by Beth Kassab | Oct 2, 2026 | News, Taxes
Maxwell Frost and Sheila DeCiccio hear from Winter Park residents on SunRail, Amendment 3 and More
At a town hall held at Mead Botanical Garden this week residents also asked about everything from AI policy to Tourist Development Taxes
Oct. 2, 2026
By Gabrielle Russon
On a Friday in March, more than 12,000 passengers rode SunRail to and from Central Park to visit the Winter Park Sidewalk Art Festival.
But that weekend, the SunRail shut down like normal for the remainder of the festival. No trains ran, no matter how much Winter Park officials wanted them.
“We beg them. We will pay you. Can we please have it on the busy weekend?” Winter Park Mayor Sheila DeCiccio said. “Wouldn’t that be great for Winter Park?
The answer — still an emphatic “no.”
Now, DeCiccio said she is “leading the charge with the mayors in Central Florida to ask the Legislature to change the law and free up the hundreds of millions of Orange County hotel tax revenue to help fund public transportation.
DeCiccio and U.S. Rep. Maxwell Frost held a 90-minute town hall Thursday night at Mead Botanical Garden to listen to residents’ concerns and talk about the citywide issues, including parking, traffic and a lack of public transportation.
One resident asked if it was a good sign that SunRail got special late-night weeknight trains to transport theater-goers seeing “Hamilton” this month at the Dr. Phillips Center for the Performing Arts.
“I hope so,” DeCiccio said as she said she keeps working on expanding weekend SunRail service.
Winter Park is a regional tourism destination with a thriving Saturday farmer’s market, weekend Track Shack running races and beloved holiday traditions in the downtown that draw thousands. And the city’s train station allows passengers to hop on and off the rail from the center of most of the action: Central Park.
“Really it should run all weekend because there’s so many people that come in and out,” the mayor said.
DeCiccio sent letters to other local mayors urging them to join the fight in reforming the 6% hotel tax which is also known as the tourist development tax (TDT).
Frost, who represents the city of Winter Park in Congress, also called transportation one of his top priorities. He expressed support for using TDT money for transportation but said he hopes federal funding from an infrastructure package emerges after the November election when Democrats are predicted to make up ground in Washington, D.C.
The lack of public transportation “is really holding us back” and preventing Central Florida from attracting large-scale events and helping tourism workers get to their jobs, Frost said.
US Rep. Maxwell Frost and Winter Park Mayor Sheila DeCiccio speak to residents on Oct. 1 at at town hall at Mead Botanical Garden.
At Thursday’s town hall, other residents used their moment of face time with the two elected officials Thursday to complain about Winter Park’s brick streets, express their fears about the threat of artificial intelligence and ask about other issues.
Don’t hold your breath for any immediate federal laws to protect humanity from AI.
“I’m going to be honest with you guys. Part of the problem is Congress lacks the expertise and technology to be able to move forward and pass real comprehensive legislation,” Frost said.
Dominating Thursday’s discussion was Amendment 3 as both DeCiccio and Frost expressed their concerns about the constitutional amendment to increase non-school homestead exemptions.
Amendment 3 is the latest threat to local governments after the state has been eroding away at local home rule for years, they said.
“We had an ordinance you couldn’t just take down a big beautiful oak or tree in your yard,” DeCiccio said, citing an example of how the state is superseding Winter Park’s authority to make decisions. “We love our trees. It’s part of our charm. It’s part of our character. It keeps us cool.”
Instead Tallahassee passed a 2022 bill allowing people to cut down a dead or dying tree without a local permit which developers are taking advantage of to remove trees, DeCiccio said.
Local governments losing millions of revenue would be forced to ask Tallahassee for approval and funding.
“They’re trying to push our local governments to have to go to Tallahassee and beg for crumbs and money to be able to do anything. And that’s about power,” Frost said.
DeCiccio warned the city would be forced to close the library “a few days a week” and its police and fire response times would get slower. Also potentially getting cut would be city festivities in the park to celebrate holidays, “all of the things that make Winter Park so very special,” she said.
One resident asked how people can get involved to help defeat Amendment 3.
