Winter Park’s historic Merrywood House can’t be demolished at the moment due to permitting issues, but a surprise $15 million sale this week means there’s likely nothing standing in the way if the new owners want their own permit to bring in the wrecking ball.
And whatever leverage the city commission may have had to save the 1939 mansion — by using its power to approve splitting the lot as a prospective buyer had sought, or to reject their request — may be a moot point now that the entire property has been sold. That is true even though a vote on the split remains on the commission agenda for Wednesday.
Allison McGillis, city director of Planning & Zoning, said by email that the former owners, siblings Cathy and Raymond Gilmer, applied for a demolition permit Feb. 26 but never completed any of the necessary steps to get it. Their application expires Wednesday.
“There is still a process they need to complete before the demolition can occur,” McGillis said. “In other words, it’s not as though the new owners could come in and demolish the property tomorrow.”
The city said Sorenson Construction, of Winter Garden, the contractor listed on the application, requested an extension Friday morning, but the owners still need to complete a revised ownership affidavit before that can happen.
McGillis couldn’t say how long the permitting process for demolition would 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 Gilmers sold the 3.67-acre estate along Lake Osceola on Monday 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, lists its registered agent as Orlando law firm Cypress Row Advisors and one of its senior attorneys, Carla DeLoach, is listed as manager.
An exclusive look inside Winter Park’s historic, imperiled Merrywood House
The Orlando Sentinel has not been able to reach either of the Gilmers for comment despite repeated attempts by phone and email. Cathy Gilmer has said Merrywood was her family’s home from 1976, when she was 6, until her mother died there last year.
The agenda for Wednesday’s City Commission meeting still includes what would be the 2nd, and final, vote required to approve a proposed amendment to the comprehensive plan tailored to permit splitting the lot at 1020 Palmer Avenue.
An email DeLoach sent Thursday afternoon to McGillis requested, on behalf of the owners, that commissioners delay the issue until the Oct. 14 meeting. Attempts Friday to reach DeLoach by phone and email for comment were not successful.
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.
Attorney Tara Tedrow, with Orlando-based Lowndes Law, sought the lot-split amendment because she said she had a contract on the property with plans to build a home on part it. The deed of sale for the new owners was prepared by one of her colleagues.
Tedrow has declined comment to the Sentinel, but has told the city she is not connected to Lake Osceola Holdings. She said the buyers were a couple who surfaced after the first vote on the proposed amendment — but were fine closing on the land without a final decision.
A view from the formal dining room toward the breakfast room in Merrywood. (Joe Burbank/Orlando Sentinel)
The boathouse on Lake Osceola at Merrywood, the 7,300-square-foot, 3.7-acre estate designed by renowned architect James Gamble Rogers II, located on Palmer Avenue in Winter Park, Tuesday, June 30, 2026. (Joe Burbank/Orlando Sentinel)
There is a vintage hot tub at Merrywood. (Joe Burbank/Orlando Sentinel)
A view from the backyard of Merrywood in Winter Park. The historic home was sold Aug. 17, 2026, for $15 million to Lake Osceola Holdings LLC, but the people who actually own it now aren’t known. Preservationists have been working for months to save the iconic home. The plans the new owners have for it are not known. (Joe Burbank/Orlando Sentinel)
The pantry in Merrywood, the 7,300-square-foot, 3.7-acre estate designed by renowned architect James Gamble Rogers II, located on Palmer Avenue in Winter Park, Tuesday, June 30, 2026. (Joe Burbank/Orlando Sentinel)
A view of the shoreline and boathouse facing Lake Osceola at Merrywood. (Joe Burbank/Orlando Sentinel)
The living room of Merrywood in Winter Park has an applied wooden molding intended to simulate ornate coffered panels. The door left of the fireplace leads to the loggia, while arched openings lead to the reception room at left and the enclosed terrace at right.c(Joe Burbank/Orlando Sentinel)
A view of the living room from the reception room in Merrywood. (Joe Burbank/Orlando Sentinel)
A view from the backyard of Merrywood, the 7,300-square-foot, 3.7-acre estate designed by renowned architect James Gamble Rogers II, located on Palmer Avenue in Winter Park, Tuesday, June 30, 2026. (Joe Burbank/Orlando Sentinel)
A view of the pool deck facing Lake Osceola at Merrywood, the 7,300-square-foot, 3.7-acre estate designed by renowned architect James Gamble Rogers II, located on Palmer Avenue in Winter Park, Tuesday, June 30, 2026. (Joe Burbank/Orlando Sentinel)
The sunken patio in the back of Merrywood. (Joe Burbank/Orlando Sentinel)
