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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by Beth Kassab | Oct 7, 2026 | City Commission, Historic Preservation, Zoning and Development
New Merrywood Owner is Orlando Businessman Who Also Owns Corkcicle
In addition to the drinkware brand with local roots his interests also include a healthcare staffing firm that serves as a large government contractor
Oct. 7, 2026
By Beth Kassab
Editor’s note: This story has been updated to include comments from Steve Lockwood that were included in a press release from his attorney after the original story was published.
The person behind the limited liability company that purchased Merrywood, a lot on Palmer Avenue, is Steve Lockwood, an east Orlando resident who last year bought the Orlando-grown drinkware brand Corkcicle.
State corporate records also list him as a manager for a healthcare staffing firm that has been awarded $1.9 billion in government contracts, according to a federal database.
Lockwood is meeting with city officials and others in the community about splitting the lot in two ahead of a City Commission vote scheduled for next week.
After this report was first published on Wednesday morning, Lockwood issued a press release through his attorney Jason Searl of Maynard Nexsen.
“My intention when I purchased Merrywood was to create a home for my family, while also considering the possibility of splitting the property with a close family friend,” Lockwood said in the statement. “As I’ve learned more about Merrywood and what the property means to Winter Park, I’ve appreciated the opportunity to have constructive conversations with people who care deeply about its history and its future.”
Commission Elizabeth Ingram is one of the officials he has met with so far.
“It was hopeful that he was interested in hearing more about historic preservation and that there could be potential to save the home,” Ingram said. “I don’t feel we should approve the comp plan amendment without the city getting something back in return.”
Betsy Owens, executive director of Friends of Casa Feliz, said she met with Lockwood and would like to help him find “an elegant solution that allows him to build what he wants to build on the property” while also preserving Merrywood.
A demolition notice was posted at 1020 Palmer Ave. earlier this year.
“I think what that looks like is where the conversation will take place,” she said. “It was a good meeting.”
Lockwood does not live in Winter Park, and it’s not clear how he became interested in the nearly 4-acre property, which has recently been in the spotlight because it includes a nearly 90-year-old estate designed by James Gamble Rogers II. The home is listed on the Florida Master Site File, an inventory of historic and cultural assets kept by the Division of Historical Resources under the Florida Department of State.
He indicated in his statement that he would like to find a solution that preservationists are comfortable with.
“I bought Merrywood because I saw it as a special place where my family could build a home and become part of the community,” Lockwood said. “I also understand that the property means something to many people in Winter Park. I’m listening, keeping an open mind and hopeful that we can find a path forward that everyone can feel good about.”
Last month, city officials granted an extension on the permit to demolish the house while the property was being sold to Lake Osceola Holdings LLC, the entity that closed on the lot in August for $15 million.
Lockwood is seeking to continue the process of gaining approval to split the lot in two. That would require the City Commission to approve a special carve-out in the city’s long-term development plan, known as the comprehensive plan, which generally prohibits the splitting of lakefront lots. A split would increase the property’s value by allowing two lakefront homes instead of one.
“My client desires to continue with the pending Comp Plan Amendment and will accept responsibility for the application going forward,” Searl wrote to the city in September.
The second of two required commission votes to finalize the change to the comprehensive plan is scheduled for Oct. 14. The first vote on June 24 was 3-2 in favor of the lot split with Mayor Sheila DeCiccio and commissioners Kris Cruzada and Craig Russell voting yes and commissioners Warren Lindsey and Ingram voting no.
Lockwood’s LinkedIn profile lists him as the principal owner of Corkcicle and a graduate of the University of Central Florida. In state business records, he is listed as a manager or director for a number of companies, including Corkcicle Capital Group LLC, created in 2025, and Corkcicle Capital Group Holdings LLC, created earlier this year.
Cascadia Capital, an investment bank, announced last year that Corkcicle had been acquired by a private investor group. The company, which started in Orlando’s College Park neighborhood, sells stylish reusable water bottles and coffee thermoses, plus coolers, barware and more. Its website says it has collaborations featuring designs from Winter Park-based Rifle Paper Co., Disney and others.
