Winter Garden’s historic district was born in the boom times of the 1920s, and it remained a vibrant, active hub of the city until the mid to late fifties. This period of decline was spurred, in large part, by an explosive overdevelopment on highway fifty that lead people away from the downtown. In those later years of the twentieth century, the historic buildings of downtown faced a new threat of being destroyed in the shadow of this new construction. After years of being targeted by the City, the Edgewater Hotel was narrowly saved by a small group of people from being demolished in favor of a parking lot. Reflecting on this history in 2003, City Manager Hollis Holden had said "The city, quite frankly, did not make wise decisions in the direction they were trying to go with the hotel."
The rebirth of downtown Winter Garden came as a result of the preservation of the historic district. They stood out as something special and unique, and they were an enduring symbol of Winter Garden’s cherished history. The initial downtown redevelopment was done in conjunction with the restoration of these historic buildings, and that combination brought success and traffic back to downtown. The Historic District was founded to make sure that the special history and designation of this area of Plant Street running from Dillard Street to Main Street never be overlooked again.
Today we are facing the prospect of history repeating itself. This time the overdevelopment of new construction within the historic district is threatening to overrun the family-friendly charm of our small town and turn it into a mini-Orlando. The success of the restoration of downtown has brought in a new group of citizens who are unfamiliar with the history of our town. While we welcome them to our community and appreciate their enthusiasm for continued economic development, we need to inform them of the pitfalls of unbridled and unexamined growth that plagued our past. Even Mayor Rees has expressed some reservations about the proposed site of a new three story hotel in the historic district, stating "this is not the first site I would pick."
Winter Garden has room to grow. It’s new population is over 40,000. Even Plant Street is seeing new development on the other side of Dillard by the 429, outside of the historic district. As a community, we need to make sure that our voice is heard in the management of this future growth. Instead of turning our historic district into a condensed and crowed city center and building another three story building in our backyards, we need to explore the opportunities that exist in these newly developed areas of Winter Garden where a new history can emerge without confusing and ultimately erasing the past.