Winter Park Contends with Higher Police and Fire Costs and How to Maintain Roads
The city’s proposed 2027 budget is also cautious of future cuts to property taxes if voters approve a measure on the November ballot. Winter Park homeowners would save less than $2,000 a year, but the city could ‘lose some of the things that make it feel extra special’
July 22, 2026
By Beth Kassab
The Winter Park City Commission is poised today to adopt the same property tax millage for the 19th year in a row, but the steady rate belies an increasingly complex financial picture for one of the region’s most high-profile cities as it contends with soaring costs for its police and fire departments, a demand from residents for better roads, increasing prices for electric and water customers and a governor and state Legislature looking to slash property revenues.
The All-Funds Budget, which includes the General Fund as well as the utilities and other funds, is proposed to increase this year by nearly 6% to $247 million. The General Fund, which pays for essential services such as police, fire, parks, public works and administration, is growing by about 5% to $94.6 million.
The growth in money collected by the city is being driven by higher bills for electricity, water and stormwater — the result of policy decisions in recent years and up for debate again this year by a City Commission facing big expenses to prevent storm flooding and to continue to underground all of the power lines for the city-owned electric utility. Property taxes remain a driver of growth in the general fund, where the taxes make up just under half of the revenue pie.
City Manager Randy Knight cautioned that a measure on the November ballot initiated by Gov. Ron DeSantis and the Florida Legislature to significantly alter how local governments are funded by reducing property owners’ tax bills could eat into the kinds of services the city provides by 2028, when it is set to take effect if it passes with the required 60% approval from voters.
City officials are forecasting a hit of at least $5.4 million in the first year. Translated into savings for individuals residents, homesteaded property owners would pay about $818 less per year to Winter Park. The total tax savings per year for Winter Park homeowners if the ballot measure passes would be $1,783, including the reduction paid to the city as well as the reductions in taxes paid to Orange County and St. Johns River Water Management District. (Taxes paid to schools would remain unchanged under the tax proposal on the ballot.)
“It will have an impact on city services that will be felt,” Knight said in his annul budget memorandum to the City Commission. “Winter Park will still be able to provide essential services, but the city may lose some of the things that make it feel extra special … A loss of over $5 million is like losing almost half of the Parks Department, so it will not be a small issue to determine how best to prioritize spending, but it is likely that a combination of service reductions and revenue increases will end up balancing the budget in future years.”
With just six months to go before his retirement after decades at the helm of the city and 36 years since he helped prepared his first budget in 1990 as the city’s finance director, Knight was reflective in his final budget memo of past challenges.
“As we face potential impacts from the so-called tax reform, I want to remind you that we have faced tough times before and always endured,” Knight wrote. “The 2004 hurricane season cost approximately $18 million for recovery and wiped out our reserves. The 2008 housing bubble coupled with tax reform resulted in a huge hit on city revenues. The Pandemic shuttered businesses and locked down communities, but we survived and thrived. Today Winter Park is the envy of the region, with commercial properties with the lowest vacancy rates and highest asking rents, exceptional schools, and beautiful walkable residential communities and amenities. Over 3 million visitors come to the crown jewel of downtown Park Avenue each year and our financial reserves have grown to over $24 million.”
A graphic from Winter Park’s proposed budget document shows how money in the General Fund is spent.
But the budget document also described in stark terms how expenses for basic needs like police and fire are simply outpacing revenues.
Record-high pension costs for police officers and firefighters as well as a new labor contract with the Fire Union that included a 12% pay increase in 2026 will account for 70% of new costs in the proposed 2027 budget.
“Of the $4 million in the increase in personnel wage and benefit costs in the General Fund estimated for the next fiscal year, almost a third (30%) is due to increases in public safety pensions for police and fire
retirement plans,” according to the budget proposal.
The city will have to spend $1.2 million more on the pensions, according to the document, the result of “changes in actuarial tables, the addition of new employees and the weak 2022 stock market year that still affects their formulas.”
“Staff is reviewing the possibility of making adjustments to the pension plan in the future to attempt to mitigate this growing cost,” the document said. “With property tax reform on the horizon, having a quarter of the entire annual growth in revenue going solely to public safety pensions, is not sustainable.”
Police pay has increased by nearly 50% in Winter park in recent years and the proposed 2027 police department budget is $23.2 million, up from $14.9 million in 2020. The department will keep a community services position vacant next year to help reduce some costs, according to the proposal. The city has 121 full-time police staff and three part-time staff slated for 2027, up from 115 full-time staff and 13 part-time staff in 2023.
