Preservation Advocates Say Winter Park Must Do More to Save Historic Homes
With three John Gamble Rogers II homes under threat of demolition this year, advocate says dwindling assets should serve as ‘wake up call’
May 14, 2026
By Beth Kassab
With three homes designed by James Gamble Rogers II currently under threat of demolition, historic preservation advocates pleaded with the City Commission on Wednesday to make meaningful changes to the way Winter Park protects its historic assets.
Betsy Owens, executive director of Friends of Casa Feliz and granddaughter of Gamble Rogers, said she hopes the potential loss of three significant houses — all more than 85 years old — in a single year will serve as a “wake up call” for the city to strengthen its historic preservation ordinance. She said the city’s ordinance is among “the weakest in the state.”
“These are not anonymous old buildings,” Owens said. “They are irreplaceable works by the architect who more than any other helped define the visual character of Winter Park.”
None of the three homes are listed on the city’s historic register, meaning there is no protection from demolition. The register is voluntary and many owners deliberately opt to keep homes off the register under the theory that the home will be worth more without demolition restrictions.
Owens, and other advocates who spoke at the meeting, including Jack Rogers, said it’s time for Winter Park to get serious about preservation.
They are recommending the commission consider adding incentives such as property tax breaks or rehabilitation help for people who list their homes on the register. They are also calling for new ideas such as an investment fund to help with purchasing and then reselling historic homes to people who are willing to invest in and preserve them.
Mayor Sheila DeCiccio recommended a discussion about potential changes be added to the next City Commission meeting on May 27 and the other commissioners agreed. The commission would likely send the matter to the Historic Preservation Board for further evaluation before making a final decision on changes.
The homes currently under threat are:
- 1020 Palmer Avenue, also known as Merrywood, which is under active demolition permit and could be demolished by the end of May. The home is one of the largest and most ornate in the dwindling collection of Gamble Rogers homes. Tara Tedrow, the prospective buyer who has the property under contract, facilitated the demolition permit in March 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. “Despite enormous public interest and dozens of interested investors touring the property, no buyer has yet emerged able to reconcile the nearly $10 million (estimated) asking price with the substantial restoration needs of the house, conservatively estimated at more than $3 million,” Owens said in an email to supporters.
- 250 Virginia Drive sits on a large lot overlooking Lake Virginia. The home was sold last year for $2.6 million and a demolition permit was filed by the new owner last month. The home is considered an example of the Colonial Revival style with strong New England influences, including shaker shingles.
- 617 Interlachen Avenue is possibly “the most eclectic and artistically ambitious of Rogers’ Spanish Eclectic residences. There is no demolition permit filed yet, but Rogers said the home is expected to go up for sale soon and in one of the city’s most expensive neighborhoods. “History has shown that when the dirt beneath a home becomes worth many multiples of the structure itself, it is time for that home to get its affairs in order,” she said.
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Historic Preservation takes big $ to make happen. Whether that comes from the public or private sector, it is required. So if it is so important to many of our residents and members of the City Commission, I propose a very simple first step in raising $ for this effort…sell the old library and put those $ in a historic preservation fund to be used to help compensate owners or future buyers of these properties, thus insuring these special homes are preserved. Otherwise, the City is in no position to put up enough $ to make a difference.
The challenge is deciding what is, and what is not, an architectural gem. And who decides? Simply being designed by a particular architect should not be enough.
If a house is enough of a gem, someone will buy the property and take care of it.
I do not support the City using hard earned citizen tax dollars to be in the house buying and selling business.