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Winter Garden at a crossroads: Growth plan proposed after small business shakeup

From Plant Street to Main Street: Businesses rebuild amid Winter Garden changes

WINTER GARDEN, Fla. – City leaders in Winter Garden are considering a new strategy to support small businesses after months of rapid change in the downtown district left uncertainty about what comes next.

A vote is expected Thursday on whether to bring in a retail consulting firm to help guide future growth and preserve the character of the city’s historic downtown. The move comes as business owners along Plant Street say rising real estate pressure and new property ownership lead to their leases not being renewed, having to deal with multiple closures and relocations.

Among the businesses impacted is Polka Dotz, a boutique that recently relocated after losing its lease. Owner Heidi Hardman said the transition has been sudden but manageable, with a new storefront secured just steps away on Main Street.

“We do have a new space and it is right around the corner,” Hardman said. “Our goal is to make Main Street the main street the go to.”

Other stores like Driftwood Market are also being forced to move out of their buildings along Plant Street. But like Hardman, They have announced they are planning to relocate along main street.

Following a packed public meeting weeks ago, Hardman said city officials reached out directly every day to discuss potential solutions and future plans for the area. Including what potential they could have to grow main street.

In a statement, city leaders said the proposed agreement with Retail Strategies Inc. reflects a continued commitment to small businesses.

“The City of Winter Garden has a longstanding commitment to supporting small businesses, which are central to preserving our community’s small-town charm. In continued alignment with this focus, the City is bringing a proposal to the CRA Board to partner with the consulting firm Retail Strategies, Inc., a company with a proven track record of helping small businesses thrive in similar communities through marketplace studies and target policy recommendations.”

The agreement would be for three years and the company would receive $50,000 annually by the city.

Still, Hardman said she has mixed feelings about the timing but is grateful something will be done and says she would be happy to receive help from the company.

“Is it a little too late? I don’t know,” she said. “Let’s move forward. We can’t control who buys what, but as residents we can choose where we spend our money.”

For now, foot traffic remains concentrated along Plant Street, and business owners say it may take time for customers to adjust to new locations.

“I think it will have an impact,” Hardman said. “A lot of the traffic for the next year or so will be on Plant, but when people realize their favorites aren’t there, they will go toward Main.”

Despite the uncertainty, Hardman said she remains hopeful and committed to rebuilding.

“We are going to make the best we can and be involved in this community,” she said. “I’m hoping this increases the support of small businesses.”

Polka Dotz is expected to open its new Main Street location in July, with a grand opening planned. Driftwood Market is planning it’s grand opening at 49 S. Main Street on May 30.


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