What Does Winter Park Stand to Lose if Property Tax Cuts Pass?
Voters are expected to decide a ballot amendment in November initiated by Gov. Ron DeSantis and the Florida Legislature that could dramatically alter how local governments operate
June 5, 2026
By Beth Kassab
What does Winter Park stand to lose if voters approve the plan by Gov. Ron DeSantis and the Legislature to dramatically reduce property taxes?
A picture of the potential fallout is becoming more clear just days after the Florida House and Senate voted to send the measure to the November ballot. Here’s what we know so far:
How much money will Winter Park lose?
Let’s break down the numbers.
In 2025, Winter Park collected about $48.5 million in taxes, according to Orange County Tax Collector Scott Randolph. The bulk of that, or about $41.1 million, is what is targeted by the state ballot amendment. Those are the dollars collected on real property — houses and businesses — based on that property’s assessed value.
Tax money that comes in from real property is divided into two categories: Homestead (the houses people live in and claim as their primary residence) and non-homestead (commercial properties, businesses, second homes or rental properties or other land).
The change ordered by the Legislature garnering the most attention is a reduction in what cities and counties will collect on homesteaded property. (Note: The Legislature revised DeSantis’ proposal, which would have also reduced taxes that support schools. So the new rules would not apply to school taxes.)
Winter Park City Hall
Winter Park collected $19.8 million in 2025 from homesteaded properties. If voters approve the proposed increase to the homestead exemption from $50,000 today to $250,000 in 2028 then those collections would drop to about $14.2 million, according to Randolph’s projections. The reduction would first be felt, to a lesser extent, by cities and counties in 2027 when the homestead exemption would jump to to $150,000 before increasing to the full $250,000 the following year.
So that’s a loss of $5.6 million based on today’s numbers or a 28% reduction in collections on homesteaded properties. The overall hit to the city’s tax roll appears closer to 12% because stormwater fees ($6.3 million), tangible property taxes ($1 million on equipment and furnishings in businesses or rental properties) and non-homesteaded property taxes ($21.2 million) aren’t affected by the change to homestead exemptions.
This year the city spent $5 million more just to cover basic cost-of-living and 3% merit raises for city staff, including more competitive wages for police and additional emergency call center staff as the city took on dispatch duties for Maitland.
The entire capital improvement budget for the Community Development Agency, which is funded entirely through property taxes, totaled $5.7 million. That included $3.2 million to fix drainage and infrastructure problems on West Fairbanks Avenue, Canton Avenue and the MLK Park basin. Another $2.5 million went to the Park Avenue Refresh project, which includes new street lighting, sidewalks, landscaping, underground infrastructure and other work.
The rebuilding of Fire Station 62 on Lakemont Avenue is estimated at $5.8 million, a project the city put off again this year because it didn’t have the funds.
Mayor Sheila DeCiccio predicted noticeable cuts will be made if the new proposal goes into effect.
“This will be devastating,” DeCiccio said after the Legislature’s vote. “We will be assessing what services the city may have to cut.”
The entire city budget is $233 million this year. That includes the two utilities that fund themselves with a combined nearly $100 million in what customers pay for water and electric service.
Beyond that, the single biggest source of revenue for the city is property taxes.
Those taxes are the biggest contributor to the city’s almost $90 million general fund, which is responsible for all of the front-line services like police and fire rescue (the two biggest expenses), parks and recreation and public works.
“Property taxes are continuing to row the boat for the city’s fiscal picture, rising 7.6% and accounting for 44% of General Fund revenue,” reads the budget document from last year. “This stabilizing force is what keeps most city services humming. Its rate of growth is sufficient to support the existing level of city services, but it is limited in what it can provide in excess of just staying on course.”
So is that all?
No. There’s more. The ballot amendment would also hamstring cities and counties by limiting future growth in the amount of taxes collected on non-homesteaded properties.
The cap on annual assessment increases for those properties — anything from a Publix grocery store to an Amazon warehouse to a vacation home — would drop from 10% to 5%.
That represents future savings for billion-dollar corporations and less future revenue for local governments to use for police, fire rescue, roads and everything else property taxes pay for.
Growth in property values is how a city like Winter Park, which has enjoyed a brisk real estate market for years, has managed to increase its budget without raising the tax rate for 18 years.
A little more than half of the city’s total ad valorem collections or about $21.2 million come from non-homesteaded properties owned by everyone from small business owners to deep-pocketed corporations who will save money as a result of the new cap.
