by Beth Kassab | Nov 10, 2026 | Arts and Culture, Chain of Lakes, City Commission, Historic Preservation, Zoning and Development
New Plan to Save Most of Historic Merrywood Advances Toward Final Vote
The new terms represent a significant turnabout from just months ago when it appeared the property would be demolished
Nov. 10, 2026
By Beth Kassab
Merrywood may be saved after all — or at least most of it.
An agreement that would preserve at least 80% of the historic lakefront estate’s square footage, along with 70% of the linear footage of its front facade, will be up for approval by the City Commission on Wednesday afternoon.
If approved, the general terms of the amendment to the city’s comprehensive plan would allow the nearly 4-acre lot at 1020 Palmer Avenue to be split in two while adding a deed restriction that runs with the land. The restriction would prohibit the demolition of most of the house and require any additions to be architecturally consistent with “a Mediterranean, Mission, or James Gamble Rogers II influence.”
The deal represents a significant turnabout from just months ago, when the property appeared headed for certain demolition after the previous owners and an earlier prospective buyer said there was no hope of saving it. Last month, the commission delayed the second and final required vote until this month after questions remained about exactly how much of the house would be preserved in exchange for the lot split. The split would be a lucrative benefit for any owner because it would allow a portion of the land to be sold for new construction.
New owner Steve Lockwood, who paid $15 million for the property in August, now appears to be considering Merrywood as a primary residence rather than a “guest house,” as he previously proposed.
Lockwood did not respond to a phone call or text message. Jason Searl, his attorney, also did not respond to a request for comment.
Betsy Owens, executive director of Friends of Casa Feliz, said she was optimistic about the new terms being proposed.
Her group has worked to save the house, which it views as one of the largest and most significant remaining examples of the work of local architect James Gamble Rogers II and a critical piece of the city’s history as told through architecture and design.
“The most significant parts of the house would be preserved, and the front facade is largely being preserved, so it does feel like this is tantamount to preserving the home,” Owens said.
She said some features of the house would be nearly impossible to replicate. She also noted the intrinsic value of owning a piece of Winter Park history that is visible not only from Palmer Avenue but also by boat from Lake Osceola.
A view of the front entrance to the home.
City Planning Director Allison McGillis said the proposed terms would allow the demolition of a sunroom toward the back of the house that was added later, as well as the original maid’s quarters. The other portions would be preserved.
The deal, much like an actual designation on the city’s historic register, would not prohibit the owner from making changes to the interior of the house. The entire layout, for example, could be reimagined, with modern amenities such as a larger kitchen and additional closet space. It’s possible, though, that some aesthetic features, such as tilework or woodwork, could be preserved or reused.
The house, known as Merrywood, is not on the city’s historic register because the longtime owners, who are now deceased, chose not to list it. As a result, it could have been demolished with a simple demolition permit, which became active earlier this year.
However, the property is listed on the Florida Master Site File, a state database of historical and cultural resources. That listing means the city’s Historic Preservation Board could delay a demolition request for 90 days to allow time to consider alternatives or ways to preserve portions of the home.
That process opened the door to public discussions about the house and whether the City Commission should approve the special request to split the 3.67-acre lot without receiving something in return from the property owner — namely, a guarantee that at least some of the home’s historic character would remain standing. Lot splits on lakefront properties are generally prohibited in Winter Park.
The house was featured as one of about a dozen properties in a 2004 book by Patrick and Debra McClane celebrating Gamble Rogers’ architecture in Winter Park.
“The initial series of interior spaces is unusual for a residence and more closely resembles a hotel or theater entry in that a lobby is provided, which is flanked by a coat room and a powder room,” reads the section about the property, which was referred to as the Plant House after its original owner. “Stepping up from the lobby, one then enters a large entrance hall nearly 45 feet in length. Triple arched openings on the south wall of the hall — with a fixed window in the center and double-leaf, multiplane doors on the sides — lead to the loggia and then the sunken patio, with Lake Osceola beyond.”
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by Beth Kassab | Oct 26, 2026 | Arts and Culture, News
Parade of Bands Set to Return to Winter Park This Year
The local football bowl tradition had stopped in recent years because of the College Football Playoff expansion and network-controlled start times. But now officials are trying a new solution
Oct. 26, 2026
By Gabrielle Russon
A beloved Winter Park tradition is returning this holiday season after a two-year absence.
