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 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 | 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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