On the Chopping Block: Police, Fire, Community Groups, Trash Collection
This week, in an email to residents, Mayor Sheila DeCiccio asked what should be cut in the city budget as a result of state-ordered reductions
Aug. 7, 2026
By Beth Kassab
After years of stripping power from locally elected mayors and commissions when it comes to everything from regulating where apartments can be built and how tall to whether cities can ban gas-powered leaf blowers or plastic straws, state leaders have reached a new level of micro-managing local governments: mandatory lists of budget fat.
Cities and counties will be required to publish those lists starting next year as a result of a new law (HB1329) signed by Gov. Ron DeSantis this summer.
But Winter Park is getting a jump on the exercise.
With potential property tax cuts looming in the form of Amendment 3 on the November ballot, city managers asked each department to lay out cuts to reduce their budgets by 10% (This exercise will be mandatory for local governments next year as a result of the new law.)
The results?
Here’s just a sample of what’s on the budget fat list in City Hall:
Eliminate a code enforcement officer position that is currently vacant ($75,000)
Eliminate funding for the Public Art Advisory Board ($15,000)
Eliminate the mailed printed version of quarterly Winter Park Update newsletter and monthly inserts in utility bills ($71,900)
Eliminate the use of accepting cash for city services like permits or other needs at the City Hall windows ($50,000)
Eliminate two vacant firefighter positions ($200,000)
Close a Fire Rescue engine company ($1.25 million)
Begin closing the library every Monday ($210,000)
Reduce garbage collection to one day per week ($300,000)
Reduce tree plantings, canopy maintenance and eliminate residential tree permits among other changes ($600,000 combined)
Eliminate the Historic Preservation Grant Program ($100,000)
Eliminate four police detectives, one traffic officer, one community service officer and two officers dedicated to homeless outreach ($1.15 million)
Eliminate body-worn cameras and live crime center for the police department ($300,000)
Reduce funding to community organizations such as the Winter Park History Museum, the Albin Polasek Museum & Sculpture Gardens, Mead Botanical Garden, Blue Bamboo and more. ($243,500)
You get the idea. And that’s not the complete list.
Also, to be clear, the spreadsheet of potential cuts provided by City Hall included about 45 items. Some of those were ways to increase revenue for the city (such as adding more red light cameras, which could result in $750,000 in new revenue). Even so, the total did not add up to $9.5 million or about 10% of the proposed budget’s nearly $95 million general fund. The proposed all-funds budget, which includes the utilities and other funds, is up to $247 million.
The Voice totaled the spreadsheet to about a $7.8 million overall reduction (including some revenue gains proposed).
“As you can see, getting to a budget cut of 10% would not be painless,” Mayor Sheila DeCiccio told the community in an email she sent out this week. “It could mean fewer police officers and detectives, longer emergency response times, reduced park maintenance, one-day a week trash collection, and fewer community programs.”
She asked residents in the email what they prefer to cut, explaining, “I’m writing this email because I believe you, our Winter Park residents, deserve to see the potential cuts that are being discussed. As always, I’m committed to full transparency.”
Winter Park staff estimates Amendment 3 would require cuts of $3.4 million in 2028 and $6.7 million in 2029. So far shy of the 10% exercise. But not far off once a few years into the new tax structure if it wins by the required 60% of voters in November.
The Voice has heard from some readers who appear to be under the impression that police and fire or other “essential services” can not be cut under Amendment 3, which would increase the homestead exemption ultimately to $250,000.
But that’s not the case. Cities and counties will still provide emergency services, to be sure, but at what level?
Florida House Republicans approved language that would ban local governments from reducing money for law enforcement, firefighters, and first responders below the level in either fiscal year 2025-26 or 2026-27, whichever was higher. But the Senate never approved that version and it died during the Legislative session.
That’s why police and sheriffs’ organizations have spoken out about the potential impact of the amendment and cuts that could result from it.
