaurants, creating a unique feel. “It’s more like the hometown or small town when you were growing up,” he says.

In addition to the downtown, Winter Garden is investing heavily in natural preservation.

At 200-acre Tucker Ranch, located in central Winter Garden near scenic Johns Lake, new amenities for family entertainment are being developed. Just as in its downtown area, Winter Garden’s newest project intends to preserve old-style Florida. Sub-sections of the Ranch will include a greenhouse for organic foods, a health & wellness park, an outdoor kitchen for al fresco cooking classes, outdoor exercise areas, walking paths, and launching areas for canoes and kayaks.

An additional park nearby provides walking trails for active senior residents, providing fun for all ages. Finally, Winter Garden’s Farmers Market – named among the ‘Best of the Best’ by Orlando Family magazine in 2020 – will soon enjoy a major expansion. “Those are all great quality-of-life things, plus the downtown,” Bollhoefer says.

This carefully cultivated quality of life provides fertile ground for business development.

Over 2,000 businesses call Winter Garden home, either through their headquarters or satellite offices, resulting in 25,000 local jobs and a highly diverse economy. “We cast a broad net,” Bollhoefer says.

Plan your escape
While still honoring Winter Garden’s agricultural roots with a wide variety of food production and agribusiness, the town also boasts advanced electronics and heavy construction. Schmid Construction, Central Florida’s largest construction contractor, is one of those who have relocated their headquarters to Winter Garden to escape Orlando’s crowded environment.

Bollhoefer says Schmid, among many other recent arrivals, specifically relocated to Winter Garden for its easy living and relaxed quality of life. It was not the executives but the employees who largely decided to make the move, he notes, further confirming Winter Garden’s attractiveness to employees, and especially, to families.

As part of the town’s focus on small business, Winter Garden’s business community thrived throughout the pandemic due to what Bollhoefer terms a measured response.

“We got it just right,” he says, pointing out that Winter Garden did not react as some other communities did. A rapidly-implemented Curbside and Outdoor Dining Program for the downtown area allowed restaurants to continue operating while following health guidelines, with the added benefit of having diners enjoy meals in Winter Garden’s outdoor splendor.

“In effect,” Bollhoefer says, “our restaurants started making more money after the pandemic arrived than they did before.” The program continues today despite a relaxation of health guidelines in March, reflecting its continued popularity.

“Love Local”
In other business sectors, Winter Garden’s city commission implemented its ‘Love Local’ campaign last fall, intended to stimulate small business recovery. Year-long community events helped show residents the value of small-town business and bring the community together.

These and other measures help ensure that Winter Garden’s characterful ‘Mom and Pop’ businesses continue to thrive and remain part of the town’s unique aesthetic.

For larger companies, Winter Garden is investing heavily in infrastructure development to provide ready-made work environments.

A new office building downtown, the product of over $1.5 million in investments, will provide 42,000 square feet of restaurant, retail and office space. One business has already set up shop, with others on the way. This new facility, Bollhoefer says, will provide stable jobs in the heart of Winter Garden. “Those that are working in offices want to be in a place where they really enjoy being, where they can walk out and get lunch. And it makes for more productive workers,” he remarks.

This building, and others under renovation, will help Winter Garden adapt to future “hybrid” jobs, in which employees balance remote and in-office work on different days. This office building is an example of the “clean office” that Winter Garden hopes to operate in the future.

“I think you’ll see fewer office buildings being built, and more people working from home,” he says, “so we have to adjust to that.”

The right priorities
A consequence of this move to a hybrid form of working is the need for a more robust telecommunications system – an infrastructure necessity along with electric, water and sewer lines in 2021.

“We’re looking at all our options for that,” Bollhoefer says, remarking that it has to be a priority as Winter Garden shows every sign of maintaining its rate of growth. “We’re fortunate that we have a pretty good system here. We didn’t have any issues during the pandemic.”

Improving and expanding internet connectivity is just one of Winter Garden’s priorities moving forward. Storm water mitigation, a consequence of climate change, remains a primary concern. Bollhoefer says that Winter Garden and surrounding communities now receive “once in 30 years” rainfalls more or less every year.

While not approaching critical levels, storm water will be a main focus as the town grows. “We’re having to redo and rethink a lot of our stormwater infrastructure, to make sure it works,” Bollhoefer says. “We’re very proactive, so we’ve been out ahead of the curve on that.”

Road construction is an even larger project. As Winter Garden and its surrounding communities grow, road networks will struggle to contain a rising population. The town is now working with its surrounding communities to explore new transit and transportation options.

“We’re looking at how we can work together to improve the transportation,” Bollhoefer says. He notes that Orange County may be exploring mass transit options in the coming year. “I think a year from now, they’re going to be bringing that back, and we’re going to all work together.”

Growing with care
Both of these projects will help Winter Garden continue to grow unimpeded. Thanks to the town’s pre-determined limits, Bollhoefer and his colleagues have intricate and detailed land strategies for Winter Garden’s surrounding land; some plans extend 20 years into the future.

There are plans for three new residential and commercial areas, as well as plans to redevelop some of the town’s older houses into newer, smaller dwellings suitable for couples and small families. “We pretty much have the entire city planned out,” Bollhoefer says, but allows for adaptation. “We also realize things change, so you have to be flexible and modify your plans as needed.”

As Winter Garden looks forward to a COVID-free future, the town is continuing to adapt – by staying the same. By choosing to differentiate itself from entertainment-focused Orlando, the town has rapidly transitioned from a suburb to one of Central Florida’s finest and fastest-growing communities.

For those people and businesses seeking an attractive alternative to today’s over-hectic environments, Winter Garden – where they’re living in the Sunshine State and loving it – is ready.



Up in Smoke

Read Our Current Issue


To Make a Northwest Passage

May 2024

From Here to There

April 2024

Peace of Mind

March 2024

More Past Editions

Cover Story

Featured Articles