“One thing is to have conversations with people in your neighborhood,” said Frost, whose political career started as a community organizer. “You know who are the homeowners, who are the tenants. Reach out to a neighbor and talk to them about it. … If everybody in this room spoke with 20 people between now and Election Day, that could literally mean the difference between it passing and it not passing.”
If at least 60% of voters approve the Amendment 3 on Nov. 3, the constitutional amendment would increase the state’s non-school homestead exemptions to $150,000 in 2027 and $250,000 in 2028, and tie further increases in 2029 annually to inflation.
New Florida residents would be required to wait five years to get the full property tax break.
Under Amendment 3, Winter Park City Manager Randy Knight previously said the city would need to cut an estimated $3.7 million in the first year, followed by another $7.5 million the second year.
The Florida Realtors, which spent $10 million on its Vote Yes on 3 political committee last month, are the loudest advocates for Amendment 3, along with conservative state lawmakers and Gov. Ron DeSantis who have been calling out for property tax relief for months.
Real estate agents make their livings off commissions from home sales and a report published on Realtor.com asserted that eliminating property taxes on owner-occupied homes would increase prices by 7% to 9%. In turn, such a move would also juice commissions for Realtors.
“Florida families are facing rising costs from every direction, from housing and insurance to groceries and everyday necessities. Amendment 3 provides meaningful property-tax relief at a time when many homeowners need it most,” said the Florida Realtors in a statement this week.
Meanwhile, the Florida Sheriffs Association, the Florida State Fraternal Order of Police and the Florida Professional Firefighters have come out strongly against Amendment 3 with the groups saying it could have the opposite effect by eating into the appeal of safety and other amenities provided by local governments that make many neighborhoods so desirable.
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by Beth Kassab | Sep 30, 2026 | Chain of Lakes, City Commission, News, Zoning and Development
New Merrywood Owner (Who is Still Unknown) Will Pursue Lot Split
A second vote on the property that is known as the site of a large James Gamble Rogers II estate is scheduled for Oct. 14
Sept. 30, 2026
By Beth Kassab
One of Winter Park’s most closely guarded secrets — the identity of the new owner of the lot known as Merrywood at 1020 Palmer Ave. — may soon be revealed.
Jason Searl, a real estate attorney at Maynard Nexsen, sent a letter to Winter Park Planning Director Allison McGillis on Sept. 23 saying he was recently hired to represent Lake Osceola Holdings LLC, the entity that closed on the nearly 4-acre property in August for $15 million, and that the new owner is seeking to complete the process needed to split the lot in two.
“My client desires to continue with the pending Comp Plan Amendment and will accept responsibility for the application going forward,” Searl wrote.
The second of two required City Commission votes to finalize the change to the city’s development plan, which would carve out a special exception to Winter Park’s prohibition against lakefront lot splits for Merrywood, is scheduled for Oct. 14.
McGillis told the Voice she does not know who is behind Lake Osceola Holdings LLC, but said Searl indicated to her in a conversation that the new owners would likely meet with commissioners or potentially appear at the public meeting. That could mean they would be identified and potentially discuss their plans for the property.
She said she does not have any details about the owner’s plans, but said she was told it was possible that some portion of the 90-year-old estate on Lake Osceola could be preserved. The house is listed in Florida’s master file of historic resources and is among the last remaining examples of the local influence of architect James Gamble Rogers II, and is known as one of his largest and most ornate works.
Tara Tedrow, the Lowndes attorney who originally had the property under contract and began the lot split process last year, was copied on the email thread that included Searl’s letter and followed up with her own note indicating that she would no longer be involved in the process.
“Please accept this email as written confirmation of a transfer of my pending comp plan application to Lake Osceola Holdings, LLC,” Tedrow wrote.
McGillis requested the correspondence from both Tedrow and Searl so that she could meet the deadlines for public notice ahead of the Oct. 14 scheduled vote.
Neither Searl nor Tedrow responded to requests for comment from the Voice on Wednesday.
Lake Osceola Holdings LLC filed its articles of incorporation with the state of Florida’s Division of Corporations on June 10. It listed Carla Deloach as the manager of the company, and its Orlando address is the same as Cypress Row Advisors, where Deloach is a senior attorney.