Mark your calendars. The Parade of Bands will march down Park Avenue at 3:30 p.m. Dec. 28, ending with a pep rally in Central Park.
“We are back in the saddle again,” said Johnny Miller, Winter Park’s special events manager. “We’re very excited and very happy to bring back the Parade of Bands.”
The parade was a casualty in 2024 and 2025 because of the College Football Playoff expansion, TV network-controlled start times and an earlier Pop-Tarts Bowl kickoff. That made it tough to bring the two competing university bands to Winter Park before the game. Students ate lunch in Winter Park after the parade and had to reach the stadium on time. Their schedules were packed with other pep rallies, alumni events and other duties.
The logistical issues axed the popular parade, though officials at Florida Citrus Sports said they hoped it would return.
Florida State University drummers took part in a recent Parade of Bands before the event was canceled two years ago. (Photos courtesy of the city of Winter Park.)
This year’s comeback comes with a new solution. For the first time in the parade’s nearly 20-year history, it won’t be held on game day. The parade will be held the day before the Pop-Tarts Bowl kicks off at 5:30 p.m. Dec. 29 at Camping World Stadium.
“We were able to rearrange the schedule and find a spot for it in the afternoon the day before the game to make sure we could host it and bring it back,” said Florida Citrus Sports spokesman Sam Gardner.
That means the bands won’t be as rushed, Miller said.
“The bands can spend a little more time with us and maybe we have a little bit longer of an opportunity to enjoy them,” he said.
Meanwhile, the parade route will remain the same.
Paul Canchester, a retiree from the Chicago suburbs who visits family in Florida every Christmas, called the parade’s return “great news.” Seeing the parade turned into an annual tradition for Canchester who remembered bringing his children to Winter Park since they were young years ago.
“It’s so fun to watch the bands march up Park Avenue and to hear each band play and then to hear them collaborate together at the end,” Canchester said Monday.
The parade comes at a time when many Central Florida governments are scaling back or reconsidering their festive events under an ongoing statewide debate about taxpayer spending and the threat of Amendment 3 which would cut local property tax revenue. For instance, Altamonte Springs canceled next year’s “Red Hot & Boom” July 4 fireworks because of the costs
Dressed in its holiday lights, Winter Park has always been transformed when the two bands march down Park Avenue, making the city, eight miles from Camping World Stadium, feel like the epicenter of Orlando’s bowl game – at least for an hour. Traffic shut down, and people watched the baton twirlers, tuba players and drummers perform down the street. The parade watchers were customers lunching at outdoor restaurant seating on Park Avenue, plenty of families and loyal sports fans cheering on their schools.
The Parade of Bands marches down Park Avenue. (Photos courtesy of the city of Winter Park.)
There were no floats, candy-throwing, politicians or firetrucks. Just music. Throw in the mascots and cheerleaders too.
“It’s all about the band,” Miller said. “It’s nice to be able to highlight and let them have their time to shine other than at halftime of a football game.”
The parade’s weekday date this year also means visitors can ride the SunRail which would ease parking challenges, Miller added.
Winter Park won’t know which two teams are playing until the matchup is set in early December.
Teams with big Central Florida fan bases, like Miami, Florida State or Clemson, could draw even bigger crowds in addition to the locals at the Parade of Bands.
Miller also hopes the parade expands next year to include the two bands in town for the other bowl game, the Citrus Bowl.
“That’s a year away,” he said. “We’ll see what happens with that.”
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by Beth Kassab | Oct 19, 2026 | Arts and Culture, County News, News, Taxes
Jerry Demings Wins Approval for TDT Spending Plan
The amount for the Dr. Phillips arts center was reduced and commissioners rejected a bid to give the convention center more money
Oct. 19, 2026
By Beth Kassab
The Orange County Commission on Monday approved nearly $1 billion in projects funded by tourist development tax revenue, including new sports facilities at UCF and a $50 million reduction in funding for the Dr. Phillips Center for the Performing Arts.