Merrywood, photographed on June 30, 2026, is located on Palmer Avenue in Winter Park. (Joe Burbank/Orlando Sentinel)
The principal bedroom in Merrywood. (Joe Burbank/Orlando Sentinel)
A view from the entry hall into the loggia, which is a covered corridor or gallery, in Merrywood, the 7,300-square-foot, 3.7-acre estate designed by renowned architect James Gamble Rogers II, located on Palmer Avenue in Winter Park, Tuesday, June 30, 2026. (Joe Burbank/Orlando Sentinel)
A path of red brick pavers leads from the patio of Merrywood to the pool and pool house. (Joe Burbank/Orlando Sentinel)
A view from the side yard of Merrywood, the 7,300-square-foot, 3.7-acre estate designed by renowned architect James Gamble Rogers II, located on Palmer Avenue in Winter Park, Tuesday, June 30, 2026. (Joe Burbank/Orlando Sentinel)
A path of red brick pavers leads from the patio of Merrywood to the pool and pool house. (Joe Burbank/Orlando Sentinel)
A view of the enclosed terrace from the living room in Merrywood, the 7,300-square-foot, 3.7-acre estate designed by renowned architect James Gamble Rogers II, located on Palmer Avenue in Winter Park, Tuesday, June 30, 2026. (Joe Burbank/Orlando Sentinel)
Carpeted stairs in Merrywood, the 7,300-square-foot, 3.7-acre estate designed by renowned architect James Gamble Rogers II, located on Palmer Avenue in Winter Park, Tuesday, June 30, 2026. The banister on the wall is metal covered in velvet. (Joe Burbank/Orlando Sentinel)
The entry hall in Merrywood. (Joe Burbank/Orlando Sentinel)
Merrywood sits on 3.67-acres. The estate is one of only 30 or so homes James Gamble Rogers II designed that remain standing in Winter Park. (Joe Burbank/Orlando Sentinel)
The elevator in Merrywood has a scissor gate and walls covered in a green-and-white floral Damask design. (Joe Burbank/Orlando Sentinel)
Carpeted stairs in Merrywood, the 7,300-square-foot, 3.7-acre estate designed by renowned architect James Gamble Rogers II, located on Palmer Avenue in Winter Park, Tuesday, June 30, 2026. The banister on the wall is metal covered in velvet. (Joe Burbank/Orlando Sentinel)
A demolish notice posted by the City of Winter Park at Merrywood. (Joe Burbank/Orlando Sentinel)
A vintage intercom device in the kitchen of Merrywood, the 7,300-square-foot, 3.7-acre estate designed by renowned architect James Gamble Rogers II, located on Palmer Avenue in Winter Park, Tuesday, June 30, 2026. (Joe Burbank/Orlando Sentinel)
The main staircase in the entry hall in Merrywood has ornate wrought-iron railings and balusters with a velvet-covered handrail on the wall. (Joe Burbank/Orlando Sentinel)
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A view from the formal dining room toward the breakfast room in Merrywood. (Joe Burbank/Orlando Sentinel)
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 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.
Morgan said he plans to attend the commission meeting, adding he believes the community would benefit from greater transparency regarding the sale and the new owners.
“Ultimately, we must preserve this historic home and protect it for the community,” he said.
While the lot split would boost the value of the land, it would also reduce the size of the homes that could be built. 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.
Mayor Sheila DeCiccio told commissioners during their Aug. 12 meeting that she was frustrated over a lack of information on the property and asked McGillis to bring together interested buyers, the Gilmers, historic preservationists and others involved in the issue. The property was sold days later, to her surprise.
She declined comment ahead of Wednesday’s meeting.
A search on the city’s permitting self-service portal, for permits issued since Aug. 20, 2025 for demolition of single-family residences turned up 106 results showing a status of “complete,” meaning the structure is fully removed. It showed 14 in which the demolition is incomplete — including another Gamble-designed home at 250 Virginia Avenue.
The house at 250 Virginia Drive is seen Thursday, June 11, 2026. The 2,714-square-foot home was designed by Winter Park’s famed architect James Rogers Gambles II. Built in 1939 on Lake Virginia, it is an example of Colonial Revival architecture. The city issued a demolition permit for the house Aug. 13, 2026. (Ricardo Ramirez Buxeda/Orlando Sentinel)
Among the most recent are for four homes built between 1939 and 1968 which sold for between $1.7 million and $3 million, the Gamble home among them. The others are at 516 Henkel Circle, 633 Balmoral Road and 1205 Mayfield Avenue.
Betsy Owens, executive director of Friends of Casa Feliz and one of the people working to save Merrywood, plans to attend the commission meeting and address commissioners.
“We feel like whether they vote today or next week, or they vote in a couple of months, we don’t feel the lot split should be granted … without receiving something in return,” said Owens, the granddaughter of Gamble. “What we believe the city should receive in return is its designation as a historic asset.”