The budget for the fire department is up from $13.2 million in 2020 to a proposed nearly $19 million for next year. The department has grown from 81 full-time staff and two part-time staff in 2023 to 84 full-time staff and three part-time staff.
Winter Park is not alone in what has amounted to an arms race in public safety pay across Florida as departments have struggled to recruit and keep candidates for jobs that require personal risk, physical stamina and no work-from-home privileges in a post-pandemic world where many offices have emptied out.
For example, the pay for a starting deputy at the Orange County Sheriff’s office in 2020 was $49,296, according to the office. By 2025 it was $62,566. That’s in addition to increases in bonuses, the number of paid holidays and minimum compensation for off-duty pay and longevity pay.
A graphic from the city’s budget presentation shows the potential cumulative effect of the property tax measure on this November’s ballot.
In addition to public safety costs, roads emerged as Winter Park’s other main budget priority this year.
That’s the result of a survey of residents with about 800 responses that identified the quality of both brick and asphalt streets as a major need for improvement.
“This has been an area in which funding has been added in the past, but it has been insufficient to keep pace with the level of street deterioration and the cost of repairs,” read the budget memorandum.
The budget includes more money for contractors to resurface roads and doubles the amount for road materials with an additional $500,000. Winter Park has fallen short of its own goal of redoing 9 lane miles o road each year, typically completing just 4 or 5 lane miles with the exception of in 2025. The new goal will be to achieve repaving of 7.5 lane miles each year.
City Commissioners are slated to vote on the property tax rate this afternoon. More discussion and debate over the full proposed budget is scheduled for August with a final budget vote in September before the start of the new financial year in October.
Winter Park Voice Partners on Upcoming Voters Guide with Local News Outlets
The Voters Guide is the latest project of the News Collaborative of Central Florida, which is endeavoring to work together to bring more people high-quality local news
July 13, 2026
Staff
The Winter Park Voice is partnering with six other local news outlets to create a voters guide for the primary election on Aug. 18 and the general election on Nov. 3.
The project is part of the News Collaborative of Central Florida, a group of independent local news organizations and aligned partners working toward a more informed and engaged Central Florida.
The Voters Guide aligns with the mission of the nonprofit Winter Park Voice, which aims to provide its readers with high-quality reporting about their local government and matters that influence life in Winter Park.
“At the Winter Park Voice, we serve an audience who cares deeply about local civic and political happenings and this collaboration will help us deliver more of the election coverage our readers deserve,” said Winter Park Voice Editor Beth Kassab. “Our regional News Collaborative is still new, and many people are still learning about it, but it’s already showing how our news organizations can combine resources in ways that we hope make a bigger impact than any one of us could make on our own.”
The news organizations collaborated to create questionnaires for candidates in federal, state, county and judicial races to answer. Questions range from asking candidates what are their top issues, how they would address affordability and even where they stand on Florida’s proposed constitutional amendment on property tax reductions.
In the most recent episode of Talking Central Florida, a podcast funded by the News Collaborative, host Steve Mort and Sentinel Executive Editor Roger Simmons discuss the Voters Guide. Pictured is Mort (right) with Donovan Myrie from WKMG News 6, from the same episode, who discussed Florida’s new approach to tax holidays and whether changes adopted by the Legislature in 2025 could have an unintended impact on hurricane preparedness.
The goal is to give more people access to the candidates’ positions in their own words on the topics that matter most to people in Central Florida.
The city of Winter Park doesn’t have any races on the August or November ballots — those occur in March. But voters in Winter Park will play an important role in deciding races for Orange County Mayor, School Board Chair, Clerk of Court, judicial races and the Orange Soil and Water Conservation District on top of this year’s open race for the next Florida governor and other state and federal seats.
“This is the first time we have news outlets in our region cooperating to create a guide to help voters make informed choices at the polls,” Sentinel Executive Editor Roger Simmons said. “It’s really extraordinary to see these newsrooms come together to work on an important project like this.”
Candidates have already been contacted several times to respond to the questionnaire. If a candidate does not respond, it will be noted in the voters guide. The news organizations may then try to answer the questions for the candidates from information posted on campaign sites or social media.
“Of course our preference is for all candidates to answer themselves,” Simmons said, “but it may be telling for voters to see who responded and who did not.”
The goal is for the voters guide to publish by the end of July, in time for early voting and primary election day on Aug. 18.
The News Collaborative of Central Florida was a result of the Central Florida Journalism Ecosystem Summit, created in 2024 by Central Florida Public Media, Central Florida Foundation and Oviedo Community News. Collaborative members worked together last year on a project focusing on the impact of the state’s homeless camping ban.