A last-minute push to include several hundred million dollars for another expansion of the Orange County Convention Center, which has already cost $2 billion, failed to gain support from any commissioner except Mike Crabb, who was appointed to Seat 2 in August by Gov. Ron DeSantis.
Representatives of the tourism industry joined forces with local labor union members in an unusual alliance to urge Mayor Jerry Demings to delay a vote on his plan to spend $860 million on 13 projects. Demings refused, arguing that a delay could mean many projects he considered worthy might never get another chance at funding. He also bristled at assertions that the decision-making process lacked transparency or had been rushed, rejecting the suggestion that he should leave the matter to whoever is elected mayor next month.
“Yes, [the end of] our tenure is for some of us just months away, but it doesn’t mean that we should just sit here and do nothing,” Demings said. “This is my home, where I was born and raised. For nearly seven decades, I’ve lived here. I have put my life on the line for this community. Been in some tough situations over the years. My blood, my sweat, my tears have gone into working on behalf of this community. I will not retreat from working in my home and taking care of the people who live here.”
The 6-1 vote followed five hours of public testimony and debate.
Commissioner Kelly Semrad, who represents Winter Park, voted against the plan. Demings, Nicole Wilson, Crabb, Mayra Uribe, Maribel Gomez Cordero and Mike Scott voted in favor. Demings and Uribe are set to leave office soon, while Crabb and Scott are seeking election on Nov. 3.
Kelly Semrad
Nine speakers, many of whom worked in hotel management or other senior hospitality positions, urged the commission to add the convention center expansion to Demings’ list of projects.
Demings, however, said he was unwilling to consider such a change. The previous expansion, for which he helped secure funding, is still under construction, and he questioned whether another expansion was necessary for the center to remain nationally competitive.
“How big is big enough?” Demings asked. “How big is too big? And there are citizens who think that that’s not the appropriate place to make investments.”
Crabb twice attempted to amend Demings’ plan. He presented a spreadsheet he had prepared with different funding amounts for the projects to make room for the convention center expansion. After his first motion failed, he tried again, this time seeking to delay votes on both the convention center and the arts center while funding the other projects. Both times the other commissioners sat in silence rather than offering a second for his motions and both failed.
At least 14 of the 78 speakers told commissioners they were concerned about transportation in Orange County and wanted some tourist tax revenue directed toward improving roads, bus service and rail.
“I point out all these venues that you want to additionally fund are functional. They have options,” said Eugene Staccardo, a resident and civic activist. “This community doesn’t have an adequate transit system for tourism, even after billions of dollars of upgrades to I-4. It’s functionally not meeting the needs of [the] community … Say no to these large TDT proposals that will financially tie our hands for decades. Reserve the money for the future and to be used on hopefully a future transit system.”
Demings said he did not believe the Florida Legislature would expand the legally permitted uses of tourist development tax revenue to allow Orange County to spend the money on local needs such as public transportation.
“This legislature and those in the immediate past have not been so kind to this community,” he said. “They preempted us left and right. We have been left to figure it out on our own … Every one of these projects that we talked about today will add jobs. You would think that not any of those jobs are good jobs, but I’m here to tell you, many of those jobs are good jobs.”
Florida lawmakers have, however, granted exceptions allowing specific communities to use tourist tax revenue for local needs, such as affordable housing and public safety, after those communities mounted strong campaigns for the changes.
Semrad questioned why her colleagues were willing to disregard both residents’ concerns about transportation and projections in Demings’ own plan showing that TDT reserves would fall below the recommended $300 million threshold in the coming years as a result of the spending.
Demings and county staff members said the projections assumed annual TDT revenue growth of 2% over much of the next 10 years, though actual growth could be higher. They also said the county’s convention center capital spending plan includes additional TDT revenue for projects such as elevator repairs and fire alarm system replacements. Because those funds are not always fully spent, they argued, the projections were conservative.
“You’re okay with it, and I hear all the reasons why that math works,” Semrad told the group. “But I’m also familiar with market uncertainty and the conditions in today’s marketplace that are concerning, and that numbers could soften, especially in terms of travel. We all see it at the pumps. You guys, anybody who’s bought an airline ticket lately knows how expensive it’s getting. It’s going to impact our tourism industry … So I’m uncomfortable when I see red numbers.”
