by Beth Kassab | Nov 11, 2026 | Chain of Lakes, City Commission, Historic Preservation, News, Zoning and Development
Most of Merrywood Saved After Facing Months of Likely Demolition
Commissioners, preservationists and the new homeowners celebrated a 4-1 vote that keeps most of the historic James Gamble Rogers II estate standing
Nov. 11, 2026
By Beth Kassab
After nearly a year of uncertainty and expected doom, preservationists, city officials and Merrywood owners Steve and Jenny Lockwood were jubilant Wednesday afternoon after commissioners voted in favor of a deal to save the 90-year-old historic estate from the bulldozers.
Steve Lockwood and Betsy Owens, executive director of Friends of Casa Feliz, briefly embraced and shook hands after the 4-1 vote finalized an agreement that marked a significant change of heart from just a month earlier, when Lockwood resisted making a written commitment to preserve the house.
One key difference in the conditions governing the special approval to split the 3.67-acre lot on Lake Osceola is that houses on both lots may be up to 15,000 square feet, plus accessory structures. The square footage of the home preserved on the Merrywood lot will not count toward that limit.
“Remember, I stood up here on [Oct.] 14 and said nothing in writing, nothing recorded, right? And we moved off of that,” said Jason Searl, Lockwood’s attorney with the Maynard Nexsen law firm. “… We are asking for this and, in return, the city is going to get the preservation.”
A major factor in moving the deal forward, Owens said, was the vision of architect Michael Wenrich, who serves on Casa Feliz’s board. Wenrich worked with the Lockwoods to help them reimagine the property in a way that preserves most of the estate while also meeting their needs for a family home.
Lockwood plans to build a new primary suite and three-car garage while demolishing the original maid’s quarters, an enclosed sunroom and an upstairs sitting room.
Searl said Lockwood’s friend and business partner plans to purchase the second lot created next to 1020 Palmer Ave. and build a home there.
Owens spoke in favor of the agreement, which will preserve about 6,200 square feet of the existing 7,300-square-foot house. A covenant will run with the land, meaning future owners will also be required to uphold the agreement.
“I know the road ahead will bring challenges and surprises, but having come to know Jenny and Steve over the past six weeks, I’m confident that they’re equal to the task,” she said. “Twenty-five years ago, the community came together to save Casa Feliz. Today, we have an opportunity to write another chapter in Winter Park’s preservation story.”
Commissioner Warren Lindsey noted how far the Merrywood saga had come since the first prospective buyer obtained a demolition permit in February and appeared poised to tear down the house. At the time, he said, there seemed to be no hope of saving it and no buyer willing to try.
“There was discussion that it was this futile situation, that Merrywood could not be saved, that it was in terrible condition, etc.,” Lindsey said. “So it can be saved, right?”
Searl said yes. The Lockwoods, who purchased the property in August for $15 million, have only recently begun developing specific plans for it. They now believe there is a way to repurpose the home, which has been vacant for about a year following the deaths of its previous longtime owners.
As a result of the agreement, Lindsey said he would also reverse his earlier position, changing from a no vote during the first hearing over the summer to a yes vote Wednesday night. He said his primary concern — setting a precedent for future lakefront lot splits — had been addressed by the agreement, which requires much of the existing home to be preserved rather than allowing the property to become two blank-slate lots.
“I just want to emphasize that the reason why I’m 180 degrees changing from a no vote to a yes vote is because I think the Lockwoods, by their noble agreements, have substantially complied with the comprehensive code that allows a lakefront lot split under certain circumstances, and the reason why I bring this up is because there are lots and lots of large lakefront lots in Winter Park,” Lindsey said.
Commissioner Elizabeth Ingram cast the lone no vote. She said she voted against the agreement because it was clear it would pass, and she wanted to send a stronger message about the need for an official historic designation, which the agreement does not provide.
“I can see that it’ll pass, and I am also very grateful for how this has turned out,” she said. “I think I knew from the very beginning when this all started that it was definitely worth saving, but I am concerned about the precedent that we are setting, that we’re going to have lots of lakefront property owners coming and asking for their sweetheart, specifically written amendment.”