The exact amount of future unrealized growth is hard to quantify, city officials say.
But this chart from the budget shows the importance of the increase in assessed values year to year:
But even before the new ballot amendment was in play, city officials were beginning to warn of a softening in that growth and the need for belt-tightening.
“The General Fund is seeing continued increases in property tax revenue due to increasing valuations in existing real estate which has traditionally been the primary support of the majority of the growth in revenues over time,” the budget reads. “However, this revenue source is continuing its slowing trend and could indicate tighter years ahead.”
If approved, the new cap will exacerbate that picture.
What else does the ballot amendment do?
In addition to reducing revenue cities and counties have to work with, the measure would also restrict how that money is spent.
Property taxes would only be able to pay for items that fall in one of the following buckets, according to a Senate press release:
Public safety, including law enforcement, fire service, and emergency medical service
Education and public schools (additional funds beyond operational expenses covered by school board taxes)
Road and bridge construction and maintenance, stormwater control, and other infrastructure projects
Natural resource projects, including flood control measures
Retirement benefits of local government employees
Bond obligations
Operations and administration of county officers and commissioners and municipalities, and approved expenditures
Assistant City Manager Michelle del Valle, who will be in the top role next year when the changes begin to take effect after City Manager Randy Knight retires, said city staff is already starting to assess what may or may not fit into those categories. Some items in question, she said, are considered core services that residents have come to expect.
“The biggest one that we’re going to have to start working on is Parks and Recreation,” she said. “But also the library … all of our cultural partnerships.”
The Winter Park Library & Events Center.
This year the Parks budget is nearly $15 million. The city spent about $2.4 million on its library this year. And more than $500,000 went to cultural and nonprofit organizations through the general fund and the CRA such as Mead Botanical Gardens, Winter Park Historical Association, Winter Park Day Nursery, United Arts, Blue Bamboo, Polasek Museum, Enzian Theater, Heritage Center, Welbourne Day Nursery and Winter Park Playhouse.
DeCiccio said the attempt to cut local budgets is an extension of a longstanding effort by Tallahassee to chip away at the power of local governments.
“Where are people supposed to go?” DeCiccio asked. “Are they supposed to go to the state to complain about potholes in the roads? It’s very, very frustrating.”
The proposed ballot amendment, she said, strips voters of a layer of autonomy and accountability to closest to where they live.
It’s more often the city and county commissioners vs. state officials who run into residents at the grocery store or in the school pick-up line and hear their frustrations about uneven sidewalks or broken streetlights, a desire for more shade trees or a plea to help the arts.
“What about libraries? What about playgrounds? They are taking away our ability to fund these items,” DeCiccio said. “We have the No. 1 children’s library in the state that’s now open seven days a week. How are we going to keep paying for that?”
What can cities do in response?
Even before the proposal to cut property taxes, cities like Winter Park began raising prices on everything from after-school programs run by the parks department to stormwater fees and electric rates to compensate for rising costs in recent years.
For example, at the most recent City Commission meeting, commissioners approved a contract extension for Waste Pro, which provides garbage collection. The city doesn’t make money off the contract — it’s a pass through — but residents’ monthly rates have shot up from $14.99 in 2022 to $22.22 in 2025.
And residents could pay more in other ways.
Cities and counties could choose to increase the millage rate on properties — something Winter Park has avoided for 18 years — to blunt the effect of the proposed changes.
“If county and municipal governments raise millage rates to recoup the lost revenue, that would result in higher property taxes on the portion of the value of homestead properties that remains taxable, as well as on the many properties that do not qualify for the substantially higher exemption, including the properties of new Florida residents and second homeowners, commercial properties (including apartment complexes), and industrial and agricultural properties,” reads an analysis from the conservative-leaning Tax Foundation. “This would make Florida’s property tax system far less neutral and disincentivize the purchase of certain classes of property.”
Or, the foundation argues, policymakers could choose to increase the sales tax to help make up for lost property taxes.
“Since Florida’s tax structure includes no individual income tax, sales taxes and property taxes are the primary sources of state and local tax revenue,” the group said. “Replacing the lost property tax revenue with sales tax revenue would require substantially higher local and/or state sales tax rates, a sweeping expansion of the sales tax base (likely to more than just final personal consumption), or a combination of these approaches.”
Winter Park doesn’t set the sales tax or the local gas tax. That’s done by a combination of state and county officials. But it does share in sales and gas tax revenue, though that revenue is far less than property tax revenue for the city.