Ultimately, Uribe moved to keep reserves at the recommended threshold by reducing the allocation for the Dr. Phillips Center for the Performing Arts from $400 million to $350 million.
The arts center is receiving the largest share of the mayor’s TDT spending plan to build new theaters, add parking and make other improvements.
Kathy Ramsberger, the center’s president and CEO, addressed the commission and confirmed that the center could still move forward with its projects under the reduced allocation.
The following slides show the approved spending plan with the exception of the reduced arts center figure:
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by Beth Kassab | Oct 19, 2026 | Arts and Culture, County News, News, Taxes
What's Going On? I-Drive Chamber, Unions, Kelly Semrad All Call to Slow Down Giving Away TDT Money
The unusual allies expressed concerns ahead of a meeting today where the County Commission is set to consider Mayor Jerry Demings’ plan to give out nearly $1 billion
Oct. 19, 2026
By Beth Kassab
When the Chamber of Commerce that represents the largest tourism interests on International Drive aligns with both the local labor union and the county commissioner who was elected on a campaign of pushing back against tourism’s political power, it’s a rare day in Orange County.
Those unusual allies appear to have different motivations, but they’re calling for the same thing: They want Orange Mayor Jerry Demings to slow down his push to allocate nearly $1 billion in Tourist Development Tax revenue to 13 projects without subjecting each one to greater scrutiny or more fully assessing what local communities will need over the long term.
Today, those groups will be seeking answers to a number of questions when Demings and County Commissioners meet this afternoon for a special meeting at which Demings will seek approval of his recommendations for the 13 projects.
Among those questions, which center on a process that began in late July with the first meeting of Demings’ 34-member citizen task force to evaluate the projects, are:
- How and why was a proposal to spend $46 million on new soccer and track-and-field facilities at the University of Central Florida (UCF) added back to Demings’ list as his 13th recommendation after the citizen task force made only 12 recommendations and funding for UCF didn’t even garner enough support for a full vote?
- Will proponents of another expansion of the Orange County Convention Center succeed in getting that project added to the recommendation list in the final hours, even though the citizen task force also rejected it?
- Were all the projects evaluated using the same comparable metrics and standards agreed upon by the task force to justify the use of public dollars?
- If the County Commission funds all 13 projects at the recommended levels, will any additional hotel bed-tax revenue be available for transportation or other local needs if the state eventually allows the expanded uses of the tax revenue recommended by the citizen task force? Both candidates seeking to become Florida’s next governor have expressed support for expanding those uses.
“Government moves slow until you put a billion dollars on the table for the tourism industry then it moves at the speed of light,” said Commissioner Kelly Semrad, who represents Winter Park, describing the timeline, which began less than three months ago.
Today’s meeting could provide the last major opportunity for debate on Demings’ plan to spend more than $860 million, mostly over the next 10 years. Some of the financial obligations, however, would extend much longer. Debt service on a major expansion of the Dr. Phillips Center for the Performing Arts, for example, would cost about $32.8 million annually for as long as 30 years.
The plan outlined by Mayor Jerry Demings as presented recently to county commissioners.
The meeting comes just two weeks before Election Day, when voters will select a new mayor and four commissioners, and about eight weeks before the winners are sworn into office.
John Stine, chairman of the International Drive Resort Area Chamber of Commerce, called the process “rushed and flawed” in a letter to the editor published in Sunday’s Orlando Sentinel.
“County commissioners have a responsibility to independently examine the recommendations before committing funds,” Stine wrote. “A task force recommendation should begin that scrutiny, not replace it. Unanswered questions require answers. Incomplete financial information requires further review.”
Similarly, the union representing food-service, housekeeping, and other workers at Walt Disney World and hotels near Universal Orlando and the Convention Center called for more time before the financial commitments are finalized.
Union leaders said Sunday in a news release that they would hold a news conference just before Demings’ meeting to urge the county to “take more time to evaluate the size and scope of the proposed commitments, provide greater transparency on the TDT financial picture, preserve flexibility for future transportation investments, and ensure tourism workers and the incoming County Commission have an opportunity to weigh in before long-term decisions are finalized.”
According to the county webpage dedicated to the citizen task force, today’s work session will be followed by a special Tourist Development Tax meeting on Nov. 6 and then a regular County Commission meeting on Dec. 1, just days before Demings is scheduled to leave office.