Commission Approves Contract for Next City Manager Michelle del Valle
Randy Knight will retire from the post in January after 19 years in the role
July 9, 2026
By Beth Kassab
The City Commission this week quietly approved the contract for Michelle del Valle to take over as city manager when Randy Knight retires early next year.
The city will pay del Valle $290,000 a year plus benefits including a $775 monthly car allowance and memberships to two civic organizations or other clubs of her choosing, according to the contract approved without discussion as part of the commission’s consent agenda on Wednesday.
Knight, who has a similar contract, is projected to earn $294,000 a year by the time he leaves the post in January after 19 years in the role and more than 30 years with the city.
Commissioners voted unanimously in April to name del Valle, who has served as assistant city manager since 2008, as his successor. She is projected to earn $263,665 in her current job.
Winter Park has a city manager form of government, which means the person in that job sets the tone and oversees every department — from the $247 million budget to parks to police and fire rescue — helming more than 500 employees. The elected commissioners set policy, but the manager is responsible for overseeing the execution of that policy.
Del Valle is slated to take over the top role in January.
Orange School Board Looking to Ban Electric Scooters and Bikes at Elementary and Middle Campuses
Talk of the proposed ban came this week as cities like Winter Park are attempting to finalize their own micromobility ordinances ahead of the start of the school year
July 9, 2026
By Gabrielle Russon
Orange County Public Schools board members appear poised to ban electric bikes and scooters at elementary and middle schools while only allowing high schoolers with driver’s licenses to ride them.
The board met during a Tuesday workshop to discuss a proposed policy as cities like Winter Park are also crafting new rules aimed at stopping more crashes from happening. The school board did not take any action Tuesday but could vote on the final policy at a July 28 meeting ahead of the 2026-27 school year in August.
“If we can do something to make our community safer, I believe a ban on micromobility devices coming to and from school is a way to do that,” said Board Member Melissa Byrd.
Board Member Angie Gallo, who is running for chairwoman of the school board, called banning them at elementary school “an absolutely no-brainer” but was more hesitant about prohibiting high school students because she feared it might be government overreach.
“We’re banning something that their parents bought for them,” said Gallo, adding she needed more time to make her decision before she supported restrictions for teenagers.
Angie Gallo
Banning e-scooters and e-bikes for just elementary students but not middle school students could be a “hot mess” in the handful of K-8 schools across the district, added board Member Alicia Farrant who is also running for the board chairwoman role and supported only allowing high schoolers with driver’s licenses to ride them.
Outgoing Gov. Ron DeSantis vetoed a bill last month that some viewed as a first step in addressing the problem. The Legislature does not reconvene until March, so local governments and schools are moving ahead to set their own policies and ordinances without guidance from the state.
Winter Park city commissioners voiced support again at their own meeting this week for adopting their own ordinance before the start of the school year in August, though the proposal hasn’t been finalized yet.
Commissioner Craig Russell, who works at Winter Park High School, said he hopes Winter Park can help set a standard for the state with rules that enforce safety without leaving kids with traffic citations on their records. Winter Garden, in West Orange County, already has an ordinance in place that affects the West Orange Trail that runs through its downtown.
For 90 minutes, OCPS school board members debated what was the appropriate age to allow riding e-bikes and e-scooters. Some questioned who should take the first step to regulate the electric devices — the school district, local governments or the state?
“We can’t control the sidewalks or the roads leading up to the campus,” said Gallo, who supported the district’s push to educate students on road rules. “In my mind, this is a county and a city issue that they need to deal with and provide ordinances that we would follow along with and adhere to. But just us banning them, I don’t think that that makes kids more safe on the roads as they move around Orange County.”
Board Member Stephanie Vanos, who represents Winter Park schools, agreed that the district should lean on local governments to lead on policy decisions. However Vanos viewed the safety situation as too urgent not to act now.
“I’m also honestly just not willing to wait for it,” Vanos said.
In the wake of DeSantis vetoing the bill, Farrant said the district should take the lead.
“We can either point fingers or hope somebody else does it,” Farrant said. “We need to rise up as leaders and do what we can to do our part.”
“We still can only lead so far,” OCPS Board Chair Teresa Jacobs countered as she said she hoped the state would pass a law. “An electric vehicle ought to be regulated similarly to a car.”
The recommendations were discussed at an Orange County School Board work session earlier this week.
