by Beth Kassab | Apr 30, 2026 | Arts and Culture, Historic Preservation, News
Orange Signs Herald May as Historic Preservation Month
Residents display their yard signs each year in support of maintaining what’s left of the pockets in Winter Park where 100-plus year homes are commonplace
May 1, 2026
By Beth Kassab
It’s that time of year when orange yard signs start sprouting up in yards all over Winter Park to mark May as Historic Preservation Month.
The signs are a longstanding tradition among preservationists who want to remind Winter Parkers of the benefits of preserving historic architecture and the eclectic charm that keeps the city at the top of the charts when it comes to home values.
Winter Park’s Historic Register lists more than 120 homes and continues to grow each year.
Historic districts in the city include College Quarter, Virginia Heights East, Interlachen Avenue and the downtown area centered on Park Avenue.
The city encourages those with designated homes or those who live in the districts to display their signs.
People who need a sign can pick one up at Casa Feliz on any Tuesday, Wednesday or Thursday from 10 a.m. to 2 p.m., said Betsy Owens, executive director of the Casa Feliz Historic Home Museum and a leading preservation advocate in Central Florida.
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by Beth Kassab | Apr 28, 2026 | City Commission, News, Orange Avenue Overlay, Zoning and Development
Plan for Former Orlando RV Dealership Draws Traffic Concerns
Residents close to the West Fairbanks Avenue property welcome new retail and restaurants but fear repercussions of bringing traffic to an area already considered congested
April 28, 2026
By Kathryn Brudzinski
Plans for a commercial redevelopment at the site of the former Orlando RV dealership along West Fairbanks Avenue are stalled, for now, after residents brought up concerns related to parking and traffic.
Winter Park’s Planning & Zoning Board will meet at noon today for a workshop to discuss the project and traffic concerns in the area of Fairbanks, Denning Drive and Kentucky Avenue. No vote is scheduled until the following board meeting on May 5.
During the board’s April 7 meeting members opted to push the vote until next month after hearing from nearby residents and representatives of the Holler family, which owns the property through DI Partners LLLP. Roger Holler III, great-grandson of Bill Holler – the former vice president of General Motors who founded the family’s automotive business – is listed as president of the company in state records.
DI Partners wants to build four one-story buildings totaling 29,760 square feet for shops and restaurants at the former RV dealership.
Though there appeared to be support for the concept, including a recommendation for approval from city staff, people who live nearby raised questions about parking and traffic.
“We just want to make sure it’s managed and mitigated so that way we maintain the accessibility and the safety for our neighborhood, for drivers, as well as pedestrians and cyclists,” said Sonia McLean, who lives with her husband on Kentucky Avenue. “…We’ve always embraced our commercial neighbors. We understand that concessions have to be made, we just want to make sure that we don’t lose the flexibility and charm of our neighborhood.”
Documents submitted to the city show the location of the proposed development to be known as Fairbanks Crossing.
The project’s approval is subject to certain conditions and other requests by the city, like the inclusion of on-street parking along Holt Avenue “to help calm traffic, provide additional convenient parking for patrons and create a safer and more comfortable pedestrian environment.”
Z Development Services Chief Executive Bob Ziegnefuss, who is managing the project, said the group plans to address each of the city’s conditions for approval, but said some issues like street parking would offer a “very limited benefit” as the project could likely only offer six to seven spaces.
“The concern that we have on the applicant side of this is that this could be an extensive cost for a small community benefit here to get that street parking, but we do want to look at it,” Ziegenfuss said. “We are committed to help and do what we can. I guess we want to hear tonight as part of the discussion, what’s the true desire here? There’s two different things that happen in a situation like this – is the desire to get parking or is the desire for traffic calming?”
While the project plans to provide a total of 199 parking spaces overall, exceeding the minimum code requirement of 175 spaces, concerns from residents centered around a desire for both accessibility to parking as well as measures to limit traffic.
Winter Park attorney Frank Hamner, longtime representative of the Holler family companies, said the goal is to construct the redevelopment in compliance with code while still satisfying the city’s needs and seeking the “least possible number of variances.”
“Even though we can under park this spot or park to code, we’re overparking,” Hamner said. “This is not us trying to force something through and asking for a bunch of variances. This is a long, thought out two-and-a-half to three-year process to get to where we are today.”
Renderings show what the proposed project could look like from Fairbanks Avenue.
Susie Stein, another Winter Park resident located on North Kentucky Avenue, said she is excited about the project, but her primary concerns also centered on parking, safety and how the increased traffic would affect her neighborhood.
