by Beth Kassab | Feb 1, 2025 | City Commission, News, Uncategorized
In first 'State of the City,' Mayor Sheila DeCiccio highlights strong financials
The annual event drew a large crowd and also honored Winter Park’s employees of the year, including a school resource officer from Winter Park High
Feb. 1, 2025
By Beth Kassab
Mayor Sheila DeCiccio underscored the city’s solid financial footing and pointed to a future of business growth and enhanced services such as flood prevention and the completion of the undergrounding project by the city’s electric utility in her first State of the City address on Friday.
DeCiccio, who made history last year when she was elected as the first woman to the office, spoke to a packed crowd at the Winter Park Events Center, including local officials such as U.S. Rep. Maxwell Frost and state Rep. Anna Eskamani, who recently announced her bid for Orlando mayor.
She highlighted Winter Park’s strong financial position with growing residential and commercial tax bases and a robust reserve fund as part of the city’s $214.4 million annual budget.

Mayor Sheila DeCiccio and City Manager Randy Knight shake hands on stage Friday morning as commissioners Todd Weaver, Marty Sullivan and Craig Russell look on.
“We’ve kept our millage rate the same for 17 consecutive years and we have the strongest tax base in all of Orange County,” she said, pointing to AAA ratings by Fitch and Moody’s.
Fitch upgraded the city to AAA in August citing, “financial resilience given amble budgetary flexibility and Fitch’s expectation that the city will maintain reserves at or above 10% of spending.” The reserve fund sits at about 29% today, just below the city’s goal of 30%.
DeCiccio listed the recent expansion of the Community Redevelopment Agency, which allows Winter Park to keep more dollars that would otherwise be siphoned off to Orange County, as a way the city will shape development and increase tax revenue off Fairbanks Avenue near Interstate 4.
She also cited the undergrounding of electric wires, which sits at 80% completion and is slated to be finished by 2030 as a key factor in how Winter Park has kept the lights on during storms while other communities sat in the dark and lauded a year-long study that has helped prioritize flood-prevention projects.
DeCiccio gave credit to the city’s staff, which she said routinely pull off a number of events that make Winter Park a regional draw.
Last year’s holiday decor and events were just one example.
“It was said it was like being in a Hallmark movie,” she said.
Earlier in her address, DeCiccio nodded briefly to the less feel-good side of Winter Park. The town of about 30,000 people along a picturesque chain of lakes is also known for bitter political fights over everything from development to gas-powered leaf blowers. (A ban on the noisy machines will appear on the March ballot along with two candidates for Commission Seat 3.)
“Our shared commitment to unity and nonpartisan government has allowed us to rise above divisiveness,” she said.
Defense attorney Warren Lindsey, who was just elected to City Commission Seat 4 without opposition and will take office in March, was in attendance. Also in the audience was Justin Vermuth, the attorney and timeshare lobbyist who is challenging Commissioner Kris Cruzada for Seat 3.
Other highlights included:
Founders’ Award. DeCiccio recognized former Mayor David Strong with the 2025 Mayor’s Founders’ Award for his role in steering the city during the 2008 recession and helping protect Central Park from development from a proposal to build a hotel there. Strong, a third generation Winter Parker, whose dad was also mayor in the 1980s, entered the real estate business after graduating from Winter Park High and Vanderbilt University, where he received a football scholarship. DeCiccio also cited his work on Howell Branch Preserve, Casa Feliz and numerous philanthropic activities such as supporting local arts and museums. (Full disclosure: Strong is also a financial contributor to the Voice.)

Officer Christopher Belcore speaks to the crowd.
Employees of the year: Police Chief Tim Volkerson named Christopher Belcore, a school resource officer at Winter Park High School, as officer of the year. Belcore, he said, has served at the school for two years and received numerous accolades from parents about his ability to establish an authentic relationship with students while also leading key investigations. Belcore’s work was instrumental, Volkerson said, in the conviction of a student who Belcore learned had access to weapons and could have posed a threat to the school.
Winter Park Human Resources Director Pam Russell also recognized Jeanni Ruddy, who has helped grow the department’s wellness programs, with the 2025 honor. Winter Park Fire Chief Dan Hagedorn named Lt. Brandon Williams, who is also a paramedic, as fire employee of the year.
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by Beth Kassab | Jan 29, 2025 | City Commission, News, Taxes
Winter Park Police to start new program aimed at helping homeless
The program relies on a federal grant that was temporarily frozen by the Trump administration this week, but Winter Park said it had planned to move forward anyway
Jan. 29, 2025
By Beth Kassab
Winter Park will launch a new program on Monday supported by a federal grant aimed at helping its police department connect homeless people with resources to find housing and other services.
The three-year $250,000 grant through the U.S. Department of Justice’s Community Oriented Policing Services office is slated to fund a portion of two new sworn officer positions at the Winter Park Police Department dedicated to one-on-one interactions with people who are living on the street.
The status of the money was in jeopardy this week as the Trump administration issued a freeze on all federal grants, though Winter Park officials said they planned to move forward anway.
“We have every intention of moving forward with the HART [Homeless Advocacy Response Team] program on Monday, even with the grant freeze,” Winter Park Police Chief Tim Volkerson said Wednesday morning.
By Wednesday afternoon, the administration rescinded the federal memo that froze trillions of dollars, but not before there was widespread confusion and upheaval.

