The lakefront land where Winter Park’s historic Merrywood mansion stands was sold to a mystery company for $15 million this week in a move that stunned those trying to save it from demolition.
The sale, the largest ever for a single lot in the city’s history, could potentially allow the new owner to build a 55,991-square-foot house on the land under existing ordinances. The previous owners had sought permission to split the lot, which might make it easier to preserve Merrywood, but it’s not clear whether next week’s scheduled hearing on that request now will proceed.
“If the home is preserved, I’m ecstatic,” said attorney Matt Morgan, who had unsuccessfully offered $12 million for the property. “If the home is torn down for profit, it’s going to be incredibly discouraging.”
Documents filed Wednesday with Orange County show the owners of the 3.67 acres along Lake Osceola, siblings Cathy and Raymond Gilmer, sold it to Lake Osceola Holdings LLC. The entity, registered with the state June 10, has its registered agent listed as Orlando law firm Cypress Row Advisors and one of its senior attorneys, Carla DeLoach, listed as manager. The firm states it provides concierge-level tax planning services.
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.
The Gilmers have a permit to demolish Merrywood, but have held off since last year while a search was underway for a buyer who could preserve it. Cathy Gilmer has said it was her family’s home from 1976, when she was 6, until her mother died last year. The Sentinel has not been able to reach either Gilmer for comment.
Orlando-based attorney Morgan, who lives in Winter Park, offered $10 million in 2025 for the entire property, upping it to $12 million in July, and said he would spend his own money to preserve the house. He said he was told the Gilmers weren’t interested in his first offer and never received a response to his latest.
An exclusive look inside Winter Park’s historic, imperiled Merrywood House
After learning of the sale from the Orlando Sentinel, he said it’s not promising for the future of the mansion at 1020 Palmer Avenue, which would cost millions to renovate.
“It’d be very difficult for someone to make a rational economic investment with that property at that purchase price while preserving the home unless somebody truly loves the area and the home,” said Morgan, who works at Morgan & Morgan, the firm started by his father John Morgan. “We had hopes of reaching a deal at the directive of the city this week and having an agreement in place before the hearing took place next week.”
The deed of sale filed with the county says it was prepared by attorney Jason Williams, with the Lowndes firm based in Orlando. His colleague, attorney Tara Tedrow, previously had sought an amendment to the city’s comprehensive plan to allow splitting the land. She has said she had a contract to buy a vacant portion of the land with plans to build a home on it.
Neither DeLoach or Williams returned emails or phone calls seeking comment. Tedrow declined to comment.
Mick Night, of Premier Sotheby’s International Realty, has consulted for about a year with the Gilmers on selling the property and did not return emails, calls or texts seeking comment.
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 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)
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)
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. (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 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 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)
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 path of red brick pavers leads from the patio of Merrywood to the pool and pool house. (Joe Burbank/Orlando Sentinel)
City commissioners gave preliminary approval June 24 on a 3-2 vote for the comp plan amendment Tedrow sought, which was tailored to apply only to the Merrywood land. But Mayor Sheila DeCiccio told commissioners during their Aug. 12 meeting that she was frustrated over a lack of information on the property and directed Allison McGillis, the Planning & Zoning director, to bring together interested buyers, the Gilmers, historic preservationists and others involved in the issue.
McGillis learned of the sale from the Sentinel on Wednesday and said she was still working to organize the meeting requested by the mayor. “We had no idea,” she said.
The split-lot amendment is set to come back to the commission Wednesday for final consideration, but McGillis said it will likely be tabled. She said Tedrow told her she is not connected to Lake Osceola Holdings.
She said she also heard from Tedrow the buyers were a couple who surfaced after the first vote on the amendment — but were fine closing on the land without a final decision.
Betsy Owens, executive director of Friends of Casa Feliz and one of the people DeCiccio wanted at that meeting, was also surprised to learn of the sale from the Sentinel and echoed Morgan’s sentiments on Merrywood’s future.
“I hope that whoever bought it is open to the idea of preserving this part of Winter Park history, but I’m not optimistic,” said Owens, the granddaughter of Gamble. “I suspect this does not mean good things for Merrywood.”
Lakefront lot splits, which vastly increase a property’s value, are rare in Winter Park. The city’s prohibition against splitting them dates back to the 1990s and was put in place to protect community character and natural resources along the city’s lakes.
Without a lot split, someone who purchases the entire property — such as the mystery buyers — could build a home even bigger than the city’s largest house, just down the street at 916 Palmer Avenue, which is about 40,000 square feet. While the lot split would boost the value of the land, it would also reduce the size of the homes that could be built.
Commissioner Elizabeth Ingram, who opposed the comp plan amendment and is arguably the commission’s most vocal supporter of saving Merrywood, said she knew little of the sale but expects to have more information for Wednesday’s meeting.
“I’m so shocked and caught off guard,” Ingram said.