Merrywood Sold for $15 Million to New Buyer

A city official says the request for a lot split will likely be tabled instead of heard at next week’s City Commission meeting

Aug. 19, 2026

By Beth Kassab

The historic home known as Merrywood was sold this week for $15 million to a company called Lake Osceola Holdings LLC, which is tied to an Orlando attorney and an estate advising firm called Cypress Row Advisors.

A deed dated Aug. 18 was filed with the Orange County Comptroller’s Office naming Raymond and Cathleen Gilmer as the sellers and the new company that was just created in June as the buyer for $15 million.

Winter Park Planning Director Allison McGillis said she spoke with Tara Tedrow, who previously had the property under contract for a reported $12 million and was requesting a lot split, and said she now expects Tedrow to ask for the lot split discussion to be tabled. The discussion had been scheduled for next week’s City Commission meeting.

Winter Park’s land development rules generally prohibit subdividing lakefront lots. Tedrow was seeking special permission through a change to the city’s comprehensive plan that governs development.

That prompted an outcry from historic preservationists who wanted to save the 90-year-old estate that is among the last remaining examples of the influence architect James Gamble Rogers II left on Winter Park.

The buyer, Lake Osceola Holdings LLC, filed notice of the new company with the state of Florida on June 10, according to state records. That was a week after the Planning & Zoning Board recommended that the City Commission approve the lot split and about two weeks before the first hearing regarding the house in front of the City Commission.

Carla Deloach is listed as the manager of the company and it’s Orlando address is the same as Cypress Row Advisors where Deloach is a senior attorney.

The sales deed was prepared by Jason Williams of the Lowndes law firm, where Tedrow is also a shareholder.

Tedrow began seeking the lot split last year, which she has said would allow her to build a family home on the vacant portion of the nearly 4-acre property and sell the other portion with the Merrywood house. Undeveloped lakefront lots are scarce in Winter Park.

Tedrow said at multiple public meetings that she hoped to find a buyer to preserve Merrywood, but said the house was in a state of severe disrepair.

Tedrow and Mick Night, the Sotheby’s real estate agent handling the transaction, said no one had come forward to preserve the home despite months of marketing the property because it was in such rough shape. As a result, they said at the June 24 City Commission meeting, there was little choice but to demolish the property.

Tedrow said her contract was contingent on the city approving the lot split.

The City Commission voted 3-2 that night to change the comprehensive plan to allow for a split that would only apply to the home at 1020 Palmer Ave. but added conditions: the combined total of two new homes that could be built on the lots would not exceed 30,000 square feet and at least one be fashioned in a style adjacent to architect James Gamble Rogers II, the local architect who built Merrywood and is known for helping to shape the city’s aesthetic character.

Attorney Matt Morgan, who also lives in Winter Park, then came forward with a $10 million offer, later upped to $12 million, to preserve the home. But he never heard a response from the sellers.

“I don’t know what to think because nobody knows what the intention or the plan is,” Morgan told the Voice on Wednesday morning after hearing word of the sale. “I think it’s a wait and see thing.”

McGillis said she doesn’t know who the buyer is, but that she heard from Tedrow that it’s a couple who emerged after the first hearing related to the lot split request.

“What she told me is that [the new buyers] are comfortable enough to close on the property without any guarantee,” of a lot split, McGillis said, adding that she understood all options are likely on the table from preserving the house to demolishing it. 

While a permit is already in place would allow for the home to be bulldozed any day now, the owners and Tedrow verbally agreed to hold off on demolition until the second reading of the comprehensive plan change — which had been scheduled for next week and now is likely to be delayed or even cancelled all together.

Tedrow said she facilitated the demolition permit in an effort to bring the conversation about the house in front of the Historic Preservation Board. The 1938 Merrywood property is listed  the Florida Master Site File, which means the demolition permit received a 90-day hold. The current permit is good through the end of August.

The home is not on the city’s historic register, leaving city officials without any power to stop demolition. McGillis recommended that a historic designation be one of the conditions of the lot split approval — a condition the city has required and approved before — but the commission rejected that after they heard no one was willing to preserve the home.

Betsy Owens, executive director of preservation group Friends of Casa Feliz, said the group would still like to see the home maintained.

“Until the house comes down we remain hopeful that a preservation option exists,” she said. “It would be a terrible loss if the house were demolished given that there is a known vetted buyer in Matt Morgan, who was willing to preserve the house.”

For now, the future of the estate remains in limbo.

“The saga is to be continued,” Morgan said.

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