Candidate Profile: Jessica Lee

First-time candidate Jessica Lee wants to give residents back their voice — an asset, she claimed, they’re losing.

“I want people, no matter who you are in this town, to feel like someone’s listening to you and truly considering what’s important to you,” the 34-year-old told VoxPopuli.

In an interview, Lee declared that the town council lacks transparency. She said that she wants to be a “voice for people who live here in town who feel right now that they don't have a voice and that there’s really nobody representing them.” She added that older residents remember a time when the town council was easily accessible, but “you now have to go through a set of glass doors” and schedule a meeting to talk to council members. 

Windermere’s continued growth and change also concern Lee, who works in sales and marketing at her parents’ company, High Gear Specialties, which produces mobile phone mounting accessories for vehicles. Pointing to the town’s Old Florida atmosphere, dirt roads and safe neighborhoods, she said most residents want the town to “stay what it is.”

To that end, Lee, an Orlando native who has lived in Windermere since 2008, is running for one of three seats on Windermere’s five-member town council. She squares off against incumbents Mandy David, Tony Davit and Tom Stroup and fellow challenger Frank Krens. The election is nonpartisan. Council members serve two-year terms and are unpaid.

The final day to register to vote in the March 11 municipal election is Feb 10. Early voting takes place daily, March 3-7, 8 a.m. to 5. p.m. at the Supervisor of Elections Office, 119 Kaley Street, in Orlando. The deadline to request a vote-by-mail ballot is Feb. 27 by 5 p.m. Vote-by-mail ballots must be turned in at the Supervisor of Elections Office by 7 p.m. on March 11. Voting on Election Day will take place 7 a.m.-8 p.m., at Windermere Town Hall, 520 Main Street. 

Boathouses in her backyard

The five historic boathouses in the lagoon at Palmer Park are essentially in Lee’s family home’s backyard. The legal wrangling dates to the mid-1980s, and the current legal battle over who owns the boathouses — seven residents or the town — factors largely in her campaign. In 2022, the town council terminated the boathouse owners’ month-to-month right-of-access leases and gave them 60 days to vacate the structures. The residents enlisted their own attorneys and fought back. Mediation and settlement offers have gotten nowhere. The matter is headed for a non-jury trial in August. 

Lee questioned the town’s claim that the boathouses belong to Windermere and wondered why exactly the council is pursuing the boathouses.

“Nobody’s really been able to get to the bottom of that. Why do they want these so bad? Why is the town willing to pretty much bankrupt itself to take these boathouses?” she asked. 

Residents, said Lee, want to keep the boathouse area the “perfect little ecosystem that it is.” She’s concerned that the town would transform Palmer Park’s placid lagoon, a favorite among naturalists, into a public kayak launch.

Lee is also worried that the town’s boathouse legal fees may divert money and resources away from road and drainage projects and the Windermere Water Masterplan — matters, she said, “that they’ve promised residents for years.”

The town council has steadily increased its legal budget to fight for the boathouses. In fiscal year 2022-2023, the town council budgeted $85,000 for legal services but spent $138,227. For fiscal year 2023-2024, however, the town budgeted $100,000 and spent $314,830. For the current fiscal year, which began Oct. 1, the budget is $225,000. Since the matter couldn’t be resolved through mediation, a non-jury trial is scheduled for August.

“At some point, they’re not going to be able to pay for our law enforcement, you know, other super critical things in this town, if they continue on the track that they are with their spending right now,” Lee said.

She also noted the effect the litigation has on residents’ taxes. Windermere increased the millage rate 7.20 percent for fiscal year 2024-2025. 

“The people who live here, who own these boathouses, are pretty much paying for themselves to get sued,” Lee said. 

If elected, she said that she would ask the “tough questions,” and would advocate to bring in third-party experts on real estate and land use law and “get to the bottom of the issue, no matter how many meetings it would take.” She also proposed an audit of town spending to identify where costs could be cut. 

Windermere already files an independent audit, conducted by the independent Orlando accounting firm McDirmit Davis, as part of the comprehensive annual financial report that is required by all municipalities with more than $250,000 in revenues or assets. 

Annexation, renovation, traffic 

Another area where Lee believes residents have lost their voice is with the Feb. 4 referendum to annex the Chaine Du Lac neighborhood into Windermere, especially since only registered voters in Chaine du Lac were permitted to vote.  

“We have nothing against the neighborhood, the people, nothing,” she said. “Major thing is, let’s let the current residents of the town of Windermere have a voice in that, let them vote on it.”

She also questioned whether the annexation would provide additional tax revenue to assist the town with the boathouse litigation or whether it would burden town resources such as the police department. In the six public workshops about the annexation, like this one from Sept. 24, 2024, town officials, like Windermere Police Chief David Ogden, reiterated that, Chaine du Lac’s 51 homes would have a negligible impact on town services like police and would require no additional officers or vehicles to serve the neighborhood. 

Regarding traffic, Lee suggested that the town is “growing too quickly” and that is negatively impacting its roadways. She suggested greater collaboration with the police department to study how to alleviate the congestion. She added that she wants to see speeding addressed. 

The Town Hall renovation plans have gone through multiple iterations. Lee said that she supports the project, but advocated including more input from residents and even tapping contractors and engineers from within the community to work on the renovations, although she did not discount using professionals from outside of Windermere.