After the meeting, Lockwood said he was pleased with the approval and hoped to preserve some of the home’s interior details, including its tile and woodwork characteristic of James Gamble Rogers II. He emphasized, however, that the planning process is still in its early stages.
Owens noted that the agreement “won’t freeze the house in time,” but will “save the lion’s share of this architectural treasure, its essential design, its historic facade and public presence, and its place among the landmark homes that give Winter Park its distinctive character, sense of place, and enduring property values.”
She said the story of Merrywood is also the story of “local democracy working exactly as it should.”
“Our commissioners have been accessible, responsive, and willing to listen,” she said. “They’ve known when to press the pause button and ask hard questions and seek more information. They’ve heard from citizens on all sides. Our local media has kept the broader community informed, enabling people who can’t attend a 3:30 weekday meeting to participate in the process, and city staff has worked tirelessly from the beginning to find common ground, recognizing that Winter Park’s increasingly rare historic homes are worth fighting for.”
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by Beth Kassab | Nov 10, 2026 | Arts and Culture, Chain of Lakes, City Commission, Historic Preservation, Zoning and Development
New Plan to Save Most of Historic Merrywood Advances Toward Final Vote
The new terms represent a significant turnabout from just months ago when it appeared the property would be demolished
Nov. 10, 2026
By Beth Kassab
Merrywood may be saved after all — or at least most of it.
An agreement that would preserve at least 80% of the historic lakefront estate’s square footage, along with 70% of the linear footage of its front facade, will be up for approval by the City Commission on Wednesday afternoon.
If approved, the general terms of the amendment to the city’s comprehensive plan would allow the nearly 4-acre lot at 1020 Palmer Avenue to be split in two while adding a deed restriction that runs with the land. The restriction would prohibit the demolition of most of the house and require any additions to be architecturally consistent with “a Mediterranean, Mission, or James Gamble Rogers II influence.”
The deal represents a significant turnabout from just months ago, when the property appeared headed for certain demolition after the previous owners and an earlier prospective buyer said there was no hope of saving it. Last month, the commission delayed the second and final required vote until this month after questions remained about exactly how much of the house would be preserved in exchange for the lot split. The split would be a lucrative benefit for any owner because it would allow a portion of the land to be sold for new construction.
New owner Steve Lockwood, who paid $15 million for the property in August, now appears to be considering Merrywood as a primary residence rather than a “guest house,” as he previously proposed.
Lockwood did not respond to a phone call or text message. Jason Searl, his attorney, also did not respond to a request for comment.
Betsy Owens, executive director of Friends of Casa Feliz, said she was optimistic about the new terms being proposed.
Her group has worked to save the house, which it views as one of the largest and most significant remaining examples of the work of local architect James Gamble Rogers II and a critical piece of the city’s history as told through architecture and design.
“The most significant parts of the house would be preserved, and the front facade is largely being preserved, so it does feel like this is tantamount to preserving the home,” Owens said.
She said some features of the house would be nearly impossible to replicate. She also noted the intrinsic value of owning a piece of Winter Park history that is visible not only from Palmer Avenue but also by boat from Lake Osceola.
A view of the front entrance to the home.
City Planning Director Allison McGillis said the proposed terms would allow the demolition of a sunroom toward the back of the house that was added later, as well as the original maid’s quarters. The other portions would be preserved.
The deal, much like an actual designation on the city’s historic register, would not prohibit the owner from making changes to the interior of the house. The entire layout, for example, could be reimagined, with modern amenities such as a larger kitchen and additional closet space. It’s possible, though, that some aesthetic features, such as tilework or woodwork, could be preserved or reused.
The house, known as Merrywood, is not on the city’s historic register because the longtime owners, who are now deceased, chose not to list it. As a result, it could have been demolished with a simple demolition permit, which became active earlier this year.
However, the property is listed on the Florida Master Site File, a state database of historical and cultural resources. That listing means the city’s Historic Preservation Board could delay a demolition request for 90 days to allow time to consider alternatives or ways to preserve portions of the home.
