Winter Park’s iconic Merrywood house now seems headed for demolition, but over the course of a three-hour city commission meeting Wednesday, a slim hope emerged: that a portion of it could become a facade for the new owner’s guest house.
Commissioners had been scheduled to take the final vote on a proposal to split the 3.67-acre lot at 1020 Palmer Avenue, which had been considered one of the city’s few areas of leverage to save the home from the wrecking ball.
Instead, they delayed a decision until the Nov. 11 meeting, a delay meant to provide time for City Attorney Kurt Ardaman and Planning & Zoning staff to work with the new owner, businessman Steve Lockwood, toward a compromise that could save part of the house.
Lockwood’s attorney Jason Searl told commissioners Lockwood was open to discussions. But earlier in the meeting, he said Lockwood’s plan for the land involved tearing Merrywood down without further delays.
“What happens if we receive a no vote today on this request? A no vote is the demolition application filed with the city to be performed,” Searl said initially.
Wednesday’s commission meeting was the latest twist in the tortuous path to Merrywood’s ultimate fate, which still remains uncertain. The 7,300-square-foot Spanish-style home built in 1939 is the largest residence designed by the city’s famed architect, James Gamble Rogers II. The city said 50 buildings designed by him — commercial and residential — remain standing in Winter Park.
Lockwood, who last year bought Orlando-founded drinkware brand Corkcicle, purchased the property on Lake Osceola in August for $15 million from siblings Cathy and Raymond Gilmer. He initially bought the property secretly through a mystery corporation, Lake Osceola Holdings LLC, and the later revelation of the transaction stunned those who’ve been working for many months to save the house from demolition.
The Merrywood sale, the largest-ever for a single lot in city history, could potentially allow Lockwood to build a 55,991-square-foot house on the land under existing ordinances. The city’s current largest home is about 40,000 square feet.
Searl said Lockwood’s initial vision involves dividing the land into two lakefront lots where he and a friend could both build homes for their families. Searl said two reports filed Monday with the city attest to the mansion’s significant structural damage, necessitating demolition.
But in pursuit of the needed city comprehensive plan amendment to split the lot, he said Lockwood was willing to, at his own expense, work to save or restore part of the existing structure where feasible. A section of Merrywood could then be incorporated into a new structure on the property, such as a guest house or pool house.
Commissioner Elizabeth Ingram, arguably the commission’s most vocal advocate for saving Merrywood, said she wasn’t willing to rely on Lockwood’s “good-faith effort” to save part of it.
“Our comprehensive plan is not just a collection of suggestions that we set aside when someone presents us with a compelling financial opportunity for themselves or an alarming hypothetical scenario,” Ingram said.
Steve Lockwood, left, the new owner of the land where the iconic Merrywood mansion sits, speaks toward Betsy Rogers Owens, executive director of Friends of Casa Feliz and granddaughter of James Gamble Rogers II, during the Winter Park City Commission meeting on Wednesday, Oct. 14, 2026. Next to him is Jason Searl, an Orlando real estate attorney. (Brian Bell/Orlando Sentinel)
She said she’s never been categorically opposed to dividing the property, but wants legally binding protections stating what parts of the home and how much square footage would be saved.
Commissioner Craig Russell, however, said that while he’s all for historic preservation — and believes Merrywood can be renovated — he is also a strong supporter of property rights.
“There’s a lot of pocket-watching going on around here,” Russell said. “Who am I to tell anybody how to spend their money?”
Vice Mayor Kris Cruzada said he supported adding language to the proposal requiring partial preservation and defining exactly what that is.
“I’m trying to find a path to some level of preservation or lose it all together,” Cruzada said. “We’re in an unfortunate set of circumstances.”
Allison McGillis, director of the city’s Planning & Zoning department, also suggested language specifying the square footage or percentage of the existing structure that would be retained and maintained by current and future owners through a deed restriction.
But Searl said he and Lockwood couldn’t support it.
They instead returned with a printout of a photo of Merrywood showing two portions surrounded by blue lines from a pen.
Orlando real estate attorney Jason Searl writes on a printed image of the Merrywood mansion in Winter Park displayed on screens during the Winter Park City Commission meeting on Wednesday, Oct. 14, 2026. Searl was doing it during discussions on saving the center part of the home and attempt to save the other part on behalf of the new owner, Steve Lockwood. (Brian Bell/Orlando Sentinel)
“Steve and his family are willing to make a good-faith attempt to save the front facade, a minimum of these two areas,” Searl said, referring to the image on the screens, “if the policy is approved and the split goes in place tonight.”
He said if at any point during that effort it becomes impractical, impossible, part of the house falls down or the family doesn’t like the way it will look, Searl would bring the issue back the commission.
Commissioners could then rescind, withdraw or waive it under the presumption that Lockwood had made a good-faith attempt, he argued, and if the split is denied he’d have to wait a year to apply again for it under city codes.
Ardaman advised commissioners they could make the lot split contingent upon preserving a portion of the front — and if Lockwood is not able to accomplish that, he doesn’t get his lot split.
But Commissioner Warren Lindsey, another consistent proponent of saving Merrywood, said he couldn’t vote for such a vaguely-worded proposal.
An exclusive look inside Winter Park’s historic, imperiled Merrywood House
“I am grateful for everything you did, I’m grateful for Mr. Lockwood coming here … I’m not willing to vote in the blind on a picture with blue lines on it,” Lindsey said. “This is something that is meaningful to the citizens of Winter Park.”
Ultimately, Searl told commissioners he and Lockwood agreed with tabling the vote for further discussion. “This is very significant to us … and we look forward to continuing the conversation on Nov. 11,” he said.
Ten people spoke during public comment, with the majority opposing demolition. Some shared their own experiences restoring and renovating historic homes and how they found it hard to believe Merrywood couldn’t be saved. Others said the city shouldn’t limit what Lockwood does with his property.
Betsy Rogers Owens, executive director of Friends of Casa Feliz and granddaughter of Gamble Rogers, was one of those who spoke against demolition.
“I’m not without hope, but I’m frustrated,” Owens said Thursday. “The devil’s in the details. We’d love to see a compromise, we don’t want the perfect to be the enemy of the good here.”