Chief Tim Volkerson
City Manager Randy Knight said he met with U.S. Rep. Maxwell Frost’s office to get a better understanding of the impacts of the freeze, but there remained a number of unanswered questions. The grant for the police department is the primary piece of federal funding in the city’s current operating budget, he said.
The Winter Park program illustrates how the federal freeze trickled down to local jobs and neighborhood programs aimed at helping people in crisis.
It also showcased how local governments like the city of Winter Park, which are tasked with everything from sweeping streets and approving new development to providing lights and water to thousands of homes, are also caught in the crossfire of an increasingly combative and unpredictable political environment on the state and federal levels.
\Winter Park Police not only felt the effect of President Donald Trump’s attempt to root out federal expenditures that he says don’t align with his political ideology, but also must contend with a new state law that bans camping on public property.
The Florida law — which is modeled on policy from the conservative Texas-based Ciero Institute and has also taken hold in Oklahoma, Texas, Kentucky and elsewhere — allows cities like Winter Park to be sued beginning this month if the city doesn’t enforce the ban on sleeping in public areas. It’s one of a number of state laws in recent years that has mandated new action or pre-empted existing policy by local governments, who often carry the biggest burden when it comes to carrying out policy forged in Tallahassee.
Volkerson said his goal is not to arrest people who are homeless, but to connect them with meals, a change of clothes, a shower, medical care and, when possible, permanent housing.
“While the law has changed, our function hasn’t changed,” he said. “Our parks are closed at night and that’s still the case. We want people to know we have these services available and we are more than happy to take you … we ask what they need.”
The HART program, which his officers piloted for a few months last year, is intentional about establishing a rapport with people who are in need. The same two officers are assigned to the duty each day and they drive pickup trucks rather than patrol vehicles.
The pick-up trucks are marked, but have regular back seats compared to patrol vehicles, which are outfitted to transport people who are under arrest.
That makes it more likely, Volkerson said, for people in need to accept rides to drop-in centers, shelters or other places where they can find resources. Usually, he said, that doesn’t happen the first time officers talk with someone. It often takes multiple interactions to build up trust so that a person is willing to consider some of the nonprofits that provide assistance.
“Our goal isn’t to take them and dump them. Our goal is to get them the help that they need,” he said. “Ultimately, we want to connect them with something that is sustainable … there are some people who have no desire for permanent help. They are not interested in going to a shelter or connecting with family and friends.”
His officers have not arrested anyone for sleeping in a public space. Most arrests of people who are homeless, he said, are a result of an officer finding the person has an outstanding warrant on other charges.
“We do not see a lot of sleeping in our parks or on our sidewalks,” Volkerson said. “It’s not that common for us to encounter that.”
Most of the interactions take place on private commercial property such as at gas stations or shopping plazas.
He said his officers focus not just on building relationships with people who are homeless, but with agencies in Central Florida that provide support so that the officers can offer the best options to people who want help with qualifying for social security, Medicaid, a new ID or even just a shower and a hot meal.
The federal grant is expected to cover $250,000 over three years. The city of Winter Park is contributing about $280,000 to cover the cost of the trucks, equipment and the difference in wages and benefits that the grant would not cover.
Frost said the freeze of the grant money was akin to an attempted “theft” from local taxpayers.
“This is political posturing the president is doing on spending to free up money so he can pass it along in the form of tax cuts to billionaires and corporations,” he said. “There’s also just the gross incompetence of how it’s being done and the lack of clarity and confusion it’s causing.”
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by Beth Kassab | Jan 22, 2025 | City Commission, News, Zoning and Development
Dispute over lake view comes down to single palm tree
The commission also applauded the service of Jeff Briggs and heard an update on the negotiations over school resource officers
Jan. 22, 2025
By Beth Kassab
Jeff Briggs, retiring planning director, received a standing ovation Wednesday from the City Commission and those in the audience as he capped 47 years at the city of Winter Park.
Briggs, who is officially retiring this month after a year-long consulting stint with the city, is known for helping to define Winter Park’s unique look and feel through 11 mayors and 32 commissioners.

