By Jim Carchidi
June 3, 2026
Parking options in downtown Winter Park may soon include a new garage. City staff have begun a two-phased vetting process for the design, construction, and funding of a 265-space structure at the current location of a surface lot behind city hall.
Ongoing issues
The need for more parking in Winter Park's shopping and dining district has been discussed for years with a lack of city funding as the sticking point. Photos by Jim Carchidi
According to a 2024 parking study, available spaces in downtown Winter Park total 2,709 on weekdays and 2,787 on weekends. The city has received complaints regarding availability during peak hours and accessibility issues for seniors parking at a distance from their intended destination.
Parking solutions have been a longtime debate at city commission meetings with proposals ranging from new parking garages to shuttle service to-and-from surface lots beyond the city center. Limited funds have kept ideas from moving forward, but a proposed public/private partnership utilizing city-owned property has gained the most traction.
Orlando commissioners recently approved the first reading of a proposed downtown parking rake hike to help fund garage upgrades and maintenance. However, the same funding idea would not go over in Winter Park as residents and city leaders have fought to maintain free access to city parking.
The discussion
The new garage would replace a 145-space lot behind city hall with a multi-level structure able to accommodate employees and visitors.
The garage partnership was presented as an agenda item at the May 13 commission meeting, where Mayor Sheila DeCiccio reiterated the need for a funding solution and the ability to retain free access to city-owned parking.
Commissioner Elizabeth Ingram hoped to find a less-permanent solution than new construction and believed the bland design of a garage could detract from Park Avenue's architectural appeal. Commissioner Craig Russell agreed the garage may not be the ideal fix, but said it was the best long-term solution.
"It doesn’t have to be ugly," he said of the design, "and it’s the only practical solution."
Commissioners Warren Lindsey and Kris Cruzada also supported the effort. Cruzada labeled the parking issues as an indicator of popularity, saying Winter Park has been a "victim of our own success," but adding the garage was a step in the right direction to solving the issue.
City manager Randy Knight agreed free parking access should be retained, but also noted a request for proposals that includes a funding partnership should not present multiple limitations.
"If we put too many restrictions in what we put out, then were stifling the creativity of how it can be paid for," he said.
A two-phased process
The first phase is a Request for Qualifications (RFQ) from development teams interested in a public-private partnership to build, finance, and operate the facility. Applicants will be vetted with the shortlisted teams moving onto a Request for Proposals (RFP) which detail design concepts, structured financing, and ideas for enhancing long-term value.
Additional project requirements listed in city documents include:
- adherence to city codes
- design compatibility with the surrounding area
- efficient vehicle access and circulation
Since the garage would replace the 145-space lot used by city hall employees and visitors, it must address those needs in addition to adding public spaces. At least 120 spaces beyond those provided by the lot will be required, for a minimum total of 265 spaces.
The deadline
The Phase 1 RFQ is currently in progress with responses due by 2 p.m. on July 15. The selection committee will meet on August 4 to vet applications and shortlisted teams will be notified of the Phase 2 RFP schedule.
Sponsor: The Orlando Real is sponsored by the Pozek Group — the #1 real estate team in Orlando and the Official Real Estate Team of the Orlando Magic.
About the Author
Jim Carchidi is an Orlando journalist and photographer with previous work at the Orlando Sentinel and Orlando Business Journal. He covers development, arts, culture, and local stories for The Orlando Real.
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