While no one has heard publicly from the new owners of Winter Park’s historic Merrywood estate, they told the city through a representative that they want a permit to demolish it.
The initial application for a permit filed by the former owners was extended this week for 90 days — allowing more time to complete the requirements to obtain it. The city said it received authorization to do so from the new owner’s representative.
Meanwhile, city commissioners Wednesday unanimously tabled until Oct. 14 the second, and final, vote on a controversial proposed lot split for the Merrywood land in the tony area along Lake Osceola.
Mayor Sheila DeCiccio said at the beginning of the meeting the city has no idea what’s next for the property.
“Apparently there’s new owners of the property and we’re not sure what they’re going to do, whether they’re going to keep Merrywood, designate it (as historic), tear it down,” DeCiccio said. “So this will give us time to get a handle on what’s going to be happening with it.”
The new owners had asked the city to delay the second vote until October.
Siblings Cathy and Raymond Gilmer sold the 3.67-acre property last week for $15 million to Lake Osceola Holdings LLC in a move that stunned those working to save the house from demolition. The entity — registered with the state June 10, two weeks before the commission’s first vote on the lot split issue — lists its registered agent as Orlando law firm Cypress Row Advisors and one of its senior attorneys, Carla DeLoach, as its manager. The identity of the actual buyers are unknown.
The Gilmers applied for a demolition permit Feb. 26, but never completed any of the steps required to issue it — such as various inspections and paying about $1,500 in fees. Sorenson Construction, the Winter Garden contractor listed on the application, requested an extension Friday morning. The city’s permitting portal showed $150 was paid Tuesday for the extension on the application, which would’ve expired Wednesday.
Allison McGillis, the city’s Planning & Zoning director, has said she doesn’t know how long the permitting process will take, but once all required documentation and pre-demo inspections are approved, it would be issued upon payment of fees. In general, landowners have the right to demolish structures on their land once permits are filed and paid for, and Merrywood has no historical designation to get in the way of that.
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. It’s estimated fewer than 30 homes he designed remain standing in the city. Commissioners recently tasked their historic preservation board with recommending ways to improve preservation efforts, as iconic homes are torn down to make way for new ones in a city where vacant land is scarce.
An exclusive look inside Winter Park’s historic, imperiled Merrywood House
Multiple attempts to reach DeLoach, the new owners representative, by phone and email for comment were not successful.
Attorney Tara Tedrow, with Orlando-based Lowndes Law, originally requested the lot-split amendment earlier this year because she said she had a contract on the property with plans to build a home on part it. Although the deed of sale was prepared by one of her colleagues, Tedrow has told the city she’s not connected to Lake Osceola Holdings.
The sale, the largest-ever for a single lot in city history, could potentially allow the owner to build a 55,991-square-foot house on the land under existing ordinances. It’s about 300 feet from the city’s largest home at 916 Palmer Avenue — which is about 40,000 square feet.
Orlando-based attorney Matt Morgan offered $10 million in 2025 for the entire property and upped it to $12 million in July, adding that he’d spend his own money to preserve the house. He was told the Gilmers weren’t interested in his first offer and did not receive a response to his second.
Betsy Owens, executive director of Friends of Casa Feliz and one of the people working to save Merrywood, attended the meeting with plans to speak. However after the lot-split issue was tabled, Owens, the granddaughter of Gamble, said she would wait to address commissioners when they take it up in October.