Winter Park’s 2026 budget included $5.6 million from sales tax and just under $1 million from the local option gas tax, a fraction of the more than $41 million it received in property taxes.
What happens next?
As with any ballot amendment, there is likely to be litigation and fights over the ballot language.
But once it makes the November ballot, at least 60% of voters must approve it in order for it to pass. That’s a heavy lift in Florida.
In 2024, there were six constitutional amendments on the Florida ballot and all but two failed to capture the required 60% approval. That was the year an amendment to legalize recreational marijuana and to limit government interference with abortion received 56% and 57% of the vote, respectively, but fell short of the 60% threshold.
But an amendment related to property tax exemptions passed with 66% of the vote. It provided for an annual inflation adjustment for the value of the homestead property tax exemption that applies to non-school taxes.
Two years earlier, though, a 2022 amendment to increase the homestead exemption for public service workers including teachers, law enforcement officers and others failed with 59% of the vote.
What about Winter Park’s next budget?
City officials say they still plan to present a proposed budget to the City Commission in July on the typical schedule.
The next budget is based on the 2026 tax roll and would not be impacted by the proposed changes, which aren’t set to take effect until next year if they win voter approval.
But officials say they are cognizant of what potentially lies ahead and are taking that into account.
The City Commission usually begins to hear public input on the budget in August and must adopt it by the end of September before the start of the next fiscal year in October.
Historic Preservation Disagreements Pile Up: Spend Money on a Consultant? Offer Tax Incentives?
The City Commission this week touched off what is likely to be a contentious debate over how — or even if — property owners should be encouraged to place historical assets on a local register to help protect them from demolition
May 29, 2026
By Beth Kassab
Preservationists pleaded with City Commissioners this week over what is likely to be only the first disagreement as Winter Park endeavors to save more houses from the bulldozer: Whether the Historic Preservation Board should be able to spend money on a consultant as it works to make recommendations tasked by the commission.
The request was simple: Hire an expert to help evaluate what’s been lost, what’s still worth saving and how to go about keeping more old homes off the rubble pile.
But preservation debates in the city have a long tradition of drawing entrenched camps in which one side argues private property rights trump all else and that public dollars shouldn’t be used on private assets while another side says each teardown irreversibly erases a piece of the charm, eclectic architecture and history that makes Winter Park so unique and desirable.
The latest round of preservation talks are complicated by the backdrop of the Florida Legislature’s special session next week that could result in a proposal to significantly decrease property taxes collected by local governments such as Winter Park to pay for needs such as police, fire rescue, parks, roads and more.
“I don’t think history can just live on a plaque or marker, it has to be seen and observed,” said Commissioner Elizabeth Ingram, who said during the discussion at Wednesday’s commission meeting that she supported hiring an expert to focus on the task of forming a historic preservation strategy for the city. “I don’t believe the Historic Preservation Board can do this on their own … they could put out a call for guidance and start planning for creating this position for historic preservation.”
Ingram noted that other cities have designated historic preservation officers with specialized expertise that members of the volunteer advisory board may not have.
Mayor Sheila DeCiccio almost immediately threw water on that idea.
“But how are we going to pay for a person, Commissioner Ingram? Where do we get the money?” DeCiccio asked.
Earlier in the meeting the mayor said the property tax reform being pushed by Gov. Ron DeSantis could mean, “We’re not going to have any more taxes … I don’t know how we are going to keep the roads going … keep City Hall going?”
Betsy Owens, executive director of Friends of Casa Feliz, countered that local governments make funding choices all the time when something matters.
“We find room in the city budget for a lot of things we value,” she said. “We spent $200,000 today to undo a mistake that was made on the golf course … Heaven help us if we can’t find a few thousand dollars to hire a respected consultant to guide us through this process and help us out of this quandary.”
Earlier this month the city shut down the Winter Park Nine after the wrong chemical was applied to the course, killing off the grass. On Wednesday the commission approved a $197,000 course maintenance contract for four months — or nearly $50,000 per month. City Manager Randy Knight said the purpose was to test whether staff should farm out golf course maintenance or keep it in house.
The longtime owners are selling the property and the contracted buyer is seeking special permission to split the lot in two so that the Merrywood portion can be sold off again and a new home can be constructed on a new lot next to it.
