City mulls options to keep its downtown charm

The historic fabric of Winter Garden remains largely intact; however, District 1 Commissioner Lisa Bennett believes the city is coming to a turning point.

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Initially settled in the 1850s, Winter Garden began to grow significantly after the arrival of the railroad in the 1880s. 

By the turn of the century, a small commercial district had emerged along Plant Street and residential neighborhoods began to appear.

The historic development of the area spans from about 1890, the date of the oldest remaining buildings, through 1945. With few exceptions, the historic buildings in Winter Garden date between 1915 and 1940.

In 2009, the City Commission created an Architectural Review and Historic Preservation Board to advise and make recommendations on new construction, demolitions, renovations and upgrades of buildings within the district.  

On Jan. 11, 2010, the City Commission adopted Ordinance 10-05, which established a Historic Downtown Architectural Overlay for the designated area in the city’s historic downtown district. The area is about 116 acres and includes 270 residential and commercial properties. 

“The city’s historic district is the heart of the community — it contains some of the city’s oldest, most treasured structures,” Planning Director Kelly Carson said. “The historic buildings tell the story of Winter Garden, helping us understand the social, cultural, economic and environmental transformations that have shaped the area.”

Recently, Carson said, the city also worked with a consultant to prepare an updated architectural survey of structures within the historic district and beyond. The city will be using those findings and recommendations to update the historic district regulations, potentially expanding the district and considering additional structures for contributing status.


The historic fabric of Winter Garden remains largely intact; however, District 1 Commissioner Lisa Bennett believes the city is coming to a turning point.

“The city is coming to a point where our comprehensive plan is reaching our maximum growth,” she said. “So we’re looking overall at more of a redevelopment phase, not so much development.”

City Manager Jon Williams agreed that as a city, the area is reaching build-out.  

“Moving forward we will be dealing more and more with redevelopment and infill development,” he said. “Infill development needs to be respectful and compatible with the existing environment. We need to just make sure our codes accomplish that.”

Although Bennett believes the city and staff have done a great job with allowing good development, the area is entering into a critical-mass phase in which the city has to be careful to protect the area — as well as to allow change. 

“The only thing for sure in life is change, and as a city, if you don’t, you’re stagnant,” she said. “What we’ve allowed to be developed I think has been good, specifically here in my district. Everybody wants to come here. That’s great, but as a commissioner I’m elected to protect the people (who) currently live here.”


At the City Commission meeting Thursday, Dec. 8, 2022, Bennett spoke of her district, in and around the downtown area, older homes being demolished and rebuilt, and how this is changing the character of the area. 

To preserve the character and protect the charm of the residential area surrounding downtown, she asked Williams to revisit a draft ordinance establishing a downtown residential overlay district. Another option she suggested would be to research the existing code for modification, which would place a size restriction on the residential buildings within the downtown district. 

Bennett suggested when demolishing a single-story home, a single-story home should be rebuilt in its place. She also suggested incentives for saving, remodeling or upgrading older homes — and possibly allowing additions within guidelines of the code. 

The city said maintaining balance is the key.

“The city is tasked with finding a balance between respecting individual property rights while maintaining the small-town charm that defines us,” Carson said. “It is a delicate balancing act that involves close coordination with a number of stakeholders including community members, land owners, developers, elected officials and other interested parties.”

From 2012 to 2022, the city has added one million square feet in the downtown area. The percentage value change for the downtown Community Redevelopment Agency in the same years is 187%. Projects that have been approved downtown throughout the past years include new apartment buildings such as on Tremaine and Boyd, mixed use with retail; Park and Plant, townhomes; Smith and Main, coming soon; and a new apartment building on East Plant Street.

Building addition projects that have or are expanding their commercial footprint include Plant Street Market, 2016; The Exchange, 2022; 161 S. Boyd St., 2017; 360 W. Plant St., 2018; expansion of the Whole Enchilada building adding a rooftop area, 2018; and Tremaine/Boyd, 2019.


As a Winter Garden native, Bennett has watched the downtown area transform first hand. 

“I know a lot of people (who) have lived in this area forever,” she said. “I know how proud the citizens are in my district, and I know that they have Winter Garden’s best interest at heart. They just want to preserve this way of life for their children and grandchildren.”

The main concern citizens have expressed is they want new structures to blend with the area without being overbearing and with no encroaching variances. 

The idea of preservation is not uncommon among cities. Many have adopted similar ordinances, which provide criteria for infill development and what a property owner can build on a property.

As a real-estate broker, Bennett said she has watched several of the older homes in the area be bulldozed and the values of the properties shoot through the roof.

“District 1 is a little unique in that it’s more individual investors that come here,” she said. “They’re like, ‘Well I love downtown. I want to move my family here and take part in that,’ because the city makes it a very desirable place to come and live.”

Looking forward, Bennett said she would love for residents to attend City Commission meetings.



Annabelle Sikes

News Editor Annabelle Sikes was born in Boca Raton and moved to Orlando in 2018 to attend the University of Central Florida. She graduated from UCF in May 2021 with a bachelor’s degree in journalism and a minor in sociology. Her past journalism experiences include serving as a web producer at the Orlando Sentinel, a reporter at The Community Paper, managing editor for NSM Today, digital manager at Centric Magazine and as an intern for the Orlando Weekly.

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