Lockwood is also listed as a director or manager for Loyal Source Government Services and Loyal Source Worldwide. Orlando-based Loyal Source, founded in 2009, describes itself as a privately held healthcare, workforce, technology and mission-support company. In 2021, for example, the company provided “turnkey medical services to more than 20,000 Afghan evacuees at Camp Atterbury, Indiana and Fort McCoy, Wisconsin,” according to its website. The site also says the company provided care and services at a temporary shelter in Texas, under a government contract, to unaccompanied migrant children arriving at the U.S. border.
USAspending.gov, the federal database of government contracts created as a public access tool by the Federal Funding Accountability and Transparency Act of 2006, lists $1.9 billion in contracts to Loyal Source Government Services LLC since 2009. Most were awarded by the Department of Veterans Affairs, followed by the Department of Homeland Security, for services such as medical evaluations and screenings, nursing services and medical coding.
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by Beth Kassab | Sep 30, 2026 | Chain of Lakes, City Commission, News, Zoning and Development
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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by Beth Kassab | Sep 10, 2026 | City Commission, News, Zoning and Development
Plans for First Synagogue Roil Winter Park
The project, which also includes townhomes, drew 30 public speakers and failed to win enough support despite more concessions from Chabad
Sept. 10, 2026
By Beth Kassab
People affiliated with Chabad of Greater Orlando left City Hall disappointed on Wednesday night after final approval for what would be Winter Park’s first permanent synagogue was delayed until late October with commissioners saying they had too many concerns about parking, traffic and potential disruptions to those who live near the site in the heart of the bustling shopping and dining district.
Commissioner Elizabeth Ingram, who voted in favor of the project during the first hearing on the proposal on Aug. 26, said she was torn and having second thoughts after listening to more people and hearing concerns about construction related to the Rollins art museum nearby.
“We have residents who are concerned about this. And we have residents who are part of Chabad. And so I’m just trying to listen to both here,” Ingram said near the end of a more than two-and-a-half-hour discussion that drew 30 people who signed up to speak. “Going back to the current construction on the Rollins Art Museum, all of that traffic and parking impact is not being reflected in the traffic analysis right now … And I’m just hesitant now of whether this is the right time to approve this before we know what that traffic analysis would look like.”
As development debates in Winter Park so often go, the discussion featured a list of names recognizable for their careers or civic involvement and highlighted the city’s role as a home to people who wield influence across the region and beyond. Public meetings can sometimes take on an aura of a C-SPAN version of “Lifestyles of the Rich and — Locally — Famous.”
Much of the discussion centered on traffic worries from residents on or near Interlachen Avenue where homes and condominiums are valued at $2 million or far higher and where several churches already run preschools that contribute to congestion on top of the expansion of the Alfond Inn and museum construction.
Frank Santos, chief executive officer of Rosen Hotels & Resorts, lives next door to the proposed site and is concerned about parking as well as noise and disruption from a planned rooftop patio on top of the synagogue that will be rented for events and a playground for the daycare.
“I did send you all an email suggesting that you visit the site on a Saturday morning, which would be during the worship hours of the synagogue,” Santos told the commission. “I did that and sent you photographs and there was absolutely no parking in and around the area … I spoke to one merchant there, and they told me that parking beginning at 8 a.m. on a Saturday morning is non-existent with the Farmers’ Market.”
A rendering of what the proposed townhomes could look like.
Janet Robison, who lives near the Alfond Inn and said she has lived in her home on Lake Osceola for nearly 30 years, said she feared another big project in the neighborhood.
“I really enjoy living downtown,” she said. “Unfortunately, living there has been progressively more difficult, and people are always like, ‘Well, they can accept a little of this and all of that.’ But it’s adding up, all this accepting of things.”