“The Florida Sheriffs Association is significantly concerned with Constitutional Amendment 3, which potentially allows Tallahassee to control your local budgets, creates longer law enforcement response times, limits communities’ abilities to provide road repairs and stormwater removal — these are a few things voters deserve to be aware of,” the organization said this week on Facebook.
And the soaring cost of police and fire service is a main driver of the growth in the budget the City Commission will consider this month.
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.
In 2021, for example, the starting salary for a Winter Park police officer was $22.84 an hour or about $48,000 a year. Today it’s $30.34 an hour or more than $63,000 a year.
Police Chief Tim Volkerson has said the increases are the result of pressure on wages from other departments who have raised pay as they have struggled to hire and retain officer.
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.
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.)
The City Commission is slated to hear public input and consider portion of the budget at this meetings this month on Aug. 12 and Aug. 26 before final adoption of the budget by the end of September.
Synagogue, Daycare and Townhomes Win Approval from Planning Board
A number of residents spoke for and against the project that will result in the first permanent synagogue in Winter Park
Aug. 5, 2026
By Beth Kassab
After more than 20 residents spoke out during a two-and-a-half hour discussion, Winter Park’s first permanent synagogue won unanimous approval on Tuesday evening from the Planning & Zoning Board.
While some who addressed the board expressed concerns about traffic related to a daycare that will be run by Chabad of Greater Orlando and also noise or other neighborhood disruptions from a rooftop patio proposed for the top of the building, the board members said most of their questions about the development were answered.
The P& Z board added one condition to its approval the development, which also includes five townhomes at the 0.6-acre site at the corner of Morse Boulevard and Knowles Avenue where the El Cortez apartment buildings stand today.
Board members voted 5-0 to adopt the conditions recommended by staff and add a requirement that child drop-off and pick-up related to the daycare take place in the underground parking area planned for the synagogue.(Chairman Jason Johnson and members Bill Segal, Vashon Sarkisian, Samuel King and Charles Steinberg were in favor. Member Alex Stringfellow, who works as an urban planner and was asked to consult on the project before the application was made, recused himself from the vote and member Michael Dick was absent) The other conditions include prohibiting speakers or amplified music on the rooftop patio; requiring all noise and lights from the rooftop end by 10 p.m.; any expansion of the synagogue or daycare must go back to the city for approval and car lines related to daycare drop-off or pick-up can not spill onto the public streets.
A more modern design for the new Chabad of Greater Orlando was favored by the Planning & Zoning Board.
“It’s clear that this property could be developed at a higher capacity, which is going to bring up a whole lot of issues regarding parking and traffic,” said member Vashon Sarkisian, an urban designer. “So I think we have to consider that this is, you know, a coveted area and that there’s going to be redevelopment … so what is the right use? Well, I am in favor of this use. I think it’s, like so many people said, it’s something that’s missing in the city of Winter Park.”
Earlier in the evening, Jewish residents spoke about their desire to have a synagogue closer to their homes and the positive impact of Chabad on their lives.
“Chabad has been a part of my life for a long time. It’s where my parents met. It’s where I celebrated my Bar Mitzvah, and it’s where I’ve celebrated all my holidays,” said Daniel Isaak, 16. “… It’s about allowing a community to worship where it already lives. You know, all of my Christian friends, they all have churches in their own city, and they can practice their faith close to home surrounded by their neighbors. So why should Jewish families have to leave their own community to do the same?”
The 40-year-old organization lost its Maitland building to a fire in 2024 and has been operating out of a temporary space on the far end of North Park Avenue.
Several people who attend Chabad said only 12 to 15 people typically are at Friday evening services.
The proposal, which still must be approved by the City Commission, is capped at 80 seats in the synagogue and the daycare is limited to 60 children. The five townhomes on the site are being developed separately and will be sold once completed.
Rabbi Dovid Dubov said many people who will attend services or use the daycare will walk rather than drive, which will help alleviate traffic concerns. Jewish law prohibits driving on Shabbat, for example.
