Lot Split Request Puts Future of Gamble Rogers Estate in Question

Lakefront lot splits are against Winter Park policy. But the prospective owner of the largest lot on the city’s esteemed chain of lakes says the alternative could be worse — a residence so large it dwarfs the Library & Events Center

Feb. 7, 2026

By Beth Kassab

The fate of 1020 Palmer Avenue — a once-grand home and among the largest and most ornate ever designed by James Gamble Rogers II (think velvet-covered handrails) and known in recent years as “Merrywood” — appears to hinge on whether a unicorn buyer emerges to save the property.

Such a feat would take not only millions of dollars, but also approval from city officials to break one of Winter Park’s cardinal development rules: No lakefront lot splits allowed.

Tara Tedrow, the prospective buyer who has the property under contract, is asking for an exception to that rule to allow the 3.67-acre lot — the largest property on the picturesque Winter Park Chain of Lakes — to be divided into two lots on Lake Osceola. Each lot, she said, would be at least 150 feet wide and 1.5 acres or larger.

Zillow estimates the property at $12.1 million while other estimates, such as Redfin, list it at $6.4 million.

Tedrow, a land-use and cannabis law attorney at Lowndes, could then potentially sell the lot with the existing home and build a new home for her family on the newly created lakefront lot. The exception would be written in such a way that it would apply only to her lot and no others, according to city staff, because the lot Tedrow wants to purchase is the only one large enough.

While she told the Planning & Zoning Board earlier this week that she believes the currently vacant home is beyond repair, she said she is open to talking with buyers interested in restoring the 7,000-square-foot structure, which dates back to 1940.

She also met with Betsy Owens, granddaughter of Gamble Rogers and leader of the Casa Feliz Historic Home Museum — a Gamble Rogers home and now a popular event space that was famously moved from Interlachen Avenue to just off the ninth fairway of the Winter Park Nine 25 years ago after it was threatened with demolition.

“I’m certain if I’m not in the picture, that the house will get torn down,” Tedrow told the P&Z board earlier this week of the Palmer Avenue home.

The house at 1020 Palmer Avenue is not on the city’s historic register because the longtime owners chose to keep it off. It could be destroyed with a simple demolition permit. However, the property is listed on the Florida Master Site File, a state database of historical and cultural resources, which means the city’s Historic Preservation Board could delay a demolition request for 90 days to allow time to consider alternatives or ways to preserve pieces of the home.

The P&Z board voted 4–2 on Tuesday to grant Tedrow’s request to delay the hearing on the lot split until June — so far, there is no demolition request — to give her time to see whether anyone comes forward who may be interested in restoring the property.

“We appreciate the opportunity to present this case to the city and to hear from our neighbors and members of the historic preservation community,” Tedrow told the Voice. “Having grown up in Winter Park, I appreciate just how unique and beautiful the city is. As I am expecting my third baby in three years, I want more than ever to move back to Winter Park.”

Alex Stringfellow, Bill Segal, David Bornstein, and Charles Steinberg voted in favor of granting the continuance.

Jason Johnson, chairman of the P&Z board, and board member Michael Dick voted against continuing the hearing on the lot split. Both expressed skepticism that a lot split — which would require a change to the comprehensive plan that governs how the city will develop in coming years — should be granted.

The rule states that a property owner cannot divide a lakefront parcel into two and build a house on each one. Such splits would increase density and development along the shorelines of the city’s lakes and decrease the diversity of lot sizes central to the city’s unique character.

The only exception in the plan — which does not apply in this case — is when there is a lakefront lot with a house that is historically designated and older than 1950, and the lot split does not create a new lakefront lot, said Planning & Zoning Director Allison McGillis. In such a case, which occurred last year with another Gamble Rogers house on North Park Avenue, one lot remained on the lakefront while the newly created lot was not on the water.

McGillis told the board she has heard from residents in the area who have concerns about a potential lot split.

“I’ve gotten questions about the fate of the house,” she said. “Most people I’ve talked with want to preserve the Gamble Rogers house because there are not many of them left.”

While splitting the lot does not guarantee that the home would be preserved, Tedrow said a potentially worse outcome could be on the horizon if a lot split is not granted.

Because of the size of the lot, a buyer could demolish the old home and would be entitled to build a new house as large as 56,000 square feet.

“The largest home in the city has a gross floor area of over 36,000 square feet — this 3.67-acre property is legally entitled to have a home 55% larger,” Tedrow told the Voice in an email. “To further put this into perspective, the city’s new library and event space total around 50,000 square feet. The home that could be built at 1020 Palmer Avenue under today’s Comprehensive Plan would be larger than both buildings combined on the city’s library campus and would dwarf every home in Winter Park.”

Such a house would also dwarf the home of Marc and Sharon Hagle, who spent years constructing the largest residence in Winter Park — the one Tedrow mentioned that is 36,000 square feet — just a few doors down Palmer Avenue.

“I think there are some buyers out there who might do that,” she told P&Z members. “I’m not that buyer. So maybe we flip this to somebody else …”

Owens, who also attended the meeting, said she appreciates that Tedrow came to Casa Feliz and is considering ways to find a buyer who might be willing to restore the home.

“We appreciate her willingness to work with us,” Owens said.

The property was most recently the home of Dr. Raymond Gilmer, an orthopedic surgeon who died in 2020 at age 90, and his wife, Sarah, who purchased it in 1977.

The home is now vacant and owned by the couple’s children. Tedrow said the family decided to keep the property off the historic register in case the land would be worth more with the potential for demolition.

There is no publicly available list price because Tedrow offered a contract on the property before it hit the MLS.

She said the price of the existing house would depend on the exact configuration of a potential lot split, if approved, and other factors.

The house was featured as one of about a dozen properties in a 2004 book celebrating the architecture of Gamble Rogers in Winter Park by Patrick and Debra McClane.

“The initial series of interior spaces is unusual for a residence and more closely resembles a hotel or theater entry in that a lobby is provided, which is flanked by a coat room and a powder room,” reads the section on the property, referred to as the Plant House for its original owner. “Stepping up from the lobby, one then enters a large entrance hall nearly 45 feet in length. Triple arched openings on the south wall of the hall — with a fixed window in the center and double-leaf, multiplane doors on the sides — lead to the loggia and then the sunken patio, with Lake Osceola beyond.”

The house boasted features such as “floor buttons” in the dining areas that rang to wait staff in the kitchen, as well as “ornate wrought-iron railings and balusters [that] lined the staircase, and a velvet-covered handrail … provided on the interior wall.”

Jack Rogers, architect and son of Gamble Rogers, told the Voice last year that there are fewer than 10 true examples of his father’s work left in Winter Park as more are torn down every year.

“There’s probably 15 or 20 left, and eight or 10 are absolutely precious, and we seem to be losing them at the rate of one or two a year,” Rogers said. “We still have several wonderful examples.”

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