But for some in the Commission Chambers, the logistical realities of development were outweighed by what they saw as a greater need — for Chabad to find a permanent home after it lost its Maitland building to a fire in 2024.
“Throughout this process, we’ve heard a sentiment that sounds reasonable on its face: We support a synagogue in Winter Park, just not at this location,” said Marni Stahlman, who attends the Chabad and is also chief executive of the Mental Health Association of Central Florida. “I ask you to think carefully about what those words mean in practice because there is a painful history behind telling Jewish people they’re welcome just somewhere else. This is not a hypothetical location. This is a property made possible through a donation that has been made available so that our congregation can finally a establish home.”
Ultimately, Ingram said she did not want to vote against the project and hoped that a resolution could come about to some of the concerns by the next vote. She joined Mayor Sheila DeCiccio and Commissioner Warren Lindsey, who both voted against the project previously, in a motion to table a decision until Oct. 28.
Commissioner Craig Russell also supported the delay after it became clear the development no longer had the votes to pass, but Russell said he preferred to go ahead and approve the project.
He expressed frustration at what he called “the cherry-picking and hole-poking of the engineer’s designs” when the commission can rely on city staff to vet projects and make sure they are built to code.
“The staff is going to keep them accountable, and they won’t get a [certificate of occupancy] if any of the stuff doesn’t work,” Russell said. “But none of us up here are architects or engineers.”
He also pointed to what he said was a critical fact that was being glossed over in the debate, which is that the new development will provide more parking than what exists currently for the El Cortez apartment buildings. The apartments would be razed at the corner of Morse Boulevard and Knowles Avenue just a block off Park Avenue to make way for the synagogue that includes a daycare and a rooftop patio for events and, separately, five townhomes.
Commissioner Kris Cruzada, the lone vote against tabling the matter, said he also wanted to see the project approved, noting the number of concessions Chabad made in order to satisfy concerns of neighbors and city officials. He said the Chabad proposal is less dense than a strictly residential proposal that could create up to 55 units on the lot.
“What they’re proposing is a drastic reduction in what could possibly be there,” Cruzada said. “… And here we have an applicant willing to bend over backwards to try and do this. They jumped through a lot of hoops to get here, you know, this is a difficult decision, and so in coming to a conclusion, I look at the conditions that they’re looking to go through, even to their potential detriment. The other churches don’t have caps to limit the number of kids that go there.”
Lindsey said he was struggling with the number of residents who argued for a need to limit new traffic and development.
“Everybody is in favor of the synagogue, and enthusiastically in favor of the synagogue,” he said. “And what we’re concerned about is pretty much every resident that lives in this neighborhood — I don’t know any of them that have not said this is going to create an incompatible and difficult traffic congestion problem that is going to be harmful to their enjoyment of their property. I mean, it’s been virtually unanimous.”
The El Cortez Apartments along Morse Boulevard.
Rabbi Dovid Dubov, who helps lead the Chabad, said the group agreed to even more conditions since the August vote such as limiting the days the rooftop patio can be rented to four per week and lowering the cap of children in the daycare from 60 to 50 as well as adding parking spots.
“Even since our last hearing, we have agreed to more, and I think the honest truth is that we have reached a point where we have extended ourselves as far as we reasonably can to make this work,” he said before the vote to table the proposal. “So, if everyone here supports a synagogue in our city, then I hope tonight we can turn that theoretical support into practical support. Theoretical support leaves us searching for a home, and practical support allows us to build one.”
DeCiccio suggested that more changes could occur to the proposal before the next vote at the end of October. She pointed to the site, which is 0.6 acres, and the amount of development the plans call for that would involve child pick-up and drop-off traffic for the daycare and catering trucks or other traffic for special events.
“No one can stand in that area and say it is not a mess now,” she said. “Plus, I am sure that the synagogue will be successful and is going to grow … For this proposal to work at this location, the developer and synagogue, I am feeling must scale back, perhaps by eliminating the townhomes or the rooftop venue or daycare. Or by limiting the project to just the synagogue alone. As proposed, the development is just too intensive for this site.”
