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.

Owens’ group is currently trying to find a private buyer for Merrywood, a large estate on Lake Osceola designed by architect James Gamble Rogers II that is one of three of the architect’s works facing likely demolition this year.

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.

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CORRECTION: This story has been updated to reflect Winter Park’s current property tax exemption and matching grant program for historic properties that qualify.