Stephanie Vanos
OCPS’ proposed policy would also completely ban modified or Class 3 e-bikes that go faster than 28 miles an hour.
Charging the devices on campus would also not be allowed for safety and fire prevention.
The older students eligible to ride e-bikes and e-scooters would need to register with school administrators.
Superintendent Maria Vazquez warned it would be up to school staff to enforce the rules and oversee the permits.
“I’ve had a few conversations with some principals that see this is going to be a burden because they do not have the staff to follow through and monitor this the way it needs to be,” Vazquez said.
The district will also need to add better signs and more storage and parking for students to park their e-bikes and e-scooters as well as create a safety video.
Alicia Farrant
“From an education standpoint, we are developing a comprehensive informational video for parents and students to improve awareness and micromobility safety, district expectations and responsible use of e-bikes and e-scooters,” said Joe Silvestris, the district’s senior director of the safety and emergency management department.
Some school board members were skeptical the district’s proposed policy could meaningfully solve the problem on campuses.
“Who is regulating it? Who is standing at the door ensuring that the kids riding up have the permit?” Farrant said. “When I’m going out and about, the kids are running through stop signs as if they own the road. … I don’t know that a little video is going to really fix the problem.”
OCPS’ action comes as school districts across the country and state are tackling the issue in different ways, Silvestris said.
Some districts have banned e-bikes and e-scooters completely while others prohibit the class of high-speed electric devices, he said. Schools that allow them require students to dismount on campus entrances and walk them to parking storage areas, he added.
“Schools are experiencing significant increase in student use of e-bikes, e-scooters, and other micromobility devices,” Silvestris said. “This rapid growth has contributed to a rise in injuries and near-miss incidents on and off our school campuses.”
Already the district drafted an incident reporting and data tracking process to better understand the scope of the problem at OCPS and established a working group with principals to share feedback and look at the challenges, Silvestris said.
Orange County and city of Orlando representatives attended Tuesday’s school workshop with Jacobs saying, “Our entire community has a stake in this.”
The attorney and Winter Park resident said he would like to preserve the house. The real estate agent for the sellers said the offer was too low.
July 6, 2026
By Beth Kassab
Matt Morgan, the Morgan & Morgan attorney who lives in a home on Winter Park’s Historic Register, said he made a verbal offer of $10 million last year to purchase the entire Merrywood lot and reinitiated the offer last week with, he said, the intention of preserving the nearly 90-year-old estate that is significant because of its age and as the largest and most ornate home built by architect James Gamble Rogers II.
Mick Night, the real estate agent handling the transaction, said the sellers considered Morgan’s offer to be too low. He said he didn’t include the information in his discussion with the commission because he never had a conversation with Morgan about saving Merrywood.
“There was never a discussion with Matt about preserving the house a year ago,” Night said. “His offer was for the land.”
Morgan agreed that such a discussion did not take place. He added that his offer at the time was not contingent on a lot split and that he is interested in seeing the home maintained.
Lakefront lot splits are generally prohibited by Winter Park, which is why the amendment to the comprehensive plan is required. The change requires a second vote after the state takes 45 to 60 days to review the amendment, likely landing the next time the City Commission considers the matter sometime in August.
A greenlight for the lot split would pave the way for the old house to be demolished — a demolition permit is already active and set to expire Aug. 31 — and two new lakefront homes to be built in its place.
“They [the City Commission] heard there’s no other options … yes there is,” Morgan told the Voice after reading news stories about the vote. “If I see a bulldozer pull up to that house and I didn’t say something, it would bother me.”
Commissioners were told that more than 100 people toured Merrywood and not a single person was willing to purchase and preserve the home because it was too expensive, required too much work or both. Commissioners heard about the attempts to market and sell the estate from one of the sellers as well as the prospective buyer who has the property under a contract that is contingent on the lot split receiving final approval and Night, the Sotheby’s real estate agent who represents them both.
Morgan walked through the home with Night nearly a year ago in early August just as the property became available. Morgan said that a short time later he sent Night a voice memorandum communicating the $10 million offer that he says was not contingent on a lot split. By the time Morgan heard back from Night, he said it was early September and Night told him that that the property went under contract shortly after Morgan toured the estate.
That contract belongs to Tara Tedrow, the land use attorney with the Lowndes law firm who grew up next door to Merrywood and applied for the comprehensive plan change that would allow the lot to be split in two so that she could build a home for her family on one portion while the other is sold.
Night said $10 million was too low for Cathy and Raymond Gilmer, the siblings who inherited the property when their parents, who had lived in the home since 1977, died.