That process opened the door to public discussions about the house and whether the City Commission should approve the special request to split the 3.67-acre lot without receiving something in return from the property owner — namely, a guarantee that at least some of the home’s historic character would remain standing. Lot splits on lakefront properties are generally prohibited in Winter Park.
The house was featured as one of about a dozen properties in a 2004 book by Patrick and Debra McClane celebrating Gamble Rogers’ architecture in Winter Park.
“The initial series of interior spaces is unusual for a residence and more closely resembles a hotel or theater entry in that a lobby is provided, which is flanked by a coat room and a powder room,” reads the section about the property, which was referred to as the Plant House after its original owner. “Stepping up from the lobby, one then enters a large entrance hall nearly 45 feet in length. Triple arched openings on the south wall of the hall — with a fixed window in the center and double-leaf, multiplane doors on the sides — lead to the loggia and then the sunken patio, with Lake Osceola beyond.”
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by Beth Kassab | Oct 29, 2026 | City Commission, Historic Preservation, News, Zoning and Development
Commission Approves New Office Development in Hannibal Square
The board, in response to comments from residents, said a committee will determine ways to honor the neighborhood’s heritage
Oct. 29, 2026
By Beth Kassab
The City Commission on Wednesday unanimously approved a plan to replace the now-demolished Gardens at DePugh, a 40-bed nursing facility that closed last year, with 10 office buildings. The facility was historically significant for its roots in serving Black families during segregation.
Commissioners said they would form a committee that includes developer Zane Williams and residents Maria and Martha Bryant, who spoke at Wednesday’s meeting, to explore additional ways to honor the history of Winter Park’s historically Black Hannibal Square neighborhood as redevelopment continues to reshape the area.
Martha Bryant, a longtime resident, said much of the west side’s legacy has been “destroyed.”
A plaque that honors the former Gardens at DePugh nursing facility still stands at the corner of Morse Boulevard and Pennsylvania Avenue.
“You look around and you don’t see where are the Black people who have worked to build Winter Park? Where are the homes? They have been removed, just like the Mary DePugh Nursing Home has been removed,” Bryant said. “At least her name, a monument or something, should be there.”
She suggested that a portion of the tax revenue or other funds generated by the new development could be directed to the Hannibal Square Heritage Center, a museum dedicated to the neighborhood that is operated by Crealdé School of Art.
Commissioner Craig Russell, who will also serve on the committee, suggested renaming a portion of Welbourne Avenue in DePugh’s honor.
Commissioner Kris Cruzada also proposed a condition of approval, which the other commissioners supported, requiring that a plaque honoring DePugh be moved from the corner of Morse Boulevard and Pennsylvania Avenue to a more prominent location in front of the new development. The plaque could be accompanied by landscaping and a bench.
The goal, Cruzada said, was to create a place that could “really invite somebody to read it and look at it and stay a while and think about it.”
The city will also determine the cost of adding a crosswalk on Welbourne Avenue near Welbourne Nursery and Preschool, which is located across the street from the planned office development.
People associated with the preschool have expressed concerns about traffic and parking, particularly because the school, founded 100 years ago to care for Black children, is considering an expansion.
“Today we have 64 children, and we’re at max capacity,” said Beth Weagraff, a member of Welbourne’s board. “The board is now in the process of looking ahead at what does the next 100 years look like, and we are in the beginning stages and looking at plans to expand up to 100 children.”
Weagraff said the preschool has a five-year lease with Bethel AME Church for additional parking. She also described Williams, of Z Properties, as a “good new neighbor” who has helped facilitate parking agreements.
Mayor Sheila DeCiccio noted that one of the reasons the operators of the former nonprofit DePugh sold the land to William was because of his “vision.”
“That meant a lot to them,” she said.
Winter Park Day Nursery expansion approved
The City Commission also voted 5-0 to approve an expansion of Winter Park Day Nursery in the College Quarter Historic District, about a half-mile south of Welbourne Nursery and Preschool on Pennsylvania Avenue.
The plans call for a single-story, 1,025-square-foot addition and 14 additional parking spaces.
The expansion will accommodate 18 more children. The school currently serves 64 children.