“Our responsibility is to make Jewish education available where Jewish families live,” Dubov told the board. “And today, ladies and gentlemen, there is no Jewish daycare in Winter Park. We have also worked diligently to be respectful of our neighbors. We voluntarily limited our daycare to just 60 children, approximately one-fifth the size of nearby church schools, and our traffic study demonstrates that that impact will be extremely minimal.”
But some residents who live in nearby townhomes and condominiums questioned the accuracy of the traffic study and noted how congested the small roads already become as a result of the Methodist Church preschool across Morse Boulevard and other church schools just blocks away.
Frank Santos, who lives next door, said the area is already undergoing enormous change and contending with traffic and parking problems. Santos, chief executive officer of Rosen Hotels & Resorts, which has a long history of supporting local Jewish causes led by its late founder Harris Rosen, said his own rooftop living space will be impacted by as many as 80 people using the synagogue’s rooftop deck because of the proximity.
“Chabad of Greater Orlando and it’s member should have a synagogue in Winter Park,” Santos said. “Knowles Avenue is not the right location. Find a site with less density and appropriate parking.”
Marc Hagle, who is known for constructing the largest private residence in Winter Park at 40,000-square-feet on Palmer Avenue and for taking two Blue Origin suborbital space flights in recent years, said he attended the meeting with the intention of speaking against the project, but was impressed by the presentation. Still, he noted potential traffic congestion and also questioned if redeveloping the site mostly as a synagogue would have a negative tax impact to the city because religious institutions are generally exempt from paying property taxes.
“I think the tax implications to the city are a problem,” Hagle said. “The city is facing some really interesting tax problems coming up with the laws that are changing,” he noted, an apparent reference to the amendment on the November ballot that could significantly decrease property taxes collected by local governments.
The El Cortez Apartments along Morse Boulevard.
“By putting something in the area that’s tax exempt, I think you’re creating a potential problem for the future,” he said. “We’re all interested in making sure that the city meets its obligations and it maintains standards that, quite frankly, the city hasn’t done for the past five to ten years. This isn’t the right place to say this, but the quality in the city isn’t what it used to be.”
Several longtime Winter Park residents who are Jewish noted the meaning of the synagogue after a history of discrimination against Jews across the country, including in Winter Park.
“It has been a problem being Jewish in Winter Park, to be candid,” said Barry Render, a former longtime Rollins College professor. “When I moved into my house on Via Tuscany and applied for membership in the Racket Club, which is just a block away from me, I was turned down because I was Jewish.”
He also noted that the holiday celebration in Central Park did not always include a Hanukkah menorah as it does today.
David Jasmund, who lives close to the site on Interlachen Avenue, was one of several people who attended the meeting who said they were “disappointed” that any of the concerns about the development were being linked to bigotry.
“That’s disappointing,” he said. “Unfortunately, it’s around us today in society, which I think is really depressing at times.”
Jasmund said he didn’t have any concerns related to the synagogue itself, but questioned the capacity of the roads to handle another daycare in such close proximity to others.
“I think it’s unrealistic to think that someone is going to drive a 1-year-old or a 2-year-old down into a basement … take them out of a car seat, take them upstairs, and get 60 people in and out of there without it being stacked up on Morse, Interlochen, Knowles, and maybe even Park Avenue.”
Hattie Wolfe, another speaker who lives nearby, said parking in the area is already “impossible.”
A rendering shows what the townhomes on the site will look like.
“I’m Jewish,” she said. “I have nothing against the synagogue, but I don’t think it’s the right place for it, judging by what’s happening to the town.”
Becky Wilson, the Lowndes law firm attorney who is representing the synagogue and often represents development projects in Winter Park, said the project is doing everything possible to address concerns about traffic, parking and density.
“I think what occurred to me and that I’ve grown to appreciate while working on this project is how important having a synagogue in the city of Winter Park is to the Jewish residents,” she said. “And, in particular, to have one downtown where many of the other large, important churches are also located. What I’d also say to those residents is I’ve stood here for over 20 years, and I’ve never brought a project forward where I didn’t have to answer questions about traffic, parking and density.”
