Demolition clock starts on Merrywood as preservation push builds

One Historic Preservation Board member called it a “defining moment” for Winter Park

March 12, 2026

By Beth Kassab

The clock is ticking on the fate of Merrywood.

The sprawling Winter Park estate — among the largest and most ornate homes designed by architect James Gamble Rogers II — could be demolished in as soon as 90 days unless preservationists can find a buyer willing to save it.

A demolition application has been filed for the property at 1020 Palmer Ave. by owners Cathleen and Raymond Gilmer, siblings who inherited the estate from their parents, who bought the 1939 lakefront home in 1977. The 3.67-acre property overlooks Lake Osceola.

City officials have limited power to stop the demolition because the home is not listed on Winter Park’s Historic Register. But because it appears in the Florida Master Site File, city rules automatically trigger a 90-day delay before a demolition permit can be issued, giving preservationists time to seek alternatives.

That countdown prompted a packed discussion before the city’s Historic Preservation Board this week that drew a who’s who of Winter Park names.

Everyone seemed to have an opinion — from Marc Hagle, known for traveling to space with his wife aboard a Blue Origin suborbital flight and for constructing what is currently the city’s largest home, a 31,000-square-foot residence just a few doors down from Merrywood, to local preservation advocates and the granddaughter of the home’s architect.

“I think, as a community, this is one of those defining moments,” said Margie Bridges, a former city commissioner who now serves on the Historic Preservation Board. “… this is one of those special homes … We have a short time to rally and step up and take care of this in any way that it’s most efficient for the buyer and preserves something special in our community.”

Tara Tedrow, the prospective buyer who has the property under contract, facilitated the demolition permit and is also asking the city to amend its comprehensive plan to allow the lakefront property to be split into two lots.

Under that scenario, she said, she would attempt to find a buyer interested in restoring Merrywood while her family could build a new home on the other portion of the property.

A Planning & Zoning Board hearing on the request was delayed at Tedrow’s request until June.

In the meantime, she said filing the demolition application was intended to start a conversation about saving the home.

“The purpose was to get folks here and to have folks talk about this so that we could at least open a 90-day window to get some creative solutions to see if there is something that can be done to preserve the house,” Tedrow told the board.

Toward the end of the meeting she added: “I want to be clear: we’re not tearing the house down on Day 91. My husband and I have no intention of actually demo-ing the house ourselves.”

Betsy Owens, executive director of preservation advocacy group Friends of Casa Feliz, said she is working to help Tedrow tap a network of preservationists and reach potential buyers for Merrywood in Florida and across the country.

Owens, the granddaughter of the home’s architect who recently walked through the property, said the structure is significant for its “remarkable level of craftsmanship” in masonry, plaster, wood and tile that would be “nearly impossible to replicate.”

“Merrywood contributes to the historic character of our community, helping to tell the architectural story of what makes Winter Park such a distinctive and economically prosperous place,” she said. “Together with our cherished tree canopy and chain of lakes, our beautifully designed historic homes are the goose that laid the golden egg in Winter Park … Once a building is gone, it’s gone forever. Preservation is not about nostalgia. It’s about stewardship of the cultural resources that define a community.”

She noted past examples of the community rallying to save homes threatened with demolition such as Casa Feliz, which was moved to sit on the Winter Park Nine, and the Capen House, which was floated across the lake to find a permanent home as an event space next to the Polasek Museum.

Christy Knobloch, executive director of the Winter Park History Museum, said preserving real pieces of the past is just as important as preserving archives.

“It’s hard to tell the stories of what it was in a photograph,” she said.

Other speakers noted the potentially high costs of restoring such a home and questioned whether such a buyer exists.

“I think we all love the house,” said John Skolfield, chairman of the Historic Preservation Board. “Most of us find the house very attractive and we want to find a way to preserve it. But these are big dollars, and these are not my decisions. These are the people with the big dollars who can purchase a property like this.”

Hagle, the one-time astronaut who recently completed years of construction at 926 Palmer Ave. after tearing down an older home there, said he has mixed feelings about saving the house but opposes the idea of splitting the lot.

“We just had a party at our house this last weekend — I apologize for the noise if y’all heard that,” he said. “But we had people from all over the world for a fundraiser at the house, and they all commented how gorgeous the city of Winter park is. And that’s who we are … Unfortunately, we’re in a difficult situation because it’s not fair to the homeowner to be burdened with having to save a house that was built in the 1920s that is difficult to repair.”

Aimee Spencer, a former member of the Historic Preservation Board, said she is weary of the narrative that maintaining an old home is too costly.

“I implore this board to begin to help dismantle the myth that preservation of our historic resources is cost prohibitive,” Spencer said. “It is disingenuous to continue the comparison of high quality restoration and rehabilitation to the type of new construction that generally plagues this city. Certainly there are high quality new builds, but on a whole, the comparison is that of apples to steak. True masterpieces are few and far between in Central Florida, and certainly we have already lost many. This remains an attempt at an end run around to produce two empty parcels. Lot splits are not a right in the city of Winter Park, but rather at the discretion if value is added to the city.”

The 90-day demolition delay is expected to expire around the end of May. The Planning & Zoning Board is scheduled to consider the comprehensive plan amendment that could allow the lot split in June.

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