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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by Beth Kassab | Aug 3, 2026 | Historic Preservation, News, Zoning and Development
New Synagogue, Daycare, Townhomes to go before Planning & Zoning Board
Chabad of Greater Orlando is looking for a ‘forever home’ but some nearby residents worry about traffic associated with a new daycare
Aug. 3, 2026
By Beth Kassab
On Tuesday evening the Planning & Zoning Board will hear a proposal to replace apartment buildings that date back 100 years just off Park Avenue with a synagogue, including a daycare, and five townhomes.
The new synagogue would provide a “forever home” for Chabad of Greater Orlando, said Rabbi Dovid Dubov, and would be the only synagogue currently operating in Winter Park.
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.
“We look at it like it’s overdue,” Dubov told the Voice. “It’s something that many, many Jewish residents of our city have been desiring for a long time … we’re excited.”
A new elevation submitted to the city shows what the synagogue could look like from Knowles Avenue.
A number of residents expressed concerns about the development — not because of a new house of worship — but because they said the original architectural renderings seemed “out of place” and worry about future traffic caused by the daycare.
About 50 people signed a petition that calls on the Planning & Zoning Board to reject the daycare component of the proposal at 210 Morse Boulevard.
“The addition of a daycare center or preschool would generate substantial vehicle traffic during peak morning drop-off and afternoon pick-up periods, increasing congestion, creating safety concerns for pedestrians and motorists, and adversely affecting neighboring residents and businesses,” the petition reads.
Allan Keen, a well-known Rollins college trustee and developer whose credits include Winter Park’s Windsong neighborhood and work assembling land for Universal Orlando, wrote a letter to city officials last month that said the area is already too congested.
“Our residents, and all of the other residents of Winter Park, are already burdened with several daycare and/or church-run schools in the immediate area (Methodist, Congregational and Catholic), that at times, completely block the traffic on Morse, and Interlachen,” wrote Keen, who lives across Knowles Avenue from the proposed synagogue and townhomes in a condo building known as The Landmark, which he also developed.
A traffic analysis cited by city planners concluded that the project is “not anticipated to impact the operations of the surrounding roadway network.”
Keen also wrote that the elevation of the synagogue on Knowles “is over-done and looks greatly out of place.”
An earlier rendering of the synagogue has since been updated.
New elevations submitted to the city show a more modern-looking design with more windows and without large columns.
The proposal, which is about .6 acres in total, calls for El Cortez, three buildings that date to the 1920s with 38 units to be demolished and replaced by five new townhomes as well as an 80-seat synagogue and a daycare capped at 60 children.
The property is within the Interlachen Avenue Historic District and the Historic Preservation Board approved the demolition last year and required a historic marker be added to the site and that the demolition not occur until a building permit is issued for the new development.
The El Cortez Apartments along Morse Boulevard.
The buildings were originally constructed as upscale apartments amid growing demand for more housing in downtown Winter Park and near Rollins College. Over the years, a number of notable people lived there, according to National Register of Historic Places documents, such as “physician Benjamin Hart; Christopher Honaas, director of the Rollins College Conservatory of Music; Flora Magoun, secretary to the Conservatory; Margaret Windau, district director of the Florida Welfare Board; Helen Drinker, proprietress of a women’s fashion shop on Park Avenue North; and William Stein, a Romance Languages professor at Rollins College of Jewish descent who had recently immigrated from Austria to avoid Nazi persecution.”
City staff is also recommending seven more conditions be placed on the new development including that a rooftop deck for the synagogue not include outdoor speakers or amplified music; all noise and lights from the rooftop must 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. Planning & Zoning will hear the proposal at 5 p.m. on Tuesday.
A map included with city documents shows where the proposed project will be built.
The townhomes, which are being developed separately from the synagogue, will include underground parking garages. The synagogue will also include underground parking with 22 spaces and 13 more surface parking spaces on the site.
Dubov said his organization is small and the synagogue and the daycare will not operate during the same hours, which will lessen traffic and mean that the planned parking will be sufficient. In addition, he said many people will walk instead of drive to the building for services because many observe traditional Jewish laws that prohibit labor, including driving, on Shabbat.
He said the location at Morse Boulevard and Knowles Avenue will provide a central meeting spot that people can reach on foot from across Winter Park, which is known for its walkability.
“We felt like this was the most convenient location for everyone … a middle ground for everyone to give people the convenience to walk from any point,” Dubov said.
He said he doesn’t anticipate frequent events on the rooftop terrace and sees it like a backyard for the organization because Jewish tradition calls for some events or meals to take place outside.
He also said the organization doesn’t carry a traditional label that accompanies many synagogues such as orthodox, reform or conservative. The group’s website notes it is dedicated to “strengthening Jewish life through meaningful educational opportunities, inspiring programs, volunteer initiatives, pastoral care, and community services.”