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by Beth Kassab | Oct 26, 2026 | City Commission, Historic Preservation, News, Zoning and Development
Another Piece of Hannibal Square’s Black History Is Gone. Residents Want to Preserve What Remains
The City Commission is scheduled to vote Wednesday on a proposal to replace the Gardens at DePugh nursing home
Oct. 27, 2026
Beth Kassab
The historically Black neighborhood west of downtown Winter Park has undergone so much redevelopment in recent years that some longtime residents may find it nearly unrecognizable.
The latest proposed change is a complex of 10 single-story office buildings on a block in Hannibal Square that until recently was home to the historic Gardens at DePugh. The 40-bed nursing home, once one of the few local facilities of its kind available to Black families, was demolished after closing last year.
But a group of residents is determined to send a message to the City Commission, which is scheduled to hold its first vote on the project Wednesday: The neighborhood’s history is worth honoring, and what remains of it should be preserved.
“The continued redevelopment of property within and adjacent to this historic community must be approached carefully so that economic development does not gradually erase the cultural identity and history that make Hannibal Square significant,” Maria Bryant, a well-known local singer who grew up in the area, wrote to city officials in late August. “The land is still sacred to the African American community. I am requesting that the city require a meaningful historic and cultural preservation component as part of any redevelopment approval for this property. This should be more substantial than simply installing a plaque or marker after redevelopment.”
A construction fence stands around the property, but the historical marker for The Gardens at DePugh is still visible.
Near the 2.7-acre property at the corner of Morse Boulevard and Pennsylvania Avenue are several other landmarks, including Welbourne Nursery and Preschool, which was established for Black children during segregation nearly 100 years ago and continues to serve the community; Ward Chapel AME and Bethel Missionary Baptist Church, two of the city’s oldest churches; and the Ideal Woman’s Club, which was also founded by Mary Lee DePugh.
Zane Williams of Z Properties is seeking an amendment to the city’s comprehensive plan, along with new zoning, to change the property’s designation from low-density residential and allow the development of 27,500 square feet of office space at 550 Morse Blvd. He plans to sell the office buildings rather than lease them.
One rendering shows what the office buildings could look like, though multiple designs are still under consideration.
Williams said he is sensitive to the needs of the community.
“We’re certainly aware that the neighborhood is changing, and we’re sensitive to what comes with that,” Williams told the Voice in an email. “We’ve gotten to know many of our neighbors over the years, and those relationships are important to us. We understand that redevelopment brings questions, so I think the best thing we can do as developers is to be present, listen, and support the people and institutions that make up this community. We’ve already begun that process, and it’s something we intend to continue.”
The Planning & Zoning Board voted 6-0 to recommend approval of the project, subject to eight conditions. Among them: The existing DePugh historic marker must remain on the property; two oak trees must be preserved and relocated as part of the new plan, and a third oak tree measuring at least 8 inches in diameter must be added; and $100,000 must be donated to affordable housing in the city.
The $100,000 donation was prompted by the comprehensive plan amendment, which would eliminate the potential for future housing on the site. That loss triggers a fee payable to the city’s Affordable Housing and Workforce Trust Fund. Although there is no formula for calculating the fee, Williams proposed a $100,000 contribution. The money will help the city purchase a home on West Comstock Avenue for use by Habitat for Humanity.
Another rendering provides a different view of how the project could look when complete.
At least a dozen people, including real estate professionals and others who occupy properties in developments completed by Williams, wrote to the commission urging support for the proposed changes at Morse and Pennsylvania.
“Smaller office buildings available to purchase are rare in Winter Park, and they give established firms a way to own their space in the core rather than relocate to Maitland or Lake Mary,” wrote Don Wordell, chief investment officer at Ceredex Value Advisors, which moved into a property on Palmetto Avenue redeveloped by Williams. “That keeps payroll, clients, and community involvement in the city.”
Others argued that Williams’ proposal would be preferable to a much larger building that could be allowed under the city’s development code.
“The easier path on a site of this size is a single larger building,” wrote Miguel DeArcos, president of Central Parc Group. “Breaking the program into eight to ten smaller buildings is more demanding to design and build, and it is the right decision for this corner. It respects the scale of the surrounding blocks and the character residents expect from Winter Park.”
