
Winter Park city leaders this week advanced a plan to create a paid parking pilot program at Lake Baldwin Park and Dinky Dock, effective next year, as the city explores ways to bring in extra city revenue.
The goal of the pilot program, according to city documents, is to “to modernize management, improve operational efficiency, and offset expenditure cost to support municipal services.”
The city claims that requiring visitors — many of them not residents of Winter Park — to pay to park their cars would “enhance” the parking experience for all.
Residents of Winter Park would be able to continue to park at the dog park and Dinky Dock for free, under the proposal, if they registered their vehicles with the city and received a permit. The six-month pilot, first discussed during summer budget talks, still needs to be drafted as a city ordinance for final approval by the city commission.
If approved, it’s expected to roll out in spring 2027.
“I’m in favor of the pilot program,” said city commissioner Craig Russell. “It might ruffle some feathers,” he added. “I think tracking the behaviors at those parks will give us good indicators on how to use this most effectively, you know, for our residents.”
Parking rates at the two parks would likely be in the range of $2 to $3 an hour, according to city staff, or a flat rate of $20 per day. Winter Park residents would be able to register two vehicles per household for permits in order to park for free. Those permits — requiring proof of residency, like a utility bill — would need to be renewed by residents annually.
Although the pilot program concept was approved by the five-member Winter Park Commission unanimously, not everyone in the community is on board.
“Baldwin Park is a regional gathering place,” noted Eric Paul, president of the nonprofit Friends of Winter Park Dog Park, during the public comment portion of the discussion.
“People from Baldwin Park, Audubon Park, Orlando and beyond — they stand alongside Winter Park residents as one community. Charging these neighbors to park risks dividing the community we should be proud to bring together.”
“Charging these neighbors to park risks dividing the community we should be proud to bring together”
Eric Paul, president of Friends of Lake Baldwin Dog Park
Paul said his group of volunteers, made up of both Winter Park and non-Winter Park residents, was created to help fill gaps in city staff’s maintenance and upkeep at Lake Baldwin Park. “The people doing the work should be included before paid parking is proposed,” Paul argued.
According to city staff, both locations — Dinky Dock near Rollins College and Lake Baldwin Park — were chosen for this pilot project because they believe it’s unlikely that creating paid parking will cause an overflow of traffic and push desperate parkers into neighborhoods instead.
“That’s not impossible for it not to happen,” admitted Kyle Dudgeon, the city’s economic development assistant division director. “But we certainly think that there is some value in looking at an area like this where we feel like something could be plausible here more than other areas.”
City staff noted that other neighboring cities like Orlando, Sanford and Mount Dora have recently held similar discussions around paid parking. “Winter Park is not the only group having this conversation.”
Florida municipalities, currently in budget season with the current fiscal year ending Sept. 30, are also preparing for a potential loss in property tax revenue, if Amendment 3 is approved by more than 60 percent of voters this fall.
State economists estimate that if Amendment 3 is passed, expanding Florida’s homestead property tax exemption, local governments in Florida could lose out on roughly $5 billion collectively in the first year of implementation, with that number steadily rising thereafter.
“Revenues generated may be appropriated by the City Commission to support municipal operations, capital projects, public infrastructure, or other community priorities through the budget process,” according to city documents pertaining to the pilot parking program. “In addition to revenue considerations, the program is expected to improve parking turnover, encourage efficient use of public parking resources, reduce congestion in high-demand areas, and provide data-driven insights for program efficiency.”
City commissioner Elizabeth Ingram asked if the pilot parking program might be expanded to other parks or city areas in the future. According to city of Winter Park staff, the answer is, at this point, to be determined at a later date. “The scalability of it is, I don’t think, as important today,” said Dudgeon.
City staff and commissioners will have further opportunities to amend or adjust the details of the pilot program as staff draft an ordinance for city commissioners to review, then approve or reject at a later meeting date.