On that same date, Tedrow filed with the state a company called Ketara RE LLC and listed herself and her husband, Kevin Skorman, as the managers.
June 10 fell about a week after the Planning & Zoning Board recommended that the City Commission approve the lot split, and about two weeks before the first hearing related to the property in front of the City Commission.
Tedrow did not respond to questions about whether the company she registered on June 10 was related to the lot on Palmer Avenue. She is also listed as a manager, along with Skorman, a local commercial and residential developer, on three other companies filed with the state between March and September.
Tedrow told city officials throughout the process that she hoped to build a home for her family on the empty portion of the Merrywood lot, which is not far from the house she grew up in, and sell the other portion.
She told the City Commission that she and Sotheby’s agent Mick Night hoped to find a buyer willing to preserve and restore Merrywood, which is now in disrepair, but that no one came forward after nearly a year of searching.
That led Mayor Sheila DeCiccio to say that there was little choice but to approve the lot split, because the house was likely to be demolished either way, and Tedrow said she would walk away from the deal if the split wasn’t approved. DeCiccio said she feared that without the split, another buyer would come along and build a house as large as 50,000 square feet, based on the entitlements related to the size of the lot. As a result, the City Commission voted 3-2 on June 24 in the first of two required votes to approve the split.
Not long after that, the Voice first reported that Matt Morgan, a Winter Park resident and key face of the Morgan & Morgan law firm, made an offer on the property in August 2025 for $10 million. Night said the offer was too low and that, at the time, he was unaware of Morgan’s desire to preserve the home.
Morgan, who currently lives in a home on the city’s historic register, then upped his offer to $12 million and said he would like to see Merrywood preserved.
The city extended a demolition permit for the property in August. City officials have little power to require the home be preserved because its longtime owners, before the most recent sale, never listed it on the local register.
The clearest path to keep the home standing is for the City Commission to approve the lot split with a condition that the home remain in place and be listed on the register — similar to a condition placed on a different property in recent years, in a case where the owner was also seeking to split the lot.
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by Beth Kassab | Sep 28, 2026 | City Commission, News, Police and Public Safety
Winter Park Suspends Flock Cameras for At Least 90 Days
The police department said the cameras are a beneficial tool for solving crimes and would like to reinstate them once a new policy is finalized
Sept. 28, 2026
By Allison Smith
Winter Park Police Chief Tim Volkerson confirmed that his agency’s Flock cameras and any other automatic license plate readers (ALPRs) are no longer in use following a suspension of the program approved by the City Commission last week.
The suspension will run for at least 90 days, giving the department time to “assess and discuss” the changes needed to protect the privacy of law-abiding residents and guard against potential abuses by law enforcement, while still reaping the benefits the cameras provide as investigative and crime-solving tools, he said.
“We’ve made policy changes to try and keep up with putting appropriate guardrails on [license plate reader] systems,” Volkerson told the commission. “But it’s a very fluid thing … And honestly, I feel like a dog chasing my own tail, trying to keep up with everything.”
In August, Volkerson updated his department’s policy to more strictly limit how the camera database can be used, in response to incidents of police abuse elsewhere. In Haines City, about an hour southwest of Winter Park, a police officer was arrested and charged with official misconduct and other computer-related crimes. The officer allegedly used the Flock system for more than 700 searches over about two years to track the whereabouts of his estranged wife’s vehicle.
“We’re banning any of those features that create more of the feeling of distrust in the community,” Volkerson said.
A camera appears on a utility pole near a church on Howell Branch Road in Winter Park. (Photo by Allison Smith)
However, he said he needs until at least early 2027 to determine what the full policy should look like going forward.
Commissioner Warren Lindsey expressed concern that the Florida Legislature could override whatever new policy the city comes up with when lawmakers meet again in March. In recent years, the Legislature has repeatedly preempted city and county rules, chipping away at local governments’ ability to govern themselves with one-size-fits-all solutions for the entire state.
Volkerson said he plans to stay in touch with lawmakers and address their concerns, and he hopes to have a policy in place before the annual legislative session begins in March.
Winter Park signed a 60-month contract with Flock Safety in 2023 for three cameras at a cost of $7,500 a year, according to the contract.