“That was not a number the Gilmers, last summer or anytime since then, have ever been open to selling the property for,” Night said.
Night declined to give the price of Tedrow’s contract on the lot. During a public city work session on June 22 he estimated the land value of the lot to be in the range of $13 million to $15 million.
Night told the City Commission that, while he never listed the home on the MLS, more than 100 people toured the property, including what he estimated to be 15 to 20 people qualified to make such a high-dollar purchase and that none offered to preserve Merrywood.
“All left the property shaking their head, hands in their face,” Night said during a June 22 work session with the City Commission. “They just don’t see it. We haven’t had traction with one buyer.”
Two days later at the regular Commission meeting, Mayor Sheila DeCiccio asked Night: “Is there anyone interested in purchasing that home?”
He replied, “The answer is no. Not one of the viable buyers, much less anyone else, left that house and said, ‘Wow, there’s so much potential here.'”
Night told the Voice on Monday that his comments at the commission meetings intended to convey that he didn’t receive what he considered to be “bona fide offers.”
“There have been many offers,” he said, but none have been “anywhere near reality” on price.
At one point in the June 24 meeting, Tedrow suggested that the price of the Merrywood portion alone would be about $12 million if the lot was split. It’s unclear how that figure is reconciled with Night’s estimate that the land value of the entire lot is at least $13 million.
Morgan said if the city allows the lot split without assurance that the house is preserved then “the city gives everything and gets nothing in return.”
“If the city voted to allow this, they are voting to allow all residents to split lots in the future and get nothing in return,” Morgan said. “It would be one thing if there was some type of meaningful consideration for the city in exchange for the lot split, most notably, preservation of a very important historic home to the city. However, as currently contemplated, in my opinion — the buyers would likely make a meaningful profit and the people (the city) would get nothing in return.”
Morgan isn’t inexperienced when it comes to historic homes. He spent $10.5 million in 2022 for a house that sits on about 3 acres on Winter Park’s Lake Maitland, according to property appraiser records. The 1926 home was designed by Maurice Kressly, another notable local architect, and was placed on the city’s historic register in 2002 by previous owners. It is larger than Merrywood at about 10,000 square feet.
He told the Voice that his original $10 million offer for the entire Merrywood lot still stands and that he made a second $5.5 million offer on Friday to purchase a portion of the lot and preserve Merrywood.
“I think it’s important to the community that the home not be torn down,” Morgan said in a text message to Night on Friday that he shared with the Voice. “For that reason, I am offering to purchase the Merrywood estate for 5.5M. We can split the lot at 1.835 acres each parcel and the current contingency contract holders can build their home on their 1.835 acre lot. I will make a covenant to the city that I will not tear the house down … Alternatively, my offer for 10 million for the entire parcel stands.”
It would be difficult or impossible, according to documents filed with the city and public discussion, to split the lot exactly in half with a straight line from Palmer Avenue to the lake without removing a portion of the Merrywood house that was added on in the 1960s as well as a portion of the swimming pool.
Morgan said if he purchased the entire lot he would also want the ability to split it in the future, but his interest didn’t hinge on that.
“I said of course I’d love that optionality [of a lot split] if I could get it, but it’s such incredible land and such an incredible house that wasn’t a contingency for me,” Morgan said.
He agreed the home is in need of a lot of work and would be expensive to restore. He said if he was the buyer he would look to renovate Merrywood over a number of years and not right away.
The chairman of the board of Friends of Casa Feliz, a group that advocates for preservation and worked with Tedrow and Night to get the word out about the house in hopes of finding a buyer, said news of Morgan’s offer is “extraordinarily encouraging.”
“It demonstrates what many preservation advocates have said from the beginning: Merrywood can be saved, and there is a real market in Winter Park for significant historic properties,” said a statement from Chairman John Bill.
He urged the City Commission to make saving Merrywood a condition of the approval of a lot split.
“To reward the demolition of this resource, now that there is a demonstrated buyer, with a change to our comp plan without requiring designation, would be unconscionable,” the statement said.
At the end of the discussion during the June 24 commission meeting, Tedrow said the sellers were willing to wait until the next vote before they demolish the house even though they are permitted to do so anytime.
DeCiccio said the agreement would “give another 45 to 60 days for someone to come forward for that property and purchase it and designate it historic so we’re buying more time.”
It remains to be seen if Morgan’s offer will be enough, if another buyer will step forward or if Merrywood will be the latest Gamble Rogers house to be reduced to photographs in an archive.
Night and Morgan are planning to meet to discuss the property.
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