Without a buyer willing to restore Merrywood, it appears destined for the bulldozer whether or not the Planning & Zoning Board approves the lot split request at a hearing scheduled for next Tuesday at 5 p.m. And, so far, no buyer has emerged, Owens said.
People who showed up to speak on the matter at Wednesday’s meeting lamented the potential loss.
Carolyn Gould, who has lived in the city 70 years, said she recalls riding her bike down Palmer Avenue past Merrywood and the wonder it inspired even from the driveway gate.
“When it’s bulldozed it’s gone,” she said. “You need to walk through those rooms and look through those windows … the moldings and appointments are just one-of-a-kind … I’m on fire about this for some reason. We have to get busy and do something.”
Daryl Carter, who purchased and renovated a Gamble Rogers house on Palmer Avenue in recent years, said most people who looked at the home considered tearing it down.
“We did not,” he said. “Our house doesn’t have a historic designation. We did what we did voluntarily … we love beauty, but we’re also private property owners and believe in private property rights. I hope this board will take that into consideration and not take private property rights from owners.”
While some cities designate properties as historic without an owner’s consent, no one is suggesting such a policy change in Winter Park.
The discussion is more about how to offer additional incentives to urge more people to seek historic designation if their property qualifies. The city has the ability in its code already to provide tax exemptions to historic properties, though no one appears to be taking advantage of that as of now, said Planning & Zoning Director Allison McGillis. The city also offers a 50 percent matching grant for renovation work that qualifies, up to $18,000, she said.
The local historic register and designated historic districts do not outright prohibit demolition in Winter Park. But the request must be approved by the Historic Preservation Board. The board does not have control over interior renovations — only major changes to the facade of the structure.
Those who designate their homes often receive special permission for variances during a renovation that wouldn’t be allowed in a non-historic structure and they are also allowed to add accessory dwelling units (such as a small rental or mother-in-law suite) to their properties.
“We have the easiest to skirt around ordinance in the entire state of Florida,” said Aimee Spencer, a former member of the Historic Preservation Board who lives in a 102-year-old house. “Even Quincy, Florida out does us in their preservation standards,” she noted of the Panhandle town of fewer than 8,000 people.
She said Winter Park needs better rules and also education against misinformation circulating about historic homes such as how they are ineligible for financing or insurance.
“I have a typical mortgage and homeowners insurance with State Farm,” she said. “It’s not a problem to insure or finance.”
Kelsey Wolfe, who serves on the preservation board, noted the board is all volunteers with related skills and a passion, but not necessarily the professional expertise needed to prepare a comprehensive strategy to shift the direction from tear downs to preservation.
“We’ve spent countless hours making changes to the ordinance already and we are waiting on a survey that hasn’t been done in 20 years and we brainstorm every meeting and work session about the very thing you’re officially charging us with,” Wolfe said. “The vast majority of our ideas and requests don’t get implemented because we don’t have the help or the budget.”
She noted that the McGillis, the staff person devoted to the Historic Preservation Board also oversees all of Planning & Zoning for the entire city.
The commission remained unmoved, however, and voted 4-0 to charge the advisory board with formulating recommendations without, at least for the time being, any additional resources.
WinterParkVoiceEditor@gmail.com
CORRECTION: This story has been updated to reflect Winter Park’s current property tax exemption and matching grant program for historic properties that qualify.
Preservation Advocates Say Winter Park Must Do More to Save Historic Homes
With three John Gamble Rogers II homes under threat of demolition this year, advocate says dwindling assets should serve as ‘wake up call’
May 14, 2026
By Beth Kassab
With three homes designed by James Gamble Rogers II currently under threat of demolition, historic preservation advocates pleaded with the City Commission on Wednesday to make meaningful changes to the way Winter Park protects its historic assets.
Betsy Owens, executive director of Friends of Casa Feliz and granddaughter of Gamble Rogers, said she hopes the potential loss of three significant houses — all more than 85 years old — in a single year will serve as a “wake up call” for the city to strengthen its historic preservation ordinance. She said the city’s ordinance is among “the weakest in the state.”
“These are not anonymous old buildings,” Owens said. “They are irreplaceable works by the architect who more than any other helped define the visual character of Winter Park.”
None of the three homes are listed on the city’s historic register, meaning there is no protection from demolition. The register is voluntary and many owners deliberately opt to keep homes off the register under the theory that the home will be worth more without demolition restrictions.
Owens, and other advocates who spoke at the meeting, including Jack Rogers, said it’s time for Winter Park to get serious about preservation.