Mary Daniels, a longtime resident who received the city’s Founder’s Award from Mayor Phil Anderson in 2024 in recognition of her years of service and advocacy, wrote to the Planning & Zoning Board earlier this month that Williams needed to communicate more with the neighborhood. She also described an earlier meeting with residents as “inadequate.”
According to a city staff report, a traffic study concluded that nearby roads and intersections would continue to operate at “satisfactory levels of service.”
People affiliated with Welbourne Nursery and Preschool have raised concerns about traffic and the safety of young children walking in the area during pickup and drop-off times. They have called for additional traffic analysis.
The proposed office space would require 72 parking spaces under city regulations, and Williams’ plan provides exactly that number, according to the report.
The DePugh nursing home closed last year after its operations became financially unsustainable. Williams purchased the property for $5.4 million.
A historical plaque stands at the corner of Morse Boulevard and Pennsylvania Avenue.
DePugh opened in 1956 as the first state-approved nursing home where aging Black residents could receive care during segregation. The center was named for Mary Lee DePugh, who moved to Winter Park in 1937 to work for a white family she knew from the Chicago area. Through her work with the Ideal Woman’s Club, she began advocating for health care for people in need.
Although the building has been demolished, a city plaque still stands at the corner of the property. It recounts the nursing home’s founding, including a community fundraising effort that apparently involved Fred Rogers, the Rollins College graduate who became known to television audiences as Mr. Rogers.
“The women in the Hannibal Square community volunteered to wash laundry, cook for the patients and provided the essential daily support to keep the facility running. Today, the Gardens at DePugh Nursing Center, now a charitable 501c(3) organization, continues to offer compassionate, high quality care,” the plaque reads.
Now, however, the city may need to revise the wording to reflect the past tense.
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by Beth Kassab | Oct 23, 2026 | City Commission, News, Zoning and Development
Synagogue Proposal Faces Fresh Scrutiny as Winter Park Commissioner Defends Impartiality
Chabad of Greater Orlando is seeking to build the city’s first permanent synagogue near Park Avenue that would also include a daycare and rooftop deck
Oct. 23, 2026
By Beth Kassab
A second vote required to approve what would be Winter Park’s first permanent synagogue has been delayed again, as opponents challenge the project’s compliance with city code and raise questions about a city commissioner’s acceptance of complimentary Orlando Magic tickets from a friend who received them from the rabbi leading the project.
The City Commission was scheduled to take up the matter Oct. 28, but Chabad of Greater Orlando, the organization behind the proposed synagogue and daycare, and GAI Consultants, which is seeking to build five townhomes on the parcel, asked to postpone the hearing until Dec. 9.
Frank Santos, who says he has spent $15,000 on consultants to review the project, is aggressively contesting the proposal. He argues that it would negatively affect a townhome he owns and other nearby properties through significantly increased traffic and noise, as well as the introduction of a predominantly nonresidential use on the site of the El Cortez Apartments at the corner of Morse Boulevard and Knowles Avenue.
Santos’ attorney, former Orange County Commissioner Ted Edwards, and consultant Jeff Briggs, who retired less than two years ago as the city’s longtime planning director, have identified what they describe as “significant missed setbacks, buffers, parking deficiencies and related matters.” They also contend that the synagogue approval process must essentially start over, with the proposal returning to the Planning & Zoning Board, according to a letter Edwards sent to the City Commission earlier this week.
A rendering provided to the city shows what the synagogue could look like.
City officials did not respond to a request for comment on the letter. Rebecca Wilson, the attorney representing Chabad and GAI, has said at public meetings that the project has worked to make alterations to be compatible with the neighborhood and agreed to more than 20 conditions including no amplified noise on the roof deck and limiting the number of children in the daycare.
She has said there are more than residential uses next to the property, including a church and office and retail space.
“Your code itself says that religious institutions and daycares are allowed if we go through this conditional use process,” Wilson said on Sept. 9, noting she’s lost count of the number of conditions placed on the development but it has “proven it’s compatibility” with the neighborhood.
