Commission Delays Merrywood Vote as Preservation Talks Continue

by Beth Kassab | Oct 15, 2026 | Chain of Lakes, City Commission, Historic Preservation, News, Zoning and Development

Commission Delays Merrywood Vote as Preservation Talks Continue

Matt Morgan is still trying to buy the property as Commissioner Kris Cruzada pushes for compromise for ‘conscience’ of city

Oct. 15, 2026

By Beth Kassab

The fate of Merrywood remained uncertain the morning after a more than four-hour meeting devoted to determining how much, if any, of the historic property must be preserved for its new owner to get permission from the City Commission to split the lakefront lot he purchased in August for $15 million into two.

As these debates often do in Winter Park, the discussion touched on more than the fate of one house. For many, it reflected a collective angst over losing the architectural diversity and history that, along with its walkability and lush tree canopy, have long earned the city acclaim as a destination for visitors and people seeking a Florida lifestyle in a New England-style village.

Natalie Brethauer, one of at least 10 people who signed up to speak at the meeting, illustrated that tension between old and new. She told commissioners she grew up in Winter Park, moved away for college and lived in other vibrant cities, including Denver, Houston and the Old Town neighborhood of Alexandria, Va., before returning home and marrying at the Capen House, which had been slated for demolition before it was floated across Lake Osceola to be preserved.

“The whole reason I came back to Winter Park is because it is such a unique and beautiful place to raise a family and live,” she told commissioners. “And something that I’ve noticed since moving back, and it’s really ramped up post-COVID … It looks as though it’s like a dystopian-type vibe happening here. You go down Palmer [Avenue], and to me, I describe it as like an evil villain lair in ‘The Incredibles’ movie or something. Like, what are these homes that are being built? I thought the whole point of Winter Park was its beautiful historical charm, and that was the lure and the draw, and so it’s just really sad to see a lot of that going away.”

She was referring to the proliferation of what have become known as “white box” houses. Though they aren’t always white, the homes feature sharp edges and an ultra-modern aesthetic more common in, say, Miami Beach than along the local brick streets fronting the Chain of Lakes.

After the meeting, Commissioner Kris Cruzada, who voted in June along with Mayor Sheila DeCiccio and Craig Russell to approve a lot split without any preservation conditions, said he considered Brethauer’s comments representative of part of the “conscience” of Winter Park. He said that sentiment was one reason he pushed so hard Wednesday night for a compromise that would preserve some portion of Merrywood in exchange for allowing the lot split.

Attorney Jason Searl, who represents Steve Lockwood, points to areas on the Merrywood facade that could potentially be saved.

The property at 1020 Palmer Ave. has already set a record for the highest sale price in Winter Park at $15 million. It would become even more valuable if it were subdivided so that a portion could be sold separately.

Lockwood said during the meeting that a close family friend wanted to purchase the new lot and build a house there. Lockwood, who sat through the hours-long meeting with his wife and daughter, said he plans to build a new house for his family behind Merrywood. The existing house would be at least partially demolished and converted into what he called a “guest house.”

After the meeting, Lockwood told the Voice he would hire an architect and try to determine what would be feasible under a condition proposed by Cruzada that would require preserving a portion of the nearly 90-year-old estate. The house was designed by James Gamble Rogers II and is listed in Florida’s database of historic and cultural assets.

Cruzada’s shift in position was key to the commission’s unanimous 5-0 vote to delay a decision until Nov. 11, giving new owner Steve Lockwood time to outline what portion of the house he believes could be preserved.

Commissioners discussed retaining only a portion of the facade, or front wall, while gutting everything else.

New Merrywood owner Steve Lockwood speaks at the City Commission meeting on Wednesday.

“Just like a billboard?” asked Commissioner Craig Russell, conjuring the image of an old Hollywood set piece.

Even after the meeting was recessed to give the owner and his lawyer time to try to work out some terms, it remained unclear how much of the house would need to be preserved to secure at least three votes on the commission, or how much Lockwood considered feasible and affordable.

Throughout the meeting, Lockwood and his attorney, Jason Searl of Maynard Nexsen, pointed to inspection and engineering reports that appeared to have been prepared earlier this year, when Tara Tedrow was still under contract to buy the property. The reports indicated that the house was in a state of disrepair beyond saving.

Searl showed commissioners an overhead projection of the house and pointed to a section of the facade, perhaps 30 feet long, that he said could potentially be restored.

That led to an exchange among commissioners that got to the heart of the discussion.

Commissioner Elizabeth Ingram said 30 feet was inadequate.

“That’s not the architecture,” she said. ” That’s not the beauty of the home. It’s not the house anymore. To me, if you were willing to keep that entire facade, that front whole section where you have the extra height on this side, and then you have the little rounded space around the side. That is the coolness. That is the charm and the beauty and the style of James Gamble Rogers.”