“I know that they have overcompensated for the parking, but I don’t know how you control people from parking in this new shopping area who are going to be at the baseball games at Rollins, doing other things in the neighborhood,” Stein said. “So then the overflow parking is going to end up on our street, which is a very, very narrow street already, and when cars are parked on both sides, you are literally squeezing yourself through.”
The proposed redevelopment, which provides access from Holt Avenue and Capen Avenue, intentionally avoids offering direct vehicle access to Fairbanks Avenue and Denning Drive.
But Winter Park resident Brian Barnard, who also lives along North Kentucky Avenue, said the traffic on Denning Drive is at a point where it’s “already overloaded,” causing travel issues for him currently.
“My house is on the west side of Denning, and I can’t get out of our alley in order to get onto the street,” Barnard said. “I have to drive down Denning, probably two or three blocks, then turn around…I’m not saying that I don’t want this project — I just want us to be a little bit thoughtful.”
Board member Alex Stringfellow acknowledged residents’ concerns, saying there’s “an existing issue with traffic” in the area, but that when developments are reviewed by the Planning & Zoning board “traffic is not considered the applicant’s responsibility.”
“In this case, generally speaking, [the applicant’s] contributions to the city to provide turn lanes and so forth… is offsetting mathematically, what the traffic impact is,” he said. “[We] hear what you’re saying and definitely understand that there’s safety concerns out there. There’s a limited amount that we can do here on this particular item, because it represents a small percentage of the existing issue and contributes a small percentage of the ongoing issue.”
Board members ultimately agreed concerns regarding traffic and safety warranted further discussion before any approval could be made. As a result, the workshop was scheduled for today at noon.
“My gut feeling is that answering what makes sense on Holt Avenue from the applicant’s perspective and based on what’s existing out there may provide some answers to safe travel through that area, what parking is going to look like and how people will move in that area,” said Alex Stringfellow. “I don’t want to promise that all these problems are going to go away — it’s a very congested area.”
Correction: A quotation in the original version of this story was incorrectly attributed to Planning & Zoning board member Jason Johnson. The quotation has now been attributed correctly to Alex Stringfellow.
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by Beth Kassab | Apr 24, 2026 | City Commission, News, Zoning and Development
Preempted Again. New FL Law Prohibits Cities from Protection Against Damage from Internet and Cable Companies
Plus, the ordinance allowing construction of five Habitat for Humanity homes in partnership with Orange County Public Schools gains first necessary approval
April 24, 2026
By Kathryn Brudzinski
Winter Park Mayor Sheila DeCiccio expressed frustration this week that the state government is, once again, impeding the city’s ability to govern itself.
This time officials said they had no choice but to toss out a pair of ordinances designed to protect city roads, pipes and other assets from damage that sometimes occurs when communications companies such as AT&T or Spectrum run underground lines.
The new rules, which were scheduled to be voted on by the City Commission this week and would have required a bond from communication companies to pay for potential damage to the public right of way, were modeled off similar ordinances in Winter Garden.
City pipes, irrigation systems and roads often take on damage when the private companies move overhead lines underground or install new lines.
But Gov. Ron DeSantis signed Senate Bill 488 into law on Tuesday.
The bill includes a provision that limits cities like Winter Park from enacting financial protections against damages and other requirements on communication companies. As a result, both Ordinance 455 and Ordinance 456 are now unable to move forward, leaving the city with no choice but to find another way to protect itself.
DeCiccio said it can often be difficult for the city to seek financial restitution for broken pipes and other problems that occur from the private companies’ construction. According to the staff report, Florida statutes previously allowed municipalities to hold utilities “responsible for any damage resulting from the installation or maintenance of such facilities.”
“However, the governor signed Senate Bill 488 just yesterday and that won’t allow this,” DeCiccio said. “So, we’re going to go back to the drawing board and see what we can do.”
Ryan Mathews, a lobbyist who represents Winter Park and other cities in Tallahassee, provided commissioners with an update on the recent legislative session and said the limitations on city governments was ”tucked” into a large transportation bill and hadn’t received much discussion.
“It’s not a problem unique to Winter Park,” Mathews, of the GrayRobinson firm, said. “We hear quite often that contractors who cause damage are very slow to, if at all, ultimately pay for that damage. It’s certainly an issue that is ongoing.”
In Tallahassee, he added, larger bill packages often see provisions placed in the latter part of the legislative session at which point “there is very little that can be done about it.”
Still, DeCiccio questioned what the city could’ve done to combat the efforts of communication company lobbyists to include the provision if it’d been known about ahead of time.
“We could have made calls, we could have had you lobby on our behalf, because this is really bad for the cities,” she said. “This isn’t just Winter Park, this is all cities. This is terrible for us, it does nothing to help us.”