All three cameras were positioned on state-owned roads. They were deactivated after the Florida Department of Transportation revoked permits for such devices across the state in August.
Winter Park also uses cameras manufactured by Motorola Solutions, which primarily sells to government agencies and law enforcement, according to the company’s public financial filings. Those cameras are also included in the citywide suspension and will be subject to the new policy.
Volkerson declined to comment on how many Motorola cameras were recently in use, but said they were acquired through a grant.
Using the popular crowdsourced site Deflock, a Voice reporter attempted to photograph ALPRs in and around Winter Park. The Voice confirmed the locations of 13 cameras listed on the site’s interactive, open-source map.
Some of the cameras are on private property, such as the campus of Rollins College.
One camera on a median on Horatio Avenue near Howell Branch Road in Maitland appeared to be covered with a garbage bag.
A bag appears over a camera in Maitland on Horatio Avenue. (Photo by Allison Smith)
Volkerson said he expects the state to begin fining agencies for misuse of ALPR systems, similar to the penalties for abuse of another law enforcement database, the Driver and Vehicle Information Database, known as DAVID. That database contains Florida driver’s license numbers, home addresses, photos, signatures, birth dates, vehicle information and more. DAVID has also been prone to misuse by law enforcement and other officials over the years, and its rules could serve as a model for Flock technology.
“Protecting people’s privacy is extremely important,” Volkerson said. “Any violation of that is an extremely serious offense.”
According to the department’s ALPR policy, updated in August, the database can be used only for active investigations, and information cannot be shared with anyone who is not directly involved in the investigation.
The cameras use optical recognition technology to check license tags against a so-called “hot list.” They provide a visual and audible alarm when a tag matches lists of stolen vehicles, suspended driver’s licenses, registered sex offenders, registered felons and other local intelligence pertaining to gang or drug investigations, according to a copy of the policy.
An APLR camera appears on the first floor of the Truist Parking garage just off Park Avenue in Winter Park. (Photo by Allison Smith)
Officers in Winter Park can manually add to the hot lists only in certain circumstances, such as a new Amber or Silver Alert, license plates related to wanted or missing persons, and those necessary for “gathering criminal intelligence during an active investigation.” Searches can be traced to the officer’s name and case number, and officers must enter a reason for each search.
Volkerson said the department still needs to determine a retention period for the images and information the cameras collect, along with rules for cameras near sensitive areas such as schools, health care facilities and churches.
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by Beth Kassab | Sep 19, 2026 | City Commission, News
Amendment 3 would bring property tax cuts — and tough choices — to Winter Park
City Manager Randy Knight said during a Winter Park Chamber forum that the city could ‘survive’ the cuts, but warned they would come with painful budget trade-offs
Sept. 19, 2026
By Gabrielle Russon
Winter Park government will “survive” if Amendment 3 passes in November, although City Manager Randy Knight warned that property tax cuts would not come without “pains.”
In the first year, the city would need to axe an estimated $3.7 million from a $90 million budget, followed by another $7.5 million the following year, which Knight called “doable.”
But when the city conducted an exercise last month to practice eliminating nonessential services, such as wintertime pool access, Knight quipped, “You would’ve thought we had canceled Ted Lasso.”
Knight was part of a trio of speakers who expressed concerns about Amendment 3 during Friday’s Winter Park Chamber of Commerce panel, held in front of business and community leaders. Joining Knight were Orange County Tax Collector Scott Randolph and Florida TaxWatch CEO Jeff Kottkamp.
The Winter Park Chamber of Commerce has not taken a public stance on Amendment 3, although other economic organizations, including the Orlando Economic Partnership, have spoken out against it.
Under Amendment 3, a Winter Park taxpayer who receives the maximum benefit would save about $850 in the first year and $1,780 in the second year, which equals nearly $150 a month, Knight said.
TaxWatch CEO Jeff Kottkamp, Orange Tax Collector Scott Randolph and Winter Park City Manager Randy Knight discuss the anticipated impacts of an amendment on the November ballot that would raise the homestead exemption. The Winter Park Chamber of Commerce hosted the forum on Friday.
With those savings come trade-offs, the panel warned.