Jeff Briggs speaks to the commission chambers as Mayor Sheila DeCiccio looks on.
He said Wednesday marked his 1,126th City Commission meeting and joked, “How much suffering can one person take?”
Briggs thanked the commission and the city staff and noted that planning and development tends to be the most controversial topic in the city, an observation that was evidenced later in the meeting when he defended — and the commission upheld — one of his final acts on the job — enforcing landscaping conditions on a lakefront homeowner who neighbors said is detracting from their own water views.
Can a palm tree block a lake view?
The debate over landscaping on Virginia Drive recieved the most air time Wednesday with commissioners ultimately denying an appeal from a homeowner who argued his palm tree did not violate a condition by the Planning & Zoning Board to keep landscaping under 6 feet. The special conditions came about for the property in 2021 when the P&Z board allowed the homeowner to construct his home closer to the lake shore than typically allowed.
Hedges on the property line are also taller than 6 feet, but the homeowner said he would shorten those if he can keep the palm tree in question.
A neighbor two doors down says the tall palm shoots straight through the wider view of Lake Virginia from near the lake’s southeast tip where the shoreline bends around into a small cove.
Michelle Randolph said if someone holds a finger directly in front of you, yes, you can see around the finger.
“But how much of a distraction is the finger?” she asked. “It definitely impairs the view.”
Homeowner Jonathan Cole and his attorney argued that he never agreed to the conditions and that the impact of the tree is minimal, particularly for neighbors who are two doors down. They also argued that the part of the city code that relates to lake views only covers buildings, not landscaping.
“I’ve tried to be neighborly … I’ve tried to have discussions,” Cole said in response to Commissioner Craig Russell, who asked if neighbors tried to simply work out an agreement among themselves. “I’m shocked that I’m here talking about palm trees.”
Ultimately, the commission voted 5-0 to uphold the P&Z decision that the palm tree should be removed.
SRO negotiations continue
City Manager Randy Knight told the board that the city and Orange County Public Schools continue to negotiate a new price tag for the city-provided school resource officers.
He said the cities that did not agree to the districts terms are making progress in moving toward a new deal that would go into effect at the start of next school year.
OCPS, the 8th largest school district in the nation, pays the city about $72,000 a year per officer. That agreement is set to expire at the end of this school year.
Winter Park — along with Apopka, Ocoee, Winter Garden and Windermere — say that’s not enough to cover the true cost of supplying officers to the schools such as health insurance and benefits, the pension fund, equipment and overtime.
The Winter Park Police Department provides officers for Lakemont and Brookshire elementaries and Winter Park High School’s main campus and ninth grade center.
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by Beth Kassab | Jan 21, 2025 | City Commission, Election, News, Uncategorized
Warren Lindsey walks into Commission Seat 4 without opposition
Incumbent Kris Cruzada draws opponent Justin Vermuth for Commission Seat 3 as qualifying ended Tuesday ahead of the March election
Jan. 21, 2025
By Beth Kassab
First-time candidate and local defense attorney Warren Lindsey was automatically elected to the Winter Park City Commission on Tuesday after no other candidates qualified by the noon deadline.
Lindsey will take Seat 4 in the place of Todd Weaver after a swearing-in ceremony set for late March. Weaver opted not to run again.
He said he looked forward to getting to know more city staff and preparing to start his term.
“The polestar of my service will be to always put the interests of our citizens first and to promote our local businesses,” said Lindsey, a registered Democrat, on Tuesday afternoon.

Kris Cruzada
City elections are technically nonpartisan, but party politics historically bleeds into the campaigns and, in turn, some city issues with local party officials providing funding and campaign help.
Records show Lindsey raised nearly $35,000 for his campaign, including a $20,000 loan from himself. Contributors included prominent Democratic donors such as former Mayor Phil Anderson and Jennifer Anderson and former Commissioner Sarah Sprinkel, also a registered Democrat.
Lindsey currently serves on the city’s Planning & Zoning Commission and played a role in pushing Rollins College to agree to make partial tax payments on an apartment project the liberal arts school proposed as a way to provide a more affordable housing option close to campus for its early career faculty. In August, the City Commission approved the project, including the first-of-its-kind PILOT or payment in lieu of taxes agreement between the city and a tax-exempt nonprofit, after multiple revisions to the apartments’ architecture.
“I thought that project represented a constructive and collaborative effort by the city, Rollins and the surrounding neighbors,” he said. “It resulted in a quality project with less density and more parking than originally proposed.”

