The days may be numbered for Winter Park’s Merrywood House.
A sharply divided City Commission on Wednesday got a commitment from the historic home’s owners to delay demolition while it attempts to grant them an exception to the city’s long-standing policy against splitting up lakefront lots.
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But Cathy Gilmer told commissioners she and her brother plan to tear down the house regardless of whether they’re allowed to divide up the property.
“The truth of the matter is that every day the house remains standing costs money we don’t have, falls into further disrepair and is not contributing anything to the community,” Gilmer said with emotion in her voice. “Demolition is the only viable path forward.”
Commissioners voted 3-2 to back an amendment to the comprehensive plan — tailored to apply only to 1020 Palmer Avenue — that would allow splitting the 3.67-acre lot along Lake Osceola. Mayor Sheila DeCiccio joined Commissioners Craig Russell and Kris Cruzada to pass it, while Commissioners Elizabeth Ingram and Warren Lindsey dissented.
Before the vote, Ingram asked about requiring Gilmer and her co-owner, her brother Raymond Gilmer, to delay demolition until after the required second reading expected later this summer. The city must send comp plan amendments to the state, which has 30 days to review them, so the required second reading will likely happen within 45-60 days.
Tara Tedrow, the land-use attorney seeking the lot split, told commissioners she could get approval for the delay. Tedrow, who wants to buy half the land to build a home, said she has worked to find a buyer who’d save Merrywood, but to no avail.
“My request was never meant to pit any of you against historic preservationists or me against historic preservationists,” she said. “If anything, this has raised an issue that we shouldn’t maybe talk about historic homes at the last hour of these things.”
Merrywood is the largest home designed by the city’s famed architect, James Gamble Rogers II. The Spanish-style home built in 1939 has more than 7,000 square feet of living space. It’s estimated fewer than 30 homes he designed remain standing in the city.
The Gilmers have a permit to demolish Merrywood, but have held off since last year while the search for a buyer who’d preserve it was underway.
Cathy Gilmer said Merrywood was her family’s home since 1976, when she was 6, until her mother died last year. Over the final years of her parents’ lives they discussed the fate of the house many times, she added, and the property was always meant to be what their parents left them as a gift after passing away.
“We respect the fact that our parents intentionally did not designate the house historic and we will not pursue a historic designation,” Gilmer said. Placement on the register would have offered it some protection from demolition.
The proposed comp plan change commissioners ultimately approved had two amendments offered by Cruzada and agreed to by Tedrow. One reduces the combined square footage of homes built on the two lots from 40,000 to 30,000. The other would require the home on one lot (and possibly both) follow certain architectural designs to be designated during second reading.
Without those changes, owners could potentially build a 55,991-square-foot house on the land. The city’s largest house, just down the street at 916 Palmer Avenue, is about 40,000 square feet.
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Lindsey said he couldn’t support the proposal because lot splitting is a major issue in the city and shouldn’t be rushed.
“This is not a trivial vote that we’re taking, this goes to the heart of the character and culture of Winter Park,” he said.
The city’s prohibition against splitting lakefront lots dates back to the 1990s and was put in place to protect community character and natural resources along the city’s lakes.
Ingram, arguably the most vocal supporter of saving the house, pointed out how the city gets nothing in return for granting this exception to its longtime policy.
“I’m only interested in considering any lot split … if the city and our residents get something back,” she said. “We’ve been getting emailed so much about it and so many people, including myself, want to save that.”
However, DeCiccio said as much as the community wants the house preserved, it’s just not going to happen.
“In the past, when Casa Feliz was saved … that was done through private funds,” she said of another Rogers house moved to a new location to become a museum and events venue. “In this situation, not one person … has come forward to write a check to help maintain the house, to help purchase the house.”
She noted how the city will get results later this year from a $75,000 survey of all houses over 50 years old that could help save other historic homes in the future.
Mick Night, of Sotheby’s International Realty, told commissioners that of the more than 100 people shown Merrywood, only about 25 could afford it and no offers were received.
“None of us wants to see a Gamble Rogers come down,” Night said, but the house is in such poor condition it would cost around $8 million or more in renovations on top of land costs. The Orange County Property Appraiser’s website lists a 2025 market value of $7.29 million for the property, the latest year available.
After the meeting, Betsy Rogers Owns, executive director of Friends of Casa Feliz, said she was very disappointed by the commissioners’ decision.
“It’s hard to say you’re serious about historic preservation and not take opportunities like that when they present themselves,” said Owens, granddaughter of Gamble.
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