They are recommending the commission consider adding incentives such as property tax breaks or rehabilitation help for people who list their homes on the register. They are also calling for new ideas such as an investment fund to help with purchasing and then reselling historic homes to people who are willing to invest in and preserve them.
Mayor Sheila DeCiccio recommended a discussion about potential changes be added to the next City Commission meeting on May 27 and the other commissioners agreed. The commission would likely send the matter to the Historic Preservation Board for further evaluation before making a final decision on changes.
The homes currently under threat are:
1020 Palmer Avenue, also known as Merrywood, which is under active demolition permit and could be demolished by the end of May. The home is one of the largest and most ornate in the dwindling collection of Gamble Rogers homes. Tara Tedrow, the prospective buyer who has the property under contract, facilitated the demolition permit in March and is also asking the city to amend its comprehensive plan to allow the lakefront property to be split into two lots. Under that scenario, she said, she would attempt to find a buyer interested in restoring Merrywood while her family could build a new home on the other portion of the property. A Planning & Zoning Board hearing on the request was delayed at Tedrow’s request until June. “Despite enormous public interest and dozens of interested investors touring the property, no buyer has yet emerged able to reconcile the nearly $10 million (estimated) asking price with the substantial restoration needs of the house, conservatively estimated at more than $3 million,” Owens said in an email to supporters.
250 Virginia Drive sits on a large lot overlooking Lake Virginia. The home was sold last year for $2.6 million and a demolition permit was filed by the new owner last month. The home is considered an example of the Colonial Revival style with strong New England influences, including shaker shingles.
617 Interlachen Avenue is possibly “the most eclectic and artistically ambitious of Rogers’ Spanish Eclectic residences. There is no demolition permit filed yet, but Rogers said the home is expected to go up for sale soon and in one of the city’s most expensive neighborhoods. “History has shown that when the dirt beneath a home becomes worth many multiples of the structure itself, it is time for that home to get its affairs in order,” she said.
Blue Bamboo Pulls AI School Sublease from City Commission Agenda
The president of the arts group that rents the old library from the city of Winter Park said it will “take a pause” on the idea of renting out the second floor to a private school
May 12, 2026
By Beth Kassab
The leader of the Blue Bamboo Center for the Arts said on Tuesday morning that he would pull a request from this week’s City Commission agenda a request to rent out the second story of the group’s venue to an artificial intelligence-driven private school.
The sublease request, first reported by the Voice on Friday, prompted a number of community questions about whether the for-profit school to be run through a Winter Park couple’s disaster relief foundation met the original intent of creating an arts hub in the old city library building.
“The Blue Bamboo Board of Directors has decided to take a pause on the agenda item at this time,” read a message from President Jeff Flowers to the group’s supporters. “We feel that the issues the sublease raises will be better addressed by requesting a city work session where the best use of the facility can be addressed.”
Todd Weaver, a former city commissioner who was instrumental in securing the lease for Blue Bamboo during his tenure, is now the group’s vice president.
The Commission, including Weaver, voted 4-1 in July of 2024 to lease the building to the small nonprofit arts venue. Mayor Sheila DeCiccio was the only no vote after she questioned the group’s financial sustainability. Before the Blue Bamboo won the lease, Rollins College was aiming to repurpose the building into a new art museum.
The venue opened in the summer of 2025 and just months later Blue Bamboo founder and musician Chris Cortez died from brain cancer.
But questions about the future use of the building were already mounting. Just months before Cortez died Central Florida Vocal Arts, which had partnered with Blue Bamboo to secure the city lease as well as a nearly $1 million Orange County grant for the venue and was planning to occupy the second floor, walked away from the deal when the two groups couldn’t come to terms.
That left Blue Bamboo without a sublease to help meet a higher rent obligation to the city that is set to begin in August.
Blue Bamboo’s lease payment is scheduled to increase from $132,000 a year to $276,000 a year in three months.
The proposed sublease to Matthew and Paige Wideman’s Love & Life Foundation was the first concept for the second floor to be brought to the commission since Central Florida Vocal Arts opted against moving forward with Blue Bamboo.
The draft lease calls for the foundation, which says it specializes in helicoptering in aid after hurricanes and other disasters, to pay an annual rent of $198,000 for the second floor, or about $18 per square foot for 11,000 square feet.
The lease between Blue Bamboo and the city calls for the second and third floors of the building to be renovated within two years for “arts education, recording studio and local non-profit use.”