Knight said Amendment 3 could force the city to raise its millage rate, increasing taxes on renters, businesses and homeowners of more expensive properties to make up for lost property tax revenue.
Local governments may also raise fees, Kottkamp said.
“You may vote for this thinking you’ll get a property tax reduction when, in fact, you won’t,” said Kottkamp, a former state lieutenant governor.
For local governments, the amendment could also have an impact on other fronts if they miss out on federal or state grants because they can no longer provide matching funds, Randolph said.
If at least 60% of voters approve Amendment 3 in November, the constitutional amendment would increase the state’s non-school homestead exemption to $150,000 in 2027 and $250,000 in 2028, with further increases tied to inflation beginning in 2029.
The ballot amendment would also cut local government tax revenues by limiting future growth in the amount of taxes collected on non-homesteaded properties. The cap on annual assessment increases for those properties — anything from a Publix grocery store to an Amazon warehouse to a vacation home — would drop from 10% to 5%.
New Florida residents would be required to wait five years to receive the full increased property tax exemption.
Randolph, a Democrat and former state lawmaker, questioned whether the Legislature’s five-year waiting period for new residents was constitutional because it treats out-of-state and Florida residents differently for tax purposes.
“Look, Florida is built on the idea of attracting new people. I don’t know how you’re supposed to attract a business or attract a young couple or even a retiree coming into this marketplace,” Randolph said. “They’re already going to be paying the highest full market value when they buy the house. And then you’re going to tell them, ‘Oh yeah, you know what? Just for giggles, we’re not even going to give you the $250,000 exemption for five years.’”
The state Legislature voted to put Amendment 3 on the ballot during a three-day special session in June. The vote came without the state conducting any deeper economic impact studies to understand the consequences of overhauling property taxes statewide.
“When you have something this important, the way this was done was just not right. You don’t drop a bill and say, ‘Vote on this in three days,’” Kottkamp said.
State lawmakers acted after facing pressure from Gov. Ron DeSantis, who had been calling for property tax reform to lift the burden on residents struggling with rising costs. DeSantis has argued that people who have already paid off their homes are unfairly hit with rising property taxes and that local governments’ budgets are ballooning with wasteful spending.
DeSantis also expressed disappointment that Amendment 3 doesn’t go far enough to reduce school taxes because state lawmakers protected school funding in their ballot proposal.
Meanwhile, critics question whether Amendment 3 is another move by the state to take more control away from local governments, which set their own spending priorities.
Randolph called it “absurd” to say current homeowners are being “taxed out of their home” because the state’s Constitution already contains an amendment capping the annual increase in the assessed value of a homesteaded home at 3%, or the Consumer Price Index, whichever is lower.
But the ones “getting killed” by property taxes are new homeowners who purchased homes in the past five years, Randolph said.
“This amendment doesn’t fix that at all,” Randolph said. “And that’s what I wish Tallahassee would focus on — the fairness and the equity across the board — because if property taxes are supposed to reflect the services that are provided, we have shifted so much of that to the new entrants into the market.”
Instead of Amendment 3, Kottkamp is advocating for the state to make changes after the Florida Taxation and Budget Reform Commission meets next year. The commission, which convenes every 20 years, could develop a more thoughtfully laid-out proposal to reduce property taxes, he said.
In a conversation where all three panelists expressed skepticism and concerns, the most optimistic sentiment came from Kottkamp, who offered this assessment of Florida:
“This is still the greatest place to live and do business in the country, which means in the world. We just want to make sure we keep it that way,” he said.
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by Beth Kassab | Sep 15, 2026 | Chain of Lakes, News
No Paid Parking at Dog Park After All
The park at Lake Baldwin was slated to be part of a pilot project to charge non-residents for parking
Sept. 15, 2026
By Beth Kassab
An agreement between Orlando and Winter Park unearthed from 24 years ago means the city of Winter Park can no longer move forward with plan to charge non-residents to park at the dog park on Lake Baldwin, City Manager Randy Knight said late Tuesday afternoon.
The agreement, he said, requires that residents in Orlando and Winter Park have equal access to two parks — one controlled by each jurisdiction — along the lake bordered by both cities.