Santos said the townhome he purchased in 2019 on Interlachen Avenue, which backs up to the proposed synagogue property, represents a “significant investment.” He said he does not live there and does not intend to do so in the future. Instead, he lives in another Winter Park home, a little more than a mile away, north of Palm Cemetery.
“My bigger concern is the impact on downtown Winter Park and the greater area,” he said Friday.
Santos, chief executive officer of Rosen Hotels & Resorts, also said he is communicating with Jonathan Beaton, owner of the public relations firm Inside Advantage PR. Beaton reached out to Santos and offered to help his cause, citing his own concerns about traffic and parking as a Winter Park resident.
Beaton filed a public records request with the city on Sept. 12, three days after the City Commission voted 4-1 to table the second vote, with Commissioner Kris Cruzada dissenting. Commissioner Elizabeth Ingram, who had voted in favor of the project as part of a 3-2 vote in August, said she could not support it again that night because of unanswered questions about the daycare’s playground and concerns about traffic.
A map included in city documents shows the location of the property in question.
Beaton, who previously served as a spokesman for former Congressman Alan Grayson, requested a wide range of records concerning communications to and from commissioners and city staff related to the project.
The request yielded hundreds of emails involving all five commissioners, but only Ingram’s records appeared to include text messages and calendar entries.
Among those records was a text message Ingram sent to Rabbi Dovid Dubov, one of Chabad’s leaders, at 9:31 a.m. on June 4:
“Good morning, Rabbi Dubov! we had a great time at the magic game – thanks again!!! I would be happy to meet with you to discuss the synagogue.”
She also suggested a potential meeting date.
Dubov replied, “Great to hear!” and the two settled on a meeting in July.
Beaton sent the Voice a screenshot showing only that exchange last week and also contacted other media outlets.
The Voice’s review of additional records and interviews provided further context about the tickets and the timing of the communications.
Other records and interviews revealed that the Orlando Magic game in question took place in April, before Ingram said she had seen or was even aware of Chabad’s plans, which would later come before the commission. She received the tickets through a friend who had gotten them from Dubov. The tickets were among dozens of complimentary tickets Chabad distributed to promote the game, which coincided with the annual Jewish Heritage Night with the Orlando Magic.
And Ingram’s message to the rabbi on the screenshot was actually a response to a message she received from him two days earlier on June 2, the same day Chabad and GAI held a community meeting with neighborhood residents. The meeting took place about a month before the proposal was first tabled at the July 7 Planning & Zoning Board meeting.
Dubov’s June 2 message read:
“Good afternoon Commissioner Elizabeth Ingram! I hope you’re doing well and that you enjoyed our Jewish Heritage Night with the Orlando Magic back on April 6. I received your contact information [from a mutual friend] and wanted to reach out regarding the development of our first synagogue in Winter Park. As we move through the planning process, I would love the opportunity to share the vision and current plans with you, hear your thoughts, and receive your feedback as well. If you are open to meeting sometime, please let me know what works best for you. It would be greatly appreciated.”
Dubov told the Voice in a text message that Chabad has participated in the annual event with the Magic for years and has distributed “hundreds of complimentary tickets as part of our efforts to make Jewish Heritage Night welcoming and accessible to all.” He declined to answer additional questions.
Ingram, who took office in March after running unopposed, said Dubov gave the tickets to a friend of hers, and she attended the April 6 game with her family.
She said she did not hear from the rabbi again until two months later, when he contacted her after obtaining her phone number from another mutual connection, as he explained in his message.
Ingram said she nearly always agrees to meet with people who request a conversation and has also met with opponents of the synagogue proposal. Records show that she had a meeting scheduled with Santos around the same time, on July 14.
Ingram said she thanked Dubov for the tickets out of politeness because he brought them up when he initiated their text exchange.
“He never brought it up again,” she said. “Do you really think I’m going to be swayed on this huge development proposal from one Magic game months ago?”
Ingram said she learned from a reporter last week that opponents of the synagogue were raising questions about the Magic tickets. She then received a call from Santos, who suggested she might feel pressure to recuse herself from the next vote because she had accepted the tickets. He also told her there were photos of her in a suite at the Kia Center, where the Magic play.