P&Z Chairman Jason Johnson asked Wilson if Chabad would agree to the condition that daycare pick-up and drop-off must occur in the underground garage to help with traffic flow and she said the group would agree. He suggested parking on the site is likely a “net benefit” for the downtown area once El Cortez is gone because people utilize street parking related to the apartments.
“There are people I deeply respect on both sides of the issue who have made their their comments to the board tonight,” Johnson said. “… My main concern with the traffic was not the number of trips, but rather the flow of traffic through the site for day care drop-off and pick-up. I think if that traffic flow can be directed directly into the garage below the facility, it would help alleviate that quite a bit.”
The next step for the project is a hearing in front of the City Commission.
So Far, No Response to Matt Morgan's Offer for Merrywood
The attorney and Winter Park resident now says he is willing to pay $12 million for the property in hopes of preserving the historic home
July 27, 2026
By Beth Kassab
Matt Morgan, who increased his offer this month from $10 million to $12 million for Merrywood, says he has not received any response from the sellers.
That means the future of the nearly 90-year-old estate designed by James Gamble Rogers II remains in limbo as an August vote nears for the City Commission to decide if the current buyer with a contract on the property will be allowed to split the large lot on Lake Osceola in two. Winter Park’s land development rules generally prohibit subdividing lakefront lots so Tara Tedrow, the buyer with the contract, is seeking special permission.
Morgan told the Voice he has not heard back since putting his offer in writing more than two weeks ago.
Mick Night, the Sotheby’s real estate agent handling the transaction on behalf of the longtime owners and for Tedrow, did not respond to requests for comment. Tedrow also did not respond to messages seeking comment on Morgan’s offer.
A demolition permit remains posted at 1020 Palmer Ave., though city officials say a list of tasks that must be done before the bulldozers roll in have not yet been completed such as certifying the water and power is shut off, an inspection for pests and draining the air-conditioning system.
A demolition permit is posted outside 1020 Palmer Ave. (Photo by Gabrielle Russon)
Morgan, a Winter Park resident known as a key face of the Morgan & Morgan law firm, first 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.
The Voice first reported his offer earlier this month after Morgan came forward in response to news reports that the house was all but guaranteed to be torn down after Night told the City Commission that no one wanted to pay to maintain it despite nearly a year of searching by himself, Tedrow and local preservationists for a way to keep Merrywood. The City Commission voted 3-2 on June 24 in the first of two required votes to approve the lot split.
Shortly after that meeting, Morgan said his original offer still stood and then increased what he said he is willing to pay to $12 million, a price he said he based on his understanding of the amount Tedrow agreed to pay under her contract that is contingent on the city approving the lot split.
“In my view, my offer solves all of the current problems,” Morgan told Mayor Sheila DeCiccio and commissioners in an email on July 10. “Tara Tedrow has expressed her desire to have the historic home preserved and also build a personal residence on the other lot, which is very close to her childhood home. At the time of the hearing, my desire to preserve Merrywood was not known. After hearing there was a strong desire to preserve the home by the contract holders, I immediately came forward to offer this solution. My current offer is pending and I have not heard back yet, but I am very optimistic. My offer allows [current owners Ray and Cathy Gilmer] to receive their current contract price either which way.”
He said he would be willing to purchase the entire lot or a portion of the lot, if the split is allowed, that is needed to keep the home in place.
“I am offering to purchase the estate portion at the same pro rata value established by their own contract while preserving one of Winter Park’s most significant historic homes,” Morgan wrote. “The city no longer has to choose between fairness to the owners and preservation of Merrywood. It can accomplish both without changing its Comprehensive Plan for a single property.”
Morgan’s email to city officials was in response to an email from Night to the mayor and commission with the subject line “Merrywood Rumors.” Morgan said Night is a “man of integrity” in response to Night’s defense of his assertions to the City Commission that there were no alternatives to demolishing Merrywood.