“If the pilot program went forward at Lake Baldwin Park, Orlando residents would need to be exempted from the parking fee the same as Winter Park residents, which administratively would be a larger undertaking,” Knight said in a news release announcing the update. “As a result of this document and input received from citizens, the city is removing Lake Baldwin Park from the Pay for Parking Pilot Program but will continue to move forward with the pilot at Dinky Dock. The technology behind this program is still important important to explore as a tool to manage parking more effectively.”
A view of Dinky Dock on a summer day.
The City Commission approved the six-month pilot program last week as part of a plan to raise more money as well as find a new way to reduce parking snarls in other parts of the city if the trial period is considered a success.
Some details are still not known, such as the exact cost to park at Dinky Dock, which is often busy on the weekends as people from surrounding cities use the dock for jet skis and other watercraft on Lake Virginia.
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by Beth Kassab | Sep 15, 2026 | Arts and Culture, City Commission, News, Taxes
Parking Fines to Increase, E-Bike Fines also added as Budget is Finalized
The City Commission also reduced the amount of money set to go to nonprofit Men of Integrity Mentoring Program and turned down requests to add dollars for the library and Blue Bamboo back into the budget
Sept. 15, 2026
By Beth Kassab
Winter Park will bring in additional revenue next year through higher fines for parking tickets, fees for non-residents to park at Dinky Dock and the dog park at Lake Baldwin, and new fines for kids and adults who violate recently approved rules governing the use of e-bikes and e-scooters.
The City Commission also made last-minute tweaks to the budget that takes effect Oct. 1, reducing the amount of money the nonprofit Men of Integrity Mentoring Program will receive and rejecting calls to restore cuts to the Winter Park Library and Blue Bamboo.
Some details remain unclear, including exactly how much the new fines for parking and micromobility violations could bring in.
The fees for non-residents to park at Dinky Dock and the dog park have not yet been set but could be in the range of $2 to $3 per hour. The pilot program is expected to start later in the year after a company is selected to administer it.
Motorists who park along the curb facing the wrong direction, overstay the allotted time at a curb or otherwise park in an unlawful manner will now face a $30 fine, up from $25.
Commissioner Elizabeth Ingram pushed for even higher parking fines, noting that the discussion occurred during a meeting that lasted more than five hours, with a substantial portion devoted to parking concerns related to a proposal to build a synagogue and daycare downtown.
She said she was “shocked” to learn that parking fines are only $25 and suggested they could be as high as $75 or even $150 to help change motorists’ behavior.
“It doesn’t hurt enough to teach someone,” she said.
City Manager Randy Knight warned that complaints would pour in if fines were raised that high.
“We get complaints about $25 all the time, and so if you go to $75 … maybe you each get to serve as cashier one day a week,” he said in jest.
Police Chief Tim Volkerson said his team issues parking fines every day and noted that Orlando recently raised its fine to $35.
The commission settled on a $30 fine for parking violations.
The group also raised the fines for violating the new micromobility ordinance to $35 for a first offense and $75 for a second offense.
When it came to the portion of the budget — about $480,000 — that the city spends on local nonprofit groups, a proposed $45,000 allocation for Men of Integrity was reduced to $20,000.
Commissioner Warren Lindsey said he wasn’t comfortable with the amount, given that the group is already provided free space at the Community Center and because commissioners are being forced to make some cuts that he called “painful and uncomfortable.”
Men of Integrity serves about 24 boys, including 10 in high school and 14 under the age of 12, said Antwon Carter, the group’s leader. Many of the kids attend Winter Park schools, but some travel from outside the city to attend the weekly program. An administrator for the program provided the Voice with a copy of Men of Integrity’s most recent tax form, which shows that the group’s revenues are typically less than $50,000.
Ingram attempted to restore some funding for Blue Bamboo in response to pleas from one of the group’s leaders but did not win enough support.
Officials from the Winter Park Library also asked the commission to consider restoring a $25,000 cut to its budget but did not win support.
Even with the $25,000 reduction, the Winter Park Library is still slated to receive nearly $50,000 more than last year in support from the city’s main budget and the Community Redevelopment Agency budget, for a total of $2.5 million.
The second required vote on the city budget is scheduled for Sept. 23.
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