Could New Garage Near City Hall Solve Park Avenue Parking Woes?
City officials recently agreed to explore a public-private partnership to build a garage to alleviate perceived shortage of spaces in business and shopping hub
April 20, 2026
By Beth Kassab
Winter Park will put out a call for ideas to build a new multi-story parking garage near City Hall, the latest step in the city’s chase to solve what many consider to be a parking crunch near Park Avenue where street parking has traditionally been free.
The decision resulted from a discussion earlier this month at a meeting of the Community Redevelopment Agency board made up of all five elected city commissioners plus Hal George, the luxury custom homebuilder who serves as the agency’s appointed community representative.
At least one developer has already approached board members with a public-private partnership concept for a garage that could add 360 spaces behind City Hall, said City Manager Randy Knight.
Knight did not discuss details of the plan, but suggested the city could put out a call for competitive proposals as “a solution to help bridge the funding gap” that has prevented earlier pushes for garages from going forward.
George, founder of Parkland Homes as well as the local Habitat for Humanity, said he’s been around long enough to have seen his share of parking studies and doesn’t recommend another one.
As an employer near the avenue, he conceded that employee parking is part of the problem. But he’s still against adding paid meters to spaces, a move the city has long considered a nuclear option because of strong opposition.
“I don’t know why we wouldn’t at least explore the public-private partnership,” he said.
Knight said there was a proposal to add paid parking meters on Park Avenue around the time he arrived in the city in the 1990s and staff were “run out of town on a rail.”
He equated discussions about paid parking on the avenue to being as heated as debates about brick streets and dog parks. In Winter Park, that means white hot.
Mayor Sheila DeCiccio noted that the city already has two pieces of land that could be used for a garage — the lot behind City Hall and one near the train station.
She expressed frustration that Orange County officials have been unwilling to allow Tourist Development Tax dollars, the 6% surcharge on local hotel rooms that brought in another record $38 million in February alone, to help pay for the garage.
“I’ve said, ‘We’re the No. 1 tourist destination after the attractions … we’re the city of arts and culture’ and they’ve said no,” DeCiccio said, adding that she doesn’t believe any federal or state grants are available for the project.
She also said she is in talks with SunRail to provide more weekend service during special events like the art festivals, but the commuter rail system is still a long way off from regular weekend service to help alleviate some of the busiest days of the year.
DeCiccio said she tried to find a way to use empty spaces in the Bank of America garage and one near Panera Bread, but the owners have pledged those spaces to tenants so those discussions proved unproductive.
She said the clear choices are to enter a public-private partnership, issues bonds for the construction or somehow charge for parking with potential exemptions for residents.
But there was clear support for exploring that option over issuing bonds or charging for parking.
The group did not discuss specifics of what that deal may look like.
Commissioner Kris Cruzada said he’s noticed a worsening shortage of parking even on the north end of Park Avenue as he picks his son up from school.
“People are parking on Cole and Whipple [avenues] … you used to not see that and now I’m seeing more of it,” he said.
He said SunRail or even self-driving cars could eventually alleviate some pressure, but for now he wants to make sure visitors to Winter Park have a positive experience.
“We’re in such a tight margin of error that can make or break the impression of what people feel when they come to Winter Park,” Cruzada said.
Commissioner Warren Lindsey agreed that the lot behind City Hall is the most logical space for a garage. And he suggested the commission consider murals, artwork and ways other cities have helped parking garages blend with the local aesthetic.
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Wonderful news! Pay for something other than a park!
Would love to see more EV chargers as options in this garage, as we don’t have many.
Gabriel why should tax dollars pay for your transportation convenience? I’d like a gas pump next to City Hall for my vehicle’s convenience too, but I doubt the City will provide it. Guess I’ll have to just drive on over to Wawa by WP Village. But hey, couldn’t you charge up there too?
It’s very hard to play catch up after years of pretending there was no shortage of convenient parking. Consistently reducing the parking required to build anew was fairly intentional by past commissions. Garages are the inevitable answer to parking shortages caused by these reductions. Staff chose to label it “parking modernization” as the changes were proposed. Then too, consistently permitting Rollins to expand across Fairbanks Av without requiring Rollins to provide parking for any of the new uses was not helpful to the parking cause. This applies to the major Alfond expansion as well as the (massive) new Rollins Museum and biz school. A garage seems to be the only answer. This will only be helpful IF the entire garage is not reserved for private business as occurred with the Canton/Panera garage. Big garage but majority “Reserved” parking- except top levels. I would like to see preferable treatment afforded to WP residents in any proposed parking “solution”. (The big, overparked bank and office buildings were always the exception and should not have been allowed to become the rule.) Parking technology and apps are always discussed but not implemented.
The “Panera” garage was built for the 3 story retail/office that replaced the Jacobson’s building and their surface parking lot. During the city approval process for the new building, the city asked the owner if they could tag along and build 2 more floors on the garage for free public use. The retail/office building has the code required parking requirement for the retail and office tenants. The top 2 floors of free public parking are excess, built at taxpayer expense. Seems like a smart idea to me.
A new parking garage is definitely needed. However, I do not see any scenario where there would be 100% free parking. There needs to be a revenue stream whether it be a Public-Private partnership or one built via a bond issue.
Give the top level for parking for those employed on the Avenue and thereabouts. Charge a modest amount for the use on a monthly basis or as used daily. Maybe their employer provides them a parking card.
Charge for parking for everyone else, but maybe provide for the first hour free.
There would still be plenty of free parking throughout the downtown area.
Just my two cents
Garage near city hall would be OK. One by RR station would be an abomination next to the park.
We have been debating parking for over 50 years! Enough talk! When will we finally do something about it?
I have been a Winter Park resident for 30 years and have walked Park Avenue many times. Because there are no lines drawn for the spaces on Park Avenue, there are a lot of places where there could be more people parking, but can’t. I have brought this up to the city before, but they responded that they didn’t like the look of lines. I replied that you only needed lines that were perpendicular to the curb and never heard anything else. I counted almost 20-30 more possible spaces. Before the city votes to put up another parking garage that the city will have to purchase bonds for and we will as residents will have to pay off, try being more creative with the spots you already have.
New Parking is very much needed if you’re not downtown very early it’s almost impossible to find a place to park. Less closing of Park Avenue for things like a luxury car show this past Sunday would be greatly appreciated. I understand they left their former venue because they were being charged. Did they pay the City of Winter Park anything. They were selling cars. I was going to shop on Sunday for things I needed and sales were happening. Unfortunately I wound up shopping online much to the loss of my favorite stores on Park Ave. This was not the first time and unfortunately I’m pretty sure it will not be my last. A new garage with a small fee would not be a bad thing. Also as mentioned Rollins sharing some of their parking with outsiders would be good. People that want to go to an activity there have to park on the downtown side of Fairbanks also.
A garage behind City Hall makes good geographic and common sense to accommodate employees and city visitors. If paying for it is an issue, I’d think the businesses that rake in revenue from city visitors up and down Park Avenue should be tagged as one source for garage building expense.
Does anyone else find this location particularly convenient for Rollins College besides me?
No.Where in “ downtown “ Winter Park could a new parking garage go that wouldn’t be convenient to Rollins? Just stop…with this Rollins conspiracy nonsense.