In recent years, the Florida Legislature and DeSantis have taken other steps — often referred to as preemptions — to limit the powers of local governments. Cities and counties can no longer protect the rights of residential renters, can’t enforce worker protections such as rules to prevent heat stroke for those who labor outdoors, must enforce a statewide ban on homeless people who camp in public spaces and can no longer regulate the use of Styrofoam products or artificial turf.
Habitat for Humanity and OCPS housing project nets first approval
Commissioners unanimously approved a zoning change this week to allow five Habitat for Humanity homes for public school employees to be built on the former Orange Technical College campus.
Habitat for Humanity of Winter Park-Maitland will be responsible for the development of five houses on the back end of the property along Webster Avenue still owned by the Orange County School Board.
The move is part of a greater effort by Orange County Public Schools to offer affordable homes to workers faced with the county’s housing crisis. ,“The plan would be to divide that area of the property into five single family lots,” said Planning and Zoning director Allison McGillis. “The only hiccup with the proposal is that within the PQP zoning district, detached single family zoning units are not permitted. So, the Commission gave direction to staff to move forward with this ordinance.”
In addition to the zoning change to allow the homes to be constructed, the Winter Park City Commission also offered up to $200,000 in funding for funding of water, sewer and other utility infrastructure for the property. The money had originally been allocated to help Habitat acquire new lots for homes, but the commission pivoted to the partnership with OCPS as a result of soaring land prices in Winter Park.
Jeff Briggs, the city’s former planning director who serves as treasurer for the local Habitat organization, said the project is moving along and explained its lease would cover much of the information commissioners may still have queries about.
“It’s the lease that answers your questions — it commits this property only to be used for homes owned by Orange County public school employees,” Briggs explained. “So if it’s time to sell, then they’re going to sell and recycle to other Orange County public school employees. They also have to remain income qualified, which means they’re not going to sell for half a million dollars, because the income qualified person couldn’t afford that.”
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by Beth Kassab | Apr 20, 2026 | City Commission, News, Zoning and Development
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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by Beth Kassab | Apr 8, 2026 | City Commission, News
Michelle del Valle Named New City Manager
Commissioners gave unanimous, enthusiastic support for del Valle (pictured above) to takeover when Randy Knight retires in January. Meanwhile, a split 3-2 vote approved increased hourly rates for the city attorney
April 8, 2026
By Beth Kassab
Winter Park City Commissioners voted unanimously on Wednesday to authorize Mayor Sheila DeCiccio to begin to negotiate a contract with Michelle del Valle to became city manager in January.
She will succeed Randy Knight, who has served in the position for 19 years.
Winter Park has a city manager form of government, which means the person in that job sets the tone and runs all aspects of the on a daily basis, helming more than 500 employees. The elected commissioners set policy, but the manager is largely responsible for overseeing the execution of policy.
Mayor Sheila DeCiccio said a national search to fill the job was unnecessary because she “wholeheartedly” supported del Valle, who has served as assistant city manager since 2008. DeCiccio cited del Valle’s education, experience and connections.
“She has the knowledge, the relationships, the contacts … and I can’t tell you how important contacts are to get things done,” DeCiccio said. “When we had the cold snap she was able to pick up the phone and call the people at Publix, at Advent[Health} to get them to turn on their generators so there wasn’t a drain on our [electrical] system.”
The four other commissioners also enthusiastically endorsed del Valle, who Knight named as his recommended successor as early as 2022.
Knight said in a letter to the commission that he will retire on Jan. 8.
Del Valle lives in neighboring Maitland and spent 16 years working that city before joining Winter Park, which has a population of about 30,000. She will be required to live in Winter Park as part of the city’s rules for the job.
Two commissioners expressed reservations about a second major hiring decision on Wednesday, questioning whether the contract for the city’s attorney should be put out to bid.
Kurt Ardaman and his partners at the Fishback Dominik law firm have represented the city since 2015.
Elizabeth Ingram, the newest member of the commission who started her term last month, said she’s still a “newbie,” but didn’t see the harm in considering other proposals.
“I don’t think it hurts to see what else is out there, maybe we’ll still go with them, but I think I would like to put it out for bid,” she said.
Commissioner Warren Lindsey agreed.
“I think that Kurt and your firm have done a fantastic job, but I agree with Commissioner Ingram … if we bid it out very likely [we] could select Fishback again, but I think it’s a conscientious thing for us to do that,” he said.
DeCiccio and commissioners Craig Russell and Kris Cruzada voted in favor of keeping Fishback and approved its requested increase to its hourly rates.
The commission, which spends between $500,000 and $650,000 a year on the city attorney contract, will pay $325 an hour for lead attorneys, up from $275.
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