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by Beth Kassab | Aug 26, 2026 | City Commission, News, Zoning and Development
Chabad Synagogue Approved in 3-2 Vote
The development will also include townhomes and a daycare that some neighbors said will cause too much traffic and parking problems
Aug. 26, 2026
By Beth Kassab
The City Commission on Wednesday approved a new development near Park Avenue to include a synagogue with a daycare and five townhomes after hearing from residents about the meaning of Chabad of Greater Orlando’s work and the importance of it becoming the first permanent synagogue in Winter Park.
The 3-2 vote followed more than three hours of discussions and comments, including objections from some neighbors who said they worried the project will create too much traffic, noise and parking problems. Commissioners Elizabeth Ingram, Craig Russell and Kris Cruzada voted in favor while Mayor Sheila DeCiccio and Commissioner Warren Lindsey dissented.
“I’m willing to risk parking and I’m willing to risk traffic so people and children can have a better understanding of each other,” Cruzada said just before the vote, adding, “I’m willing to live in a little discomfort” to show acceptance in the community.
DeCiccio and Lindsey supported a motion to postpone the vote, not because they oppose the synagogue, but because they wanted additional conditions on the project such as moving the location of three parking spots closer to the townhomes and an agreement that the synagogue would hold multiple simultaneous events.
“We would welcome a synagogue in Winter Park,” DeCiccio said. “We are with you. We stand with you. Attorney [Rebecca] Wilson can tell you we do this to everybody who comes in.”
Wilson of the Lowndes law firm represents the developer of the townhomes as well as the synagogue and has logged hundreds of hours in front of the Winter Park board over years answering questions about developments down to the smallest details from a commission known to publicly dissect proposals.
When the project passed on the first of two required votes, DeCiccio suggested that before the second vote next month the developer move three parking spaces closer to the townhomes on the 0.6-acre site at the corner of Morse Boulevard and Knowles Avenue where the El Cortez apartment buildings stand today.
The El Cortez Apartments along Morse Boulevard.
Other conditions previously approved by the Planning & Zoning Board include a requirement that child drop-off and pick-up related to the daycare take place in the underground parking area planned for the synagogue as well as prohibiting speakers or amplified music on the rooftop patio; requiring all noise and lights from the rooftop end by 10 p.m.; any expansion of the synagogue or daycare must go back to the city for approval and car lines related to daycare drop-off or pick-up can not spill onto the public streets.
Rabbi Dovid Dubov said most services at Chabad have just 10 to 30 attendees. He also said the location proved the best option for Chabad because other sites proved too expensive or not in a location that people could easily walk to. 
A rendering shows what the synagogue will look like from Knowles Avenue.
The 40-year-old organization lost its Maitland building to a fire in 2024 and has been operating out of a temporary space on the far end of North Park Avenue.
The proposal calls for 80 seats in the synagogue and the daycare is limited to 60 children. The five townhomes on the site are being developed separately and will be sold once completed.
Some residents who live in nearby townhomes and condominiums questioned the accuracy of a traffic study and noted how congested the small roads already become as a result of the Methodist Church preschool across Morse Boulevard and other church schools just blocks away.
Former Orange County Commissioner Ted Edwards attended the meeting on Wednesday and said he represented Frank Santos, who lives next to the site of the project and is chief executive officer of Rosen Hotels & Resorts.
Edwards said concerns centered on the Chabad’s planned rooftop event space that he said was more appropriate for a commercial area than a residential neighborhood.
People who attend the Chabad explained that Jewish law and tradition calls for some meals and events to be held outdoors, which is the reason for the patio.
Wilson pointed out that the Edyth Bush Charitable Foundation, a three-story building just one block down from the synagogue site and across Knowles Avenue, also rents out space for events without major disruptions to traffic or parking.
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by Beth Kassab | Aug 19, 2026 | City Commission, Historic Preservation, Zoning and Development
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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