Ingram said the tickets she received for Jewish Heritage Night were not for a suite. She said she later sat in a suite with friends and family at a different game that month, paying her own way. She said the photos Santos referenced, which were posted on her Facebook page, were taken at that game.
“He called me and said he has a lot of stuff,” she told the Voice. “I told him the whole story, and I thought, how can you say I’ve not been asking hard questions? Anyone could tell I was really conflicted over the plans [for the synagogue].”
In fact, it was Ingram’s questions on Sept. 9, before the Magic game became an issue, that helped prevent the proposal from winning approval that night and led to the vote being tabled. The other commissioners appeared divided, with two leaning in favor (Cruzada and Craig Russell) and two opposed (Sheila DeCiccio and Warren Lindsey). Those were the same positions they had taken during the first vote in August, leaving Ingram as the potential swing vote who could decide the matter.
Santos told the Voice that he made a “courtesy call” to Ingram about the tickets and photos he had been told were on Facebook.
“I told her I was getting photos of her and her family in a suite,” he said. “I’m not on Facebook. Other people are insinuating and trying to connect the dots, not me.”
Ingram released a statement Thursday evening saying she had asked the city attorney whether she could recuse herself from the next vote “because of the misleading narratives that have circulated regarding my attendance at the basketball game.”
“In no way am I concerned of my ability to remain fair and impartial,” she said in the statement. “I felt stepping aside would help prevent further controversy and avoid undermining public confidence in the commission’s final decision.”
But City Attorney Kurt Ardaman told her that elected officials are “required” to vote on matters before the commission because abstention is allowed only in cases involving a conflict of interest. Such conflicts require “a special private economic gain or loss” for the elected official, an immediate family member or the official’s employer. Ardaman said Ingram does not have a conflict of interest in this matter.
“I listen to our residents and consider different perspectives, but my decisions are my own,” Ingram said in the statement. “I believe every development application deserves fair consideration under the applicable laws and land-use standards. Political support, personal relationships and outside criticism does not determine my vote.”
Ingram also said she did not believe the tickets were worth more than $100. However, she has now filed a gift disclosure form required under state ethics rules “in the interest of full disclosure.”
Additional records provided by the city show no text messages between Ingram and Dubov after June 23 when they continued a discussion about scaling back the synagogue’s size in response to community feedback.
On June 19, Ingram had shared her concerns about the scale of the proposal with Dubov.
An earlier rendering of the synagogue shows a different style of architecture before community feedback.
“I wanted to let you know this now in case you are willing and able to work with the architect on a revised concept that would be slightly smaller,” she wrote. “I think that is going to be the biggest hurdle going into the planning and zoning meeting and then commission meeting.”
It is not unusual for commissioners to share feedback on development plans or request architectural changes.
The Planning & Zoning Board approved the project with scaled-back renderings on Aug. 4 in a 5-0 vote. One member was absent, and another abstained because he works as an urban planner and had been asked to consult on the project before the application was submitted.
Ingram also received text messages and emails from other people about the proposal, including a text from Nikki Seybold, who is working with Santos and Edwards to determine whether the synagogue project complies with city requirements for parking and setbacks. Seybold texted Ingram on the morning of Aug. 28, two days after the commission’s first vote on the project, and asked whether they could speak by phone.
“Hey Nikki! Yes, I am actually just walking out of a doctor’s appointment so I will give you a call in a few minutes when I get in my car,” Ingram responded.
Ingram said her text exchanges with Seybold and Dubov reflect her philosophy of meeting with as many people as possible to learn about city issues.
“I’m very friendly to everyone,” she said. “They might bring up something to me that I hadn’t considered.”
Santos said he has a meeting scheduled next week with Edwards, the city attorney and city staff to determine whether the proposal violates city code, as he contends.
“I don’t want to spend any more of my time or my money on this issue,” he said. “I want it to go away.”
But he said that if the city did not require all the necessary waivers to bring the project into compliance with code, that would raise questions about other developments, particularly as construction has ramped up in downtown Winter Park in recent years.
“Did the Alfond Inn apply for all the waivers? Did the Rollins museum apply for all the waivers?” he asked. “This is not just about this project; it’s about past projects and future projects.”
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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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