“First of all, I stand by any representations at the recent June 24 hearing about the lack of interested buyers or offers to preserve Merrywood, regardless of errant rumors being circulated surrounding the Matt Morgan offer made last August 2025,” Night wrote.
He went on to explain that he did not discuss preserving the home with Morgan at the time of the original offer last year and that the sellers did not consider $10 million “within the range of what they were willing to sell the property for, then or now.”
Those points were reported in the Voice story about Morgan’s offer on July 6, four days before Night’s email to city officials.
“Matt and I have spoken several times in good faith this week, with a mutual interest in continuing to do anything either of us could to save Merrywood, in addition to the collective and well-publicized ongoing efforts for almost a year now,” Night wrote on the afternoon of July 10.
In Winter Park, the local historic register offers protections against buildings being demolished. But joining the register is voluntary and must be done by the owners. In the case of Merrywood, the longtime owners deliberately kept the property off the register in the event it would be worth more as a tear down.
The city’s historic preservation rules do not govern or prohibit interior renovations and apply to the look and materials on the exterior.
Vacant land on Winter Park’s picturesque chain of lakes is scarce.
But how much the property is worth has been the subject of varying views during the discussions over whether the home should be saved.
Night said at a public meeting that the entire lot is estimated between $13 million and $15 million. He said during a June 22 work session with the city commission that it would be just the seventh transaction higher than $10 million in Winter Park.
Commissioner Elizabeth Ingram asked Tedrow during the June 24 meeting what a “realistic amount” would be for the portion of the lot that included Merrywood if the lot was divided into two pieces.
“Real estate prices are going to be determined on a per acre basis,” Tedrow said. “And if you look at market comps, again I don’t set market comps those are set by recent sales data … I mean, you’re looking at just for the Merrywood site, you are over $12 [million].”
It’s unclear how Tedrow’s figure for just a portion of the lot of more than $12 million reconciles with Night’s estimate of $13 million to $15 million for the entire lot and the reported price of $12 million for the contract held by Tedrow for the entire lot contingent on approval of a split.
City officials allowed one other lakefront lot split in recent years that also involved a Gamble Rogers home, but with two key distinctions from Tedrow’s request. In 2024, the commission changed the Comprehensive Plan in a way to allow for a lot split at 1290 N. Park Avenue, but in that instance the newly created lot was not on the lakefront and the owners were required to designate the existing 1930 home on Lake Maitland as historic on the city’s register.
City staff recommended approval of Tedrow’s request also come with a condition that Merrywood be designated historic, but both the Planning and Zoning Board and City Commission rejected that condition after they were told by the owners, Tedrow and Night that the home is in disrepair and no one was willing to purchase it and restore it. Morgan made his offer public after those votes.
The number of Gamble Rogers houses in Winter Park is shrinking each year as they are torn down for new construction. Fewer than 25 quality examples are estimated to remain.
Gamble Rogers is also known for designing the Florida Supreme Court, Olin Library at Rollins College and Greenada Court on Park Avenue, a Mediterranean-style courtyard with a fountain and tables often occupied by shoppers sipping Barnie’s Coffee. Casa Feliz, one of his most well-known works because it’s now a popular event venue and museum, was nearly torn down 25 years ago until the community rallied to raise money and move it to its current post just off the Winter Park Nine.
His body of work resulted in Gamble Rogers being credited with influencing the aesthetic and feel of Winter Park, which the New York Times has described as “more like a village than a suburb” because of its elevated planning, design and walkability and as a “sophisticated alternative to Disney.”
“As with [Frank Lloyd] Wright’s work in Oak Park, Illinois, and [Addison] Mizner’s work in Palm Beach, Rogers’ work in Winter Park created an architectural character for the town,” wrote Patrick W. McClane and Debra A McClane in “The Architecture of James Gamble Rogers II,” which featured a section on Merrywood. “It can be argued that the publication of many of his designs also exerted at least some influence on a national level by exposing Florida architecture to a national audience.”
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.
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.
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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