Justin Vermuth
Joining Lindsey on the dais for a new term in March will be the winner of a two-way contest for Seat 3 between incumbent Kris Cruzada, an attorney, and newcomer Justin Vermuth, an attorney who works as a lobbyist for the timeshare industry. The election is March 11.
Cruzada, a Republican who was first elected to the commission in 2022, grew up in the area and said he wants to continue to serve the residents for another term to “focus on infrastructure, keep our milage rate low and partner with nonprofit institutions on arts and culture,” among other issues.
“Between 36 months ago to today, I’ve learned a lot,” Cruzada said. “I think the record of the commission with Seven Oaks Park, the redevelopment of Winter Park Village, the redevelopment of the former Bank of the Ozarks property has all laid a good foundation for how we would like to develop moving forward.”
Records show Cruzada has raised $1,700.
He said he doesn’t know Vermuth well, but did appoint him to the Lakes and Waterways Board in 2022.
“I look forward to hearing what he has to say and I hope it’s a collegial race where the residents will have the ability to fully discern and decide who will be best for the city of Winter Park,” Cruzada said.
Vermuth did not return messages seeking comment for this story. Because he just entered the race he has not yet filed a campaign finance report. His LinkedIn profile lists him as the senior vice president for government affairs for the American Resort Development Association, which represents the timeshare industry.
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CORRECTION: This story previously listed the wrong party affiliation for former Commissioner Sarah Sprinkel. She is a registered Democrat.
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by Beth Kassab | Jan 9, 2025 | City Commission, Historic Preservation, News
New fines for historic preservation demos delayed
The commission also decided against a mail-only vote on gas-powered leaf blowers and recognized the Winter Park High volleyball team as state champs
Jan. 9, 2025
By Beth Kassab
The City Commission put off for 60 days a decision on new penalties for historic properties that are demolished without approval after residents spoke out against the new rules and called for more opportunities to give input.
Speakers included Charlie Clayton, who owns a construction company involved in the unauthorized demolition of 965 Lakeview Drive in the historic College Quarter neighborhood, which is bordered by Rollins College and Lake Virginia.
He stepped to the podium and referred to himself as the “scourge who created this” and called for additional workshops about the new rules before they are put into place.

A photo from the Orange County Property Appraiser shows how the home at 965 Lakeview Drive looked in 2023. The above image shows what the home looked like last year after demolition.
Winter Parkers have long tussled over historic preservation rules with some in the camp of preserving the architectural contributions of often smaller homes built 50 or 100 years ago and others looking to maximize square footage on high-priced lakefront lots and other valuable property with more modern builds.
Suzanne Brandon, who lives in College Quarter, said she was in favor of the new rules to preserve the neighborhood, but also asked for more communication with the residents.
“I am in favor of this … we do need the 30% fine to prevent developers from bypassing the historic preservation board,” she said. “We need to make sure what is being built maintains the historic aesthetic.”
Mayor Sheila DeCiccio expressed disappointment that over time the rhetoric turned “nasty” and caused “divisiveness.” She noted that people move to Winter Park because of its charm and the unique historic homes that add value to the city — “that’s what keeps our housing prices so high.”
She supported a 60-day pause on the new rules and fines to allow staff to hold a workshop with historic home owners and other interested residents to provide more feedback on the changes.
No mail-only vote for leaf blower question
After urging the commission to move to a mail-only ballot for upcoming vote on whether the city should keep its ban on gas-powered leaf blowers, City Manager Randy Knight on Wednesday put a halt to that concept.
Turns out, he said, that a mail-only ballot would cost the city an additional $20,000 or so compared to an in-person vote.
As a result, commissioners opted against moving to the mail-only method if the two seats up for grabs on the commission remain unopposed by the Jan. 21 deadline. The election will be held March 11.
Good news for Winter Park Playhouse
The board gave official approval for a contract to by the building occupied by the Winter Park Playhouse. The nonprofit professional musical theater has spent nearly two years trying to secure a home after the building’s owner decided to sell and told the group it would lose its lease.
The deal is made possible through an $8 million grant from county Tourist Development Tax dollars. The Playhouse has pledged to raise $2 million toward the project.
“I hope you are able to hear the applause that erupt at the playhouse every time we announce that we will be able to stay at our location,” playhouse board member Judith Marlowe told the commission.
Volleyball team recognized as state champs

Winter Park High Volleyball is honored Wednesday at the City Commission.
Commissioners took a moment on Wednesday to celebrate the Winter Park High School volleyball team, which won the state title in November, it’s sixth championship in the program’s history.
“We played the toughest schedule we could find,” said Coach Stephanie Gibson, who was recognized last month as Florida Dairy Farmers girls volleyball coach of the year, making her what the Orlando Sentinel called a “36-year legend and the first coach to claim that honor five times.” “I’m so proud of the work we do on the court, probably the more impressive thing is each and every athlete also received” honors related to their academic performance.
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