Winter Garden prepares to bring remaining East Winter Garden properties into city

East Winter Garden still contains pockets of land, or enclaves, governed by Orange County. But that won’t be the case for much longer as officials in the city of Winter Garden prepare to annex the remaining 60-plus, county-governed residential properties in the historic Black neighborhood.

Annexation will be on the city commission agenda Jan. 27, City Manager Jon Williams wrote in an email. The commission will vote on what’s known as an inter-local agreement — the contract between Winter Garden and Orange County that allows for the property annexation. Winter Garden Mayor John Rees is then expected to sign it. After that, the Orange County Commission will vote, agreeing to the annexation, followed by Mayor Jerry Demings’ signature.

Annexation is key to the city’s redevelopment plan for the East Winter Garden neighborhood that also includes extending the Community Redevelopment Area (CRA) through 2030. The CRA will allow city tax revenues above a baseline set in 1992 to be funneled into the community for improvements.

“Ninety percent of those funds will go into East Winter Garden. Fifteen million dollars gives us a nice pot of money to work with,” then-City Manager Mike Bollhoefer said in a July interview with VoxPopuli.

Once they come under the governance of of the city, rather than the county, East Winter Garden residents in those 60-plus homes will be able to serve on community boards, have a voice in city affairs and get discounts on city cemetery plots and rentals of Tanner Hall and the Jesse Brock Community Center, said Jamie Holley, president of the community advocacy group One Winter Garden and a member of the Community Redevelopment Agency Advisory Board.

Two years in development, the annexation process was nearly derailed over which government entity would fix the neighborhood’s long-standing drainage issues and whether one particular area, bordering Ocoee and close to State Road 429, fit the legal definition of an “enclave” and could be annexed.

“We worked out a deal with Orange County,” Bollhoefer said. “They have a master plan to fix that drainage problem. Part of our agreement is that they’re going to finish their design and fix the drainage issue, so we don’t have to.”

The greater obstacle was the enclave issue. An enclave is land owned by one government surrounded on all sides by land owned by another government — such as the houses on a block in East Winter Garden. The houses might be on a couple of parcels of county land while the rest of the block is owned by the city.

“It’s one community divided between two governments. You have the sheriff patrolling one side, and the city patrolling the other side,” said Bollhoefer. “Enclaves are a nightmare to manage.”

Indeed, city code enforcement rules don’t apply. Emergency 911 calls get routed through the county so response time can be longer.

“We made a determination over 20 years ago that we were going to annex every enclave when we can. It’s not as easy as one thinks. This took two years of work to get this done. There were some legal complications.”

In the case of the enclave that almost thwarted this annexation, it wasn’t bounded on all sides by Winter Garden. One side bordered Ocoee, “and that’s what threw the whole thing into disarray,” said Bollhoefer. 

Still, he continued to sift through the Florida statutes looking for a way to make it happen. “Then our attorney said Aha! I have an idea,” he recalled.

City attorney Kurt Ardaman’s solution turned on a secondary definition of enclave in the statute, one that involved a natural or constructed barrier, like a canal, fence or railroad, on the side of the enclave not bounded by Winter Garden that prevented traffic access to the enclave except through the city. “If you couldn’t get to the enclave any other way except through the city, I thought that might apply,” Ardaman said in a phone interview Wednesday.

Ardaman examined the area via Google Earth and walked the property himself. Then he presented his idea to the county attorney.

“No one had ever thought of it,” said Bollhoefer, pointing out vestiges of a canal on an old city map. “The county attorney said, It’ll stand up. We’re good.”

“Most people would have looked at this situation and said, You can’t do it,” said Ardaman. “This is one of the things that makes law fun. I love when someone says something can’t be done, and then you make it happen.”

City Commission meetings are held the second and fourth Thursdays of the month at 6:30 p.m., at City Hall, 300 Plant St., Winter Garden. Residents are encouraged to attend. Miss a meeting? Catch up with our exclusive video archive!