Ingram also said preserving so little would “erode” the city’s comprehensive plan, which must be amended to allow the lakefront lot to be split. The plan generally prohibits lakefront lot splits.

“That doesn’t encourage one bit of historic preservation, which we all claim to love and respect and want to promote, but then we’re going to be OK with just keeping 30 feet of this ginormous, beautiful home? Like, what are we doing?”

Cruzada argued that preserving some of the house was better than preserving none of it.

“I guess what I’m trying to do is find a path to some level of preservation or we lose it all together,” Cruzada said. “You know, we’re in an unfortunate set of circumstances. He’s here before us trying to compromise.”

“No, he’s here trying to have us compromise our comp plan,” Ingram replied.

“You’re right,” Cruzada said. “But the other side is if we don’t allow the lot split, then he’s still going to go forward with the demolition permit. Then we don’t have anything.”

Lockwood, who owns federal government medical staffing contractor Loyal Source and last year purchased the Orlando-based drinkware brand Corkcicle, and his attorney opened the meeting by saying they were unwilling to put any preservation conditions in writing beyond a commitment that Lockwood would make a “good faith” effort to preserve a portion of the house.

Searl proposed allowing any square footage Lockwood preserved to count toward the potential additional square footage of the new homes on the divided lot. The commission has sought to limit the combined size of the homes to 30,000 square feet.

Searl said that if commissioners did not approve the lot split Wednesday, Lockwood would move forward with demolishing the house and potentially seek approval for the lot split in the future. He quoted former owner Cathy Gilmer, who spoke during the June meeting and called the house “basically a waste” that falls further into disrepair every day it remains standing.

Searl said Lockwood was discouraged and offended by an open letter to the City Commission, organized by the Friends of Casa Feliz and signed by nearly 300 people, that called on the city to deny the lot split unless Lockwood agreed to designate the house as historic.

The letter came as a disappointment and a surprise, Searl said, after Lockwood spent two hours meeting with the leaders of Casa Feliz, another Gamble Rogers-designed house that was saved 25 years ago when it was moved across Interlachen Avenue to its current location on the Winter Park Nine. It now serves as a museum and popular event venue.

“When that happened, it feels like to us you’re then fighting a losing battle, and anything you say will not achieve a cooperative spirit from that group,” Searl said.

When it was Betsy Owens’ turn to speak, she explained that Lockwood knew about the letter and called for at least 80% of the house to be preserved, including the entire front elevation.

“When Mr. Lockwood and I met last week, I mentioned this letter,” said Owens, executive director of Friends of Casa Feliz. “It’s been in circulation for about two months, so this was not at all a reaction to that meeting. We were very upfront about that. We recognize an uncomfortable reality: Merrywood is not historically designated and could be legally demolished tomorrow, but today the city has something it ordinarily lacks, and that is leverage. The owner is asking you to change the comprehensive plan. That gives you an opportunity to secure preservation protections in return … We understand that saving some portion is better than losing all of it. We don’t want the perfect to be the enemy of the good.”

Lockwood later apologized for misunderstanding the open letter, saying he thought it was a new letter rather than the one Owens had already told him about.

After initially insisting he would not agree to delay the vote and would rather face a rejection than push the hearing to another meeting, Lockwood ultimately agreed to wait until November.

Matt Morgan, center, listens to the debate over Merrywood during the Winter Park City Commission meeting.

That leaves four weeks for a potential compromise to take shape or another twist to emerge in the saga of Merrywood.

Matt Morgan, one of the faces of the Morgan & Morgan law firm who lives in a historic home in Winter Park not far from Merrywood, sat in the commission chambers for nearly the entire meeting but did not speak.

On Thursday morning, he sent a letter to commissioners reiterating his desire to purchase the property. Morgan emerged publicly as a potential buyer over the summer after commissioners were told during the first vote that Merrywood had to be demolished because no one was willing to invest the money needed to restore it.

“I want to make certain the commission understands that I am willing to assume the financial responsibility and substantial undertaking necessary to preserve and restore the home,” Morgan wrote on Thursday morning. “I recently offered to purchase Merrywood for its pro rata share of the $12 million contract price. I also indicated that, upon reviewing the operating agreement for Lake Osceola Holdings, I would be willing to increase that offer.”

Tedrow reportedly had the property under contract for $12 million contingent on the lot split going through. Lockwood purchased the property under Lake Osceola Holdings LLC for $15 million, though his identity wasn’t known until last week and it’s unclear why the price went up by $3 million.

Morgan said Searl has told him the property is not for sale.

But Morgan said he remained hopeful the house would be preserved and expressed relief that the second and final vote on the lot split was delayed.

“Thank God they took a breath,” he said. “Because they were getting ready to entirely change the code on a hope and a prayer.”

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