New Merrywood Owner (Who is Still Unknown) Will Pursue Lot Split

A second vote on the property that is known as the site of a large James Gamble Rogers II estate is scheduled for Oct. 14

Sept. 30, 2026

By Beth Kassab

One of Winter Park’s most closely guarded secrets — the identity of the new owner of the lot known as Merrywood at 1020 Palmer Ave. — may soon be revealed.

Jason Searl, a real estate attorney at Maynard Nexsen, sent a letter to Winter Park Planning Director Allison McGillis on Sept. 23 saying he was recently hired to represent Lake Osceola Holdings LLC, the entity that closed on the nearly 4-acre property in August for $15 million, and that the new owner is seeking to complete the process needed to split the lot in two.

“My client desires to continue with the pending Comp Plan Amendment and will accept responsibility for the application going forward,” Searl wrote.

The second of two required City Commission votes to finalize the change to the city’s development plan, which would carve out a special exception to Winter Park’s prohibition against lakefront lot splits for Merrywood, is scheduled for Oct. 14.

McGillis told the Voice she does not know who is behind Lake Osceola Holdings LLC, but said Searl indicated to her in a conversation that the new owners would likely meet with commissioners or potentially appear at the public meeting. That could mean they would be identified and potentially discuss their plans for the property.

She said she does not have any details about the owner’s plans, but said she was told it was possible that some portion of the 90-year-old estate on Lake Osceola could be preserved. The house is listed in Florida’s master file of historic resources and is among the last remaining examples of the local influence of architect James Gamble Rogers II, and is known as one of his largest and most ornate works.

Tara Tedrow, the Lowndes attorney who originally had the property under contract and began the lot split process last year, was copied on the email thread that included Searl’s letter and followed up with her own note indicating that she would no longer be involved in the process.

“Please accept this email as written confirmation of a transfer of my pending comp plan application to Lake Osceola Holdings, LLC,” Tedrow wrote.

McGillis requested the correspondence from both Tedrow and Searl so that she could meet the deadlines for public notice ahead of the Oct. 14 scheduled vote.

Neither Searl nor Tedrow responded to requests for comment from the Voice on Wednesday.

Lake Osceola Holdings LLC filed its articles of incorporation with the state of Florida’s Division of Corporations on June 10. It listed Carla Deloach as the manager of the company, and its Orlando address is the same as Cypress Row Advisors, where Deloach is a senior attorney.

On that same date, Tedrow filed with the state a company called Ketara RE LLC and listed herself and her husband, Kevin Skorman, as the managers.

June 10 fell about a week after the Planning & Zoning Board recommended that the City Commission approve the lot split, and about two weeks before the first hearing related to the property in front of the City Commission.

Tedrow did not respond to questions about whether the company she registered on June 10 was related to the lot on Palmer Avenue. She is also listed as a manager, along with Skorman, a local commercial and residential developer, on three other companies filed with the state between March and September.

Tedrow told city officials throughout the process that she hoped to build a home for her family on the empty portion of the Merrywood lot, which is not far from the house she grew up in, and sell the other portion.

She told the City Commission that she and Sotheby’s agent Mick Night hoped to find a buyer willing to preserve and restore Merrywood, which is now in disrepair, but that no one came forward after nearly a year of searching.

That led Mayor Sheila DeCiccio to say that there was little choice but to approve the lot split, because the house was likely to be demolished either way, and Tedrow said she would walk away from the deal if the split wasn’t approved. DeCiccio said she feared that without the split, another buyer would come along and build a house as large as 50,000 square feet, based on the entitlements related to the size of the lot. As a result, the City Commission voted 3-2 on June 24 in the first of two required votes to approve the split.

Not long after that, the Voice first reported that Matt Morgan, a Winter Park resident and key face of the Morgan & Morgan law firm, made an offer on the property in August 2025 for $10 million. Night said the offer was too low and that, at the time, he was unaware of Morgan’s desire to preserve the home.

Morgan, who currently lives in a home on the city’s historic register, then upped his offer to $12 million and said he would like to see Merrywood preserved.

The city extended a demolition permit for the property in August. City officials have little power to require the home be preserved because its longtime owners, before the most recent sale, never listed it on the local register.

The clearest path to keep the home standing is for the City Commission to approve the lot split with a condition that the home remain in place and be listed on the register — similar to a condition placed on a different property in recent years, in a case where the owner was also seeking to split the lot.

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