Matthew Wideman told the Voice he planned to use the space to start a location of Alpha School, a for-profit model of private school founded in Austin, Texas that has been lauded by the Trump administration and where tuition is expected to be about $45,000 a year.
The Alpha model calls for students to spend about two hours a day on core subjects such as math using AI-led instruction. Human staff members — known as “guides” rather than teachers — spend the rest of the day helping students develop business, public speaking and other project-based skills.
“The school shall not have more than 50 students, and will not accept school vouchers funded by the State of Florida for those students’ tuition or expenses,” according to a copy of the lease posted with the City Commission agenda for Wednesday’s meeting.
The idea, Flowers told the Voice last week, was to use the music and arts expertise of Blue Bamboo to help instruct students at the school.
City spokeswoman Clarissa Howard said commissioners will now discuss on Wednesday whether to hold a potential work session about the lease at a later date.
Big Changes Felt on Park Avenue with 'Disruptive' Construction Underway
George’s Cafe owner says the ‘Refresh’ project is hurting business while other sections of the avenue are undergoing a transformation with high-profile closures and new construction for the Rollins art museum and, potentially, a city garage
May 11, 2026
By Beth Kassab
On a recent afternoon, George Paul checked over receipts for the day’s business at George’s Cafe, known for piled-high sandwiches and from-scratch cookies bigger than a fist.
“I lost money today,” said Paul, who has operated the shop in the former Brandywine’s Delicatessen spot on North Park Avenue for six years and, before that, at a location on Lee Road. “And it’s not just today … the sidewalks are torn up. There’s barricades. For our older clientele, it looks hazardous. Our business is down by two-thirds.”
George’s sits in the middle of the first block — from Swoope to Canton avenues — of Park Avenue closed last month as part of the city’s three-year, estimated $8.5 million effort to refurbish underground wires and piping, contain tree roots, upgrade streetlights to a higher-tech model, smooth sidewalks and install other aesthetic changes such as new garbage cans and planters.
Paul said he’s adjusted his hours during the construction to account for fewer patrons.
While city officials see the project, known as the Park Avenue Refresh, as a much-needed antidote for aging infrastructure, merchants are bracing for a temporary dose of pain.
George’s Cafe during construction for the Park Avenue Refresh. (This photo and above photo courtesy of the city of Winter Park.)
“It’s going to impact every business, including ours, at some point, but it’s just one of those things,” said Alan Chambers, co-president of the Park Avenue District and vice president of operations for John Craig Clothier, which operates two stores on the avenue. “We all lived through the major refresh of 30 years ago and it brought tremendous benefits to Park Avenue. When it’s all said and done, it costs us all a little bit of frustration.”
A New Era for the Avenue
Brand Melville opened on Park Avenue in April.
Chambers was referring to the last major series of infrastructure projects on Park, including bricking over paved sections of the road, which started in the mid-1990s when phones didn’t yet have cameras, the O.J. Simpson trial dominated television and the old Winter Park Mall on U.S. Highway 17-92 still stood before it was demolished to make way for Winter Park Village.
Now, the latest refresh project is coinciding with a number of monumental changes that will usher in a new era for the oldest and most celebrated shopping and dining district not just in the city, but across Central Florida.
Park Avenue counted 3 million visitors last year, up from 2.1 million in 2020 and 2.7 million in 2019 before the pandemic. The data is based on consumer tracking software used by the city government that captures unique U.S.-based cellphone signals, meaning some international visitors may not be included in the totals.
Customers check out the newly opened Brandy Melville on Park Avenue on a recent afternoon.
Last month, the opening of Brandy Melville, a popular Gen Z brand known for its minimalist aesthetic and beachy vibe, brought lines of customers waiting to enter. Videos posted to TikTok showed a queue of mostly teen and college-age women wrapping around the corner at Morse Boulevard to check out the store, which has been criticized as discriminatory toward some body types for its policy of selling just one size per style (generally the equivalent of a small).
On a recent weekday, 23-year-old Valentina Orive said she drove 45 minutes to shop there — a short distance compared with the three hours she once drove to visit other locations in South Florida.
“I like the quality of the clothes a lot,” she said, noting the Winter Park store, which replaced the Lily Pulitzer, is larger than the others she has visited, except for one in New York City. “They just have really good basics.”
Love Brandy or hate it, some other merchants took advantage of the foot traffic, Chambers said, with at least one nearby boutique, Through the Looking Glass, offering discounts to customers who showed a Brandy Melville receipt.