Linda Chapin, the former Orange County mayor who served as co-chair of the citizen task force, defended its process in an interview with the Voice on Sunday.
“We spent twice as much time on this task force as the last one did,” Chapin said. “We heard from three times as many applicants as the last one did, and we worked very hard to make sure this money benefited people across the community, so I will be very disappointed if they don’t move ahead.”
She said she was pleased that projects from Ocoee to Eatonville to more money to be handed out later to smaller arts organizations made it into the recommendations. She pointed to recent projects in Winter Park that received tourist development tax dollars such as the Rollins art museum and the Winter Park Playhouse as examples of how the tax is benefiting communities across the county rather than just in the central tourism areas.
Chapin did acknowledge, however, that she was “a little surprised” to see UCF’s project added to Demings’ recommendations after no one on the task force seconded a motion to include it among the projects the group endorsed.
She also said she was “very frustrated” that the task force was never given specifics about how much money it had to work with as it met in July and August.
A PowerPoint presentation provided to commissioners by county staff last week included a chart showing that the projected costs of the 13 projects would exceed revenues from 2028 through 2032 before the balance returned to positive territory in 2033. The tax’s unallocated cash reserves, or rainy-day fund, would dip below the comptroller’s recommended target of $300 million in 2031, 2032, and 2033, according to projections that assume 8% growth in TDT revenue in 2026 and 2% annual growth thereafter.
But Chapin dismissed the notion that funding the recommended projects would tie up all available funds for the next decade. She also said she was concerned about what might really be driving some calls to slow the process until a new County Commission takes office.
“I fear that for some of these people, not all, it’s a ploy to see if they can put it off until the next board so they can give money to the convention center,” Chapin said.
She plans to attend today’s work session and said, “if I need to issue a red flag about the convention center, I’ll stand up and do it.”
Semrad and others, including Winter Park Mayor Sheila DeCiccio, who advocate directing more of the tax revenue toward local needs such as transportation infrastructure, say the latest convention center expansion’s failure to win approval from the task force was a victory for the community. They view the convention center, which has already cost $2 billion, as primarily benefiting hotels and businesses along International Drive.
Mike Crabb, who was appointed by Gov. Ron DeSantis to represent District 2, which includes Apopka, and is now in a runoff on Nov. 3 against Kamia Brown, sent a memo to fellow commissioners last week urging them to add the convention center back to the list of projects slated for funding. Among other recommendations, he suggested allocating $523 million to the convention center while reducing the $400 million Demings recommended for the Dr. Phillips Center for the Performing Arts to $150 million.
Commissioner Mike Scott, who represents the International Drive area, along with Tangelo Park and Pine Hills, and is seeking reelection next month against Lawanna Gelzer, also pushed to reconsider the convention center at a recent commission meeting.
Roseann Harrington, Demings’ chief of staff, said in an email to Semrad that the mayor had the discretion to add UCF back to the list because “commissioners mentioned three times” when they accepted the task force’s recommendations in August that the action “did not limit them to only selecting among the 12 recommended by the TDT Task Force. Commissioners expressed interest in the Orange County Convention Center (OCCC) and UCF.”
When Semrad, a UCF professor who studies hospitality economics, asked for more detail about how the projects were evaluated for economic impact and why the county used a traditional economic analysis rather than what she considered more informative measures — such as jobs and wages, geographic reach, long-term operating costs, financial sustainability, and future TDT revenue generation — Harrington suggested that Semrad conduct her own analysis.
“After speaking with six of the seven BCC members on the type of fiscal analysis they would like conducted, the consensus was to do a traditional economic analysis consistent with the work done by GSU,” Harrington wrote. “With that said, since you have expertise in financial and community analysis, please feel free to do your own research and we will be glad to distribute to the BCC.”
Semrad argued that clearer guidelines were needed not only for the metrics but also for the process.
“My concern is that both the applicant pool and the scope of that analysis appear to have changed without further public Board discussion,” she wrote to Harrington.
