A historic Winter Park home on Lake Osceola built by the city’s most-famous architect could be demolished soon, unless there’s a buyer who wants to preserve the nearly 70-year-old house and is willing to navigate a complicated combination of city rules and residents’ interests.
The Merrywood House is the largest home designed by architect James Gamble Rogers II, who also designed the storied Casa Feliz. Casa Feliz also faced demolition but was saved from the wrecking ball 25 years ago when city residents raised money to move the structure to city-owned land.
Merrywood, built in 1940, is a large Spanish-style home, with more than 7,000 square feet of living space. The house features a grand entry hall and a covered porch with sweeping views of Lake Osceola. It sits on a nearly four-acre lot and is currently unoccupied.
The current owners have filed a demolition request, but the home also has a prospective buyer, who wants to split the lot, build a new home on half the property and sell Merrywood to someone who wants to preserve and restore it.
Winter Park’s comprehensive plan, however, prohibits splitting lakefront lots and getting such a plan approved requires an amendment to the city code. The city’s planning and zoning board is to consider the request in June and then make a recommendation to city commissioners, who have final say.
In the meantime, preservationists are worried.
Betsy Rogers Owens, the executive director of the Friends of Casa Feliz, which helped save that property, said estate homes like the Merrywood property are “a dying breed” in Winter Park.
“They’re underappreciated for what they give the city in terms of its sense of place, its sense of scale, its beauty,” said Owens, who is also the granddaughter of the architect.
The Merrywood property at 1020 Palmer Ave. in Winter Park on Tuesday, March 24, 2026, was built by James Gamble Rogers, the same architect responsible for Casa Feliz. Local residents and preservationists are advocating for the house’s preservation, with concerns that it will be demolished unless they find a buyer for the property. (Rich Pope/Orlando Sentinel)
She said losing the house –– which she describes as a showplace –– would be akin to “losing the goose that laid the golden egg in Winter Park.”
Rogers designed many Rollins College buildings as well as the Florida Supreme Court building in Tallahassee, according to the Winter Park Library, which called him “Winter Park’s most revered architect.”
The Merrywood house is not on the city’s historic register, however, a designation which would have offered it some protection from demolition.
The current owners, siblings Raymond Gilmer and Cathleen Gilmer, could not be reached for comment.
Tara Tedrow, the property’s prospective buyer, filed the demolition request on behalf of the owners but said she does not want to knock down the old house. Instead, she hoped the demolition notice would get the community’s attention and help find a new owner for Merrywood itself.
Tedrow, a local land-use attorney, said allowing the Merrywood lot to be split would not impact other lakefront properties and would work given the size of the property.
On Merrywood’s lot, someone could build a house as big as 56,000 square feet –– a size that would be “out of character with the city’s desire to maintain scale, charm and compatibility of residential development,” she said via email. Her plan would allow Merrywood to remain and a new house to be constructed on a still-sizeable parcel.
A notice of demolition is posted at the Merrywood property at 1020 Palmer Ave. in Winter Park on Tuesday, March 24, 2026. The home was built by James Gamble Rogers, the same architect responsible for Casa Feliz. Local residents and preservationists are advocating for the house’s preservation, with concerns that it will be demolished unless they find a buyer for the property. (Rich Pope/Orlando Sentinel)
Allison McGillis, the city’s director of planning and zoning, said the policy prohibiting lakefront lot splits is in place to protect community character and natural resources along Winter Park’s lakes.
Though the house is not a historic site, it is listed as a historical resource so the demolition request had to be presented to Winter Park’s Historic Preservation Board as an information item. The board could not deny the request, however.
At a March 11 meeting, board members said they want to see the house preserved, especially because it was designed by Rogers and connected, therefore, to the city’s history.
Board member Margie Bridges said saving the house will need the efforts of the city, the community and Tedrow.
“We are a historic community and if we start pulling those threads out of the fabric of this community finally at some point, we’ve destroyed it,” Bridges said. “And I don’t believe any of us want to do that.”
John Bill, the chairman of Friends of Casa Feliz, is hoping for a repeat of Casa Feliz’s story.
That historic house was set to be razed and replaced with a 12,000-square-foot mansion in 2001 until preservationists and the city intervened to relocate the house.
The 750-ton building was placed onto 20 dollies and moved onto city property where it was ultimately restored and opened as a museum and events venue. Friends of Casa Feliz was formed to save the house and raised over $1.5 million in donations and corporate sponsorships.
The organization now operates the Casa Feliz Historic Home Museum.
Bill, who got a chance to tour Merrywood recently, said the two-story house stands out in “quality, magnitude, design and location.”
The home features original tile, oak floors and decorative ironwork and masonry. “I don’t really know that there are any other houses in the same league in this,” Bill said.
But most importantly, he said the home honors the architectural past of Winter Park. These historic houses are “what makes Winter Park, Winter Park,” he added.
Owens said the Merrywood home is showing its age but someone with appreciation for historic architecture could turn the house into a “showplace.”
“If there’s somebody out there who says, ‘Yeah, I’d love a chance at seeing that house to see if I could buy it and restore it’…. Now’s the time,” she said.