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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by Beth Kassab | Aug 5, 2026 | City Commission, News, Zoning and Development
Synagogue, Daycare and Townhomes Win Approval from Planning Board
A number of residents spoke for and against the project that will result in the first permanent synagogue in Winter Park
Aug. 5, 2026
By Beth Kassab
After more than 20 residents spoke out during a two-and-a-half hour discussion, Winter Park’s first permanent synagogue won unanimous approval on Tuesday evening from the Planning & Zoning Board.
While some who addressed the board expressed concerns about traffic related to a daycare that will be run by Chabad of Greater Orlando and also noise or other neighborhood disruptions from a rooftop patio proposed for the top of the building, the board members said most of their questions about the development were answered.
The P& Z board added one condition to its approval the development, which also includes five townhomes at the 0.6-acre site at the corner of Morse Boulevard and Knowles Avenue where the El Cortez apartment buildings stand today.
Board members voted 5-0 to adopt the conditions recommended by staff and add a requirement that child drop-off and pick-up related to the daycare take place in the underground parking area planned for the synagogue.(Chairman Jason Johnson and members Bill Segal, Vashon Sarkisian, Samuel King and Charles Steinberg were in favor. Member Alex Stringfellow, who works as an urban planner and was asked to consult on the project before the application was made, recused himself from the vote and member Michael Dick was absent) The other conditions include 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.
A more modern design for the new Chabad of Greater Orlando was favored by the Planning & Zoning Board.
“It’s clear that this property could be developed at a higher capacity, which is going to bring up a whole lot of issues regarding parking and traffic,” said member Vashon Sarkisian, an urban designer. “So I think we have to consider that this is, you know, a coveted area and that there’s going to be redevelopment … so what is the right use? Well, I am in favor of this use. I think it’s, like so many people said, it’s something that’s missing in the city of Winter Park.”
Earlier in the evening, Jewish residents spoke about their desire to have a synagogue closer to their homes and the positive impact of Chabad on their lives.
“Chabad has been a part of my life for a long time. It’s where my parents met. It’s where I celebrated my Bar Mitzvah, and it’s where I’ve celebrated all my holidays,” said Daniel Isaak, 16. “… It’s about allowing a community to worship where it already lives. You know, all of my Christian friends, they all have churches in their own city, and they can practice their faith close to home surrounded by their neighbors. So why should Jewish families have to leave their own community to do the same?”
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.
Several people who attend Chabad said only 12 to 15 people typically are at Friday evening services.
The proposal, which still must be approved by the City Commission, is capped at 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.
Rabbi Dovid Dubov said many people who will attend services or use the daycare will walk rather than drive, which will help alleviate traffic concerns. Jewish law prohibits driving on Shabbat, for example.
“Our responsibility is to make Jewish education available where Jewish families live,” Dubov told the board. “And today, ladies and gentlemen, there is no Jewish daycare in Winter Park. We have also worked diligently to be respectful of our neighbors. We voluntarily limited our daycare to just 60 children, approximately one-fifth the size of nearby church schools, and our traffic study demonstrates that that impact will be extremely minimal.”
But some residents who live in nearby townhomes and condominiums questioned the accuracy of the 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.
Frank Santos, who lives next door, said the area is already undergoing enormous change and contending with traffic and parking problems. Santos, chief executive officer of Rosen Hotels & Resorts, which has a long history of supporting local Jewish causes led by its late founder Harris Rosen, said his own rooftop living space will be impacted by as many as 80 people using the synagogue’s rooftop deck because of the proximity.
“Chabad of Greater Orlando and it’s member should have a synagogue in Winter Park,” Santos said. “Knowles Avenue is not the right location. Find a site with less density and appropriate parking.”
Marc Hagle, who is known for constructing the largest private residence in Winter Park at 40,000-square-feet on Palmer Avenue and for taking two Blue Origin suborbital space flights in recent years, said he attended the meeting with the intention of speaking against the project, but was impressed by the presentation. Still, he noted potential traffic congestion and also questioned if redeveloping the site mostly as a synagogue would have a negative tax impact to the city because religious institutions are generally exempt from paying property taxes.
“I think the tax implications to the city are a problem,” Hagle said. “The city is facing some really interesting tax problems coming up with the laws that are changing,” he noted, an apparent reference to the amendment on the November ballot that could significantly decrease property taxes collected by local governments.
The El Cortez Apartments along Morse Boulevard.
“By putting something in the area that’s tax exempt, I think you’re creating a potential problem for the future,” he said. “We’re all interested in making sure that the city meets its obligations and it maintains standards that, quite frankly, the city hasn’t done for the past five to ten years. This isn’t the right place to say this, but the quality in the city isn’t what it used to be.”
Several longtime Winter Park residents who are Jewish noted the meaning of the synagogue after a history of discrimination against Jews across the country, including in Winter Park.
“It has been a problem being Jewish in Winter Park, to be candid,” said Barry Render, a former longtime Rollins College professor. “When I moved into my house on Via Tuscany and applied for membership in the Racket Club, which is just a block away from me, I was turned down because I was Jewish.”
He also noted that the holiday celebration in Central Park did not always include a Hanukkah menorah as it does today.
David Jasmund, who lives close to the site on Interlachen Avenue, was one of several people who attended the meeting who said they were “disappointed” that any of the concerns about the development were being linked to bigotry.
“That’s disappointing,” he said. “Unfortunately, it’s around us today in society, which I think is really depressing at times.”
Jasmund said he didn’t have any concerns related to the synagogue itself, but questioned the capacity of the roads to handle another daycare in such close proximity to others.
“I think it’s unrealistic to think that someone is going to drive a 1-year-old or a 2-year-old down into a basement … take them out of a car seat, take them upstairs, and get 60 people in and out of there without it being stacked up on Morse, Interlochen, Knowles, and maybe even Park Avenue.”
Hattie Wolfe, another speaker who lives nearby, said parking in the area is already “impossible.”
A rendering shows what the townhomes on the site will look like.
“I’m Jewish,” she said. “I have nothing against the synagogue, but I don’t think it’s the right place for it, judging by what’s happening to the town.”
Becky Wilson, the Lowndes law firm attorney who is representing the synagogue and often represents development projects in Winter Park, said the project is doing everything possible to address concerns about traffic, parking and density.
“I think what occurred to me and that I’ve grown to appreciate while working on this project is how important having a synagogue in the city of Winter Park is to the Jewish residents,” she said. “And, in particular, to have one downtown where many of the other large, important churches are also located. What I’d also say to those residents is I’ve stood here for over 20 years, and I’ve never brought a project forward where I didn’t have to answer questions about traffic, parking and density.”
P&Z Chairman Jason Johnson asked Wilson if Chabad would agree to the condition that daycare pick-up and drop-off must occur in the underground garage to help with traffic flow and she said the group would agree. He suggested parking on the site is likely a “net benefit” for the downtown area once El Cortez is gone because people utilize street parking related to the apartments.
“There are people I deeply respect on both sides of the issue who have made their their comments to the board tonight,” Johnson said. “… My main concern with the traffic was not the number of trips, but rather the flow of traffic through the site for day care drop-off and pick-up. I think if that traffic flow can be directed directly into the garage below the facility, it would help alleviate that quite a bit.”
The next step for the project is a hearing in front of the City Commission.
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