Longtime Institutions Face Change
Meanwhile, other institutions along the avenue are calling it quits.
Miller’s Hardware, the longest continuously operating family-owned business there, will shut its doors for good sometime during the second quarter of this year after more than 80 years, setting the stage for redevelopment of the block fronting Fairbanks Avenue.
Stephen Miller, owner and grandson of the founder, said he made the decision for multiple reasons that “took the wind out of my sails.” His son, Clay — whom he anticipated would take over the business — died unexpectedly in 2019 at age 29 and, he said, the business simply doesn’t generate enough revenue compared with what the property is worth.
As for what he will do with the prime piece of real estate, Miller isn’t yet saying.
Miller’s Hardware has been run by the same family for more than 80 years. It plans to close in the coming months.
“The future of the property is to be determined,” he said. “I’m weighing options.”
Miller said he would like to see the current batch of city commissioners consider allowing “more density” as aging buildings are redeveloped.
“The plumbing on Park Avenue kept me in business … that stuff is old,” he said. “The City Commission just needs to let there be more density so they can support rebuilding a lot of places people love.”
Behind the Scaffolding
One spot now undergoing an interior demolition and rebuild is 310 Park Ave. S., where the longtime eatery of the same name closed at the end of 2024.
Dyar McComb of Great American Land Management Inc. declined to be interviewed about the work underway at the building owned by the Holler family through a company called PA Partners LLLP, which owns multiple buildings along the avenue.
Signs beneath the construction scaffolding out front display the logo for Oak & Stone, a concept by Artistry Restaurants, the Winter Park-based group that also operates Boca and The Chapman on Park.
Chambers said some people were surprised by the work on the block between New England and Lyman avenues, but the exterior of the 100-year-old building will remain the same.
Construction scaffolding covers the front of 310 Park Avenue South, a sign of more changes to come on the avenue.
“There wasn’t anything inside that looked historic, and I’m not sure if anything had ever been replaced, so it’s going to be a wonderful change for that building,” he said. “The Hollers are going to do a good job on that. They are tremendous partners in the city and in the district.”
People forget, he noted, that “at one point that entire space was an Olive Garden and then Fat Tuesday.”
That was before the first refresh project three decades ago, when part of the street was still paved rather than brick and no one had even heard of Y2K much less streaming in 4K.
More Changes on the Horizon
With the latest refresh project well underway, even larger changes are afoot beyond shifting storefronts.
City officials are considering building a three-story garage behind City Hall to ease parking frustrations with 120 new public parking spaces on top of the 145 required for city employees and operations.
An architectural rendering shows the exterior of a new Rollins Art Museum.
And Rollins College is constructing a new 30,000-square-foot art museum across from The Alfond Inn, just blocks from Park Avenue, that will also alter the equation for foot traffic and parking.
The museum is set to open in 2028, the same year the third and final phase of the Park Avenue Refresh — from New England to Fairbanks avenues — is scheduled to take place.
George’s Block to Reopen
As for George’s, Paul said he is grateful his catering business is doing well but wishes the city would do more construction work at night or on weekends, when it would be less disruptive to his breakfast-and-lunch cafe.
Clarissa Howard, who is leading the refresh project, said some work related to the stormwater system will be done at night, particularly when workers must close the entire street.
Each block closure, which includes shutting down one lane of traffic with detours, will last about four weeks, she said.
“There’s always going to be disruption with any kind of construction, but we’re not there for months and months at a time,” Howard said. “It’s four weeks and the infrastructure we’re putting in will last four decades.”
She said the stretch in front of George’s is set to reopen this week and the project will continue moving block by block south toward Fairbanks Avenue.
“We’re definitely hurt,” Paul said. “I don’t know … I wish there was a solution to this. I can’t imagine what it’s going to be like when they go down the street.”
Family Envisions AI-Driven Alpha School for Second Floor of Blue Bamboo
A sublease agreement will be considered by the City Commission next week as the nonprofit music venue looks to fill space before a rent increase later this year
May 8, 2026
By Beth Kassab
The second floor of the Blue Bamboo Center for the Arts, which leases the former library building from the city, could soon house a location of the private, artificial intelligence-driven Alpha School.
The school was praised last year by the Trump administration as a model for education, and tuition is expected to be about $45,000 a year.
The school would operate through the Love & Life Foundation, a nonprofit that delivers disaster aid and is led by Winter Park residents Matthew and Paige Wideman.