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by Beth Kassab | Oct 13, 2026 | Arts and Culture, Events, News
Photo Gallery: First Pumpkin Patch near City Hall
The pumpkin patch runs through Oct. 25 and benefits the Park Avenue District
Oct. 13, 2026
By Gabrielle Russon
About 2,200 people have visited the first-ever pumpkin patch that’s sprouted up by Winter Park City Hall.
Volunteers from schools and local businesses have picked up 150 shifts to help run the patch that will stay open through Oct. 25. The proceeds will benefit the Park Avenue District which supports small businesses and promotes the shopping and restaurant hub, said Allison Chandler, the district’s executive director.
“The new activation is part of the Park Avenue District’s growing investment in experiences that bring the community together, support local businesses and create new traditions while preserving the character and charm of Park Avenue,” the organization said in a news release.
The hours are 3 p.m. to 7 p.m., Monday–Thursday and from 9 a.m. to 6 p.m. on Friday, Saturday and Sunday.
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by Beth Kassab | Sep 15, 2026 | Arts and Culture, City Commission, News, Taxes
Parking Fines to Increase, E-Bike Fines also added as Budget is Finalized
The City Commission also reduced the amount of money set to go to nonprofit Men of Integrity Mentoring Program and turned down requests to add dollars for the library and Blue Bamboo back into the budget
Sept. 15, 2026
By Beth Kassab
Winter Park will bring in additional revenue next year through higher fines for parking tickets, fees for non-residents to park at Dinky Dock and the dog park at Lake Baldwin, and new fines for kids and adults who violate recently approved rules governing the use of e-bikes and e-scooters.
The City Commission also made last-minute tweaks to the budget that takes effect Oct. 1, reducing the amount of money the nonprofit Men of Integrity Mentoring Program will receive and rejecting calls to restore cuts to the Winter Park Library and Blue Bamboo.
Some details remain unclear, including exactly how much the new fines for parking and micromobility violations could bring in.
The fees for non-residents to park at Dinky Dock and the dog park have not yet been set but could be in the range of $2 to $3 per hour. The pilot program is expected to start later in the year after a company is selected to administer it.
Motorists who park along the curb facing the wrong direction, overstay the allotted time at a curb or otherwise park in an unlawful manner will now face a $30 fine, up from $25.
Commissioner Elizabeth Ingram pushed for even higher parking fines, noting that the discussion occurred during a meeting that lasted more than five hours, with a substantial portion devoted to parking concerns related to a proposal to build a synagogue and daycare downtown.
She said she was “shocked” to learn that parking fines are only $25 and suggested they could be as high as $75 or even $150 to help change motorists’ behavior.
“It doesn’t hurt enough to teach someone,” she said.
City Manager Randy Knight warned that complaints would pour in if fines were raised that high.
“We get complaints about $25 all the time, and so if you go to $75 … maybe you each get to serve as cashier one day a week,” he said in jest.
Police Chief Tim Volkerson said his team issues parking fines every day and noted that Orlando recently raised its fine to $35.
The commission settled on a $30 fine for parking violations.
The group also raised the fines for violating the new micromobility ordinance to $35 for a first offense and $75 for a second offense.
When it came to the portion of the budget — about $480,000 — that the city spends on local nonprofit groups, a proposed $45,000 allocation for Men of Integrity was reduced to $20,000.
Commissioner Warren Lindsey said he wasn’t comfortable with the amount, given that the group is already provided free space at the Community Center and because commissioners are being forced to make some cuts that he called “painful and uncomfortable.”
Men of Integrity serves about 24 boys, including 10 in high school and 14 under the age of 12, said Antwon Carter, the group’s leader. Many of the kids attend Winter Park schools, but some travel from outside the city to attend the weekly program. An administrator for the program provided the Voice with a copy of Men of Integrity’s most recent tax form, which shows that the group’s revenues are typically less than $50,000.
Ingram attempted to restore some funding for Blue Bamboo in response to pleas from one of the group’s leaders but did not win enough support.
Officials from the Winter Park Library also asked the commission to consider restoring a $25,000 cut to its budget but did not win support.
Even with the $25,000 reduction, the Winter Park Library is still slated to receive nearly $50,000 more than last year in support from the city’s main budget and the Community Redevelopment Agency budget, for a total of $2.5 million.
The second required vote on the city budget is scheduled for Sept. 23.
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