Matthew Wideman said that mission overlaps with the for-profit Alpha School because he views K-12 public education as being in crisis.
“What I would argue is our mission is lifting up the hands of those that are oppressed or impacted, and we look at the education system as a disaster,” Matthew Wideman told the Voice.
He said the school’s innovative approach is one potential solution and that the second floor of the old city library is an ideal setting for a school designed to “empower and prepare children for the world of tomorrow.”
The Alpha model was founded in Austin, Texas, where students spend about two hours a day on core subjects such as math using AI-led modules. Human staff members — known as “guides” rather than teachers — spend the rest of the day helping students develop business, public speaking and other project-based skills.
U.S. Secretary of Education Linda McMahon visited the school last year and said she was “blown away” by the model, according to news reports. Her visit came after President Donald Trump signed an executive order promoting the use of AI in schools.
“They use a more tailored program to find out what the child’s interests and talents and gifts are and help them find that at a young age,” Paige Wideman said. She added that she appreciated the school’s emphasis on “EQ,” or emotional intelligence.
The Widemans, who have five children ranging in age from 2 to 13, said they personally fund their foundation and could potentially provide scholarships for the school, which is known for tuition of about $45,000 a year or, in some cities, more.
Many private schools in Florida accept public vouchers or public education dollars that can be spent at private schools.
But a provision in the draft lease would prohibit the school from accepting vouchers.
“The school shall not have more than 50 students, and will not accept school vouchers funded by the State of Florida for those students’ tuition or expenses,” according to a copy of the lease posted with the City Commission agenda for next Wednesday’s meeting.
The vouchers — commonly known to parents as Step Up for Students scholarships — are at the center of a new lawsuit filed by Florida’s largest teachers union and several parents, including Orange County School Board member Stephanie Vanos, who represents Winter Park and has three children of her own.
The lawsuit alleges the program violates the constitution because the state now sends more than $5 billion in public money to private and charter schools through vouchers while not requiring those schools to follow the same standards as traditional public schools.
Matthew Wideman and Jeff Flowers, who runs Blue Bamboo, said the restriction on vouchers was requested by the city.
City spokeswoman Clarissa Howard said city staff did not advise on the voucher issue or initiate the requirement.
Wideman said his core business is real estate. He holds an ownership interest in Truist Plaza, the downtown Orlando high-rise, among other ventures through The Wideman Company LLC.
He also said his foundation has partnered with Starlink, part of SpaceX, to restore communications after hurricanes and other disasters.
Alpha School also operates a location in Brownsville, Texas, near Elon Musk’s new rocket hub and city known as Starbase. The school also has campuses in five other states, including Florida locations in Palm Beach Gardens and Miami, according to the Alpha website.
Under the draft lease, the Love & Life Foundation would have the right to enter into agreements with third parties such as Alpha to provide operational, management and administrative services for the school.
Wideman said the school would benefit from Blue Bamboo’s performing arts infrastructure and expertise, including its stage, which students could use to practice public speaking and other skills.
Flowers, who helped finance Blue Bamboo for years and took over operations last year after founder Chris Cortez died, said the organization’s performers could serve as music teachers and provide other technical instruction for students.
The lease between Blue Bamboo and the city calls for the second and third floors of the building to be renovated within two years for “arts education, recording studio and local non-profit use.”
Flowers said the sublease is an important part of Blue Bamboo’s financial picture because its lease payment to the city is scheduled to increase from $132,000 a year to $276,000 a year in August.
The proposed lease with Wideman’s foundation calls for annual rent of $198,000 for the second floor, or about $18 per square foot for 11,000 square feet.
Last year, another nonprofit, Central Florida Vocal Arts, walked away from a sublease agreement with Blue Bamboo after becoming dissatisfied with the terms.
Flowers said the building’s third floor remains available for sublease.
He said he has invested both personal funds and Orange County grant money into improvements, including a staircase, a new elevator, a refurbished air-conditioning system and a new fire alarm system. Blue Bamboo received about $900,000 last year through a county grant program funded by the tourist development tax collected on hotel rooms.
Flowers said the venue’s performance calendar is mostly booked through January.
“We’re profitable,” Flowers said. “We’re paying the rent and the utility bill and keeping up with expenses.”
WinterParkVoiceEditor@gmail.com
Update: This story has been updated to include a response from city spokeswoman Clarissa Howard.
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