“We accept everyone from all backgrounds,” Dubov said. “There’s no specific type of Jew we welcome or don’t welcome.”
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by Beth Kassab | Jul 27, 2026 | City Commission, Historic Preservation, News
So Far, No Response to Matt Morgan's Offer for Merrywood
The attorney and Winter Park resident now says he is willing to pay $12 million for the property in hopes of preserving the historic home
July 27, 2026
By Beth Kassab
Matt Morgan, who increased his offer this month from $10 million to $12 million for Merrywood, says he has not received any response from the sellers.
That means the future of the nearly 90-year-old estate designed by James Gamble Rogers II remains in limbo as an August vote nears for the City Commission to decide if the current buyer with a contract on the property will be allowed to split the large lot on Lake Osceola in two. Winter Park’s land development rules generally prohibit subdividing lakefront lots so Tara Tedrow, the buyer with the contract, is seeking special permission.
Morgan told the Voice he has not heard back since putting his offer in writing more than two weeks ago.
Mick Night, the Sotheby’s real estate agent handling the transaction on behalf of the longtime owners and for Tedrow, did not respond to requests for comment. Tedrow also did not respond to messages seeking comment on Morgan’s offer.
A demolition permit remains posted at 1020 Palmer Ave., though city officials say a list of tasks that must be done before the bulldozers roll in have not yet been completed such as certifying the water and power is shut off, an inspection for pests and draining the air-conditioning system.
A demolition permit is posted outside 1020 Palmer Ave. (Photo by Gabrielle Russon)
Morgan, a Winter Park resident known as a key face of the Morgan & Morgan law firm, first 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.
The Voice first reported his offer earlier this month after Morgan came forward in response to news reports that the house was all but guaranteed to be torn down after Night told the City Commission that no one wanted to pay to maintain it despite nearly a year of searching by himself, Tedrow and local preservationists for a way to keep Merrywood. The City Commission voted 3-2 on June 24 in the first of two required votes to approve the lot split.
Shortly after that meeting, Morgan said his original offer still stood and then increased what he said he is willing to pay to $12 million, a price he said he based on his understanding of the amount Tedrow agreed to pay under her contract that is contingent on the city approving the lot split.
“In my view, my offer solves all of the current problems,” Morgan told Mayor Sheila DeCiccio and commissioners in an email on July 10. “Tara Tedrow has expressed her desire to have the historic home preserved and also build a personal residence on the other lot, which is very close to her childhood home. At the time of the hearing, my desire to preserve Merrywood was not known. After hearing there was a strong desire to preserve the home by the contract holders, I immediately came forward to offer this solution. My current offer is pending and I have not heard back yet, but I am very optimistic. My offer allows [current owners Ray and Cathy Gilmer] to receive their current contract price either which way.”
He said he would be willing to purchase the entire lot or a portion of the lot, if the split is allowed, that is needed to keep the home in place.
“I am offering to purchase the estate portion at the same pro rata value established by their own contract while preserving one of Winter Park’s most significant historic homes,” Morgan wrote. “The city no longer has to choose between fairness to the owners and preservation of Merrywood. It can accomplish both without changing its Comprehensive Plan for a single property.”
Morgan’s email to city officials was in response to an email from Night to the mayor and commission with the subject line “Merrywood Rumors.” Morgan said Night is a “man of integrity” in response to Night’s defense of his assertions to the City Commission that there were no alternatives to demolishing Merrywood.
“First of all, I stand by any representations at the recent June 24 hearing about the lack of interested buyers or offers to preserve Merrywood, regardless of errant rumors being circulated surrounding the Matt Morgan offer made last August 2025,” Night wrote.
He went on to explain that he did not discuss preserving the home with Morgan at the time of the original offer last year and that the sellers did not consider $10 million “within the range of what they were willing to sell the property for, then or now.”
Those points were reported in the Voice story about Morgan’s offer on July 6, four days before Night’s email to city officials.
“Matt and I have spoken several times in good faith this week, with a mutual interest in continuing to do anything either of us could to save Merrywood, in addition to the collective and well-publicized ongoing efforts for almost a year now,” Night wrote on the afternoon of July 10.
In Winter Park, the local historic register offers protections against buildings being demolished. But joining the register is voluntary and must be done by the owners. In the case of Merrywood, the longtime owners deliberately kept the property off the register in the event it would be worth more as a tear down.
The city’s historic preservation rules do not govern or prohibit interior renovations and apply to the look and materials on the exterior.
Vacant land on Winter Park’s picturesque chain of lakes is scarce.
But how much the property is worth has been the subject of varying views during the discussions over whether the home should be saved.
Night said at a public meeting that the entire lot is estimated between $13 million and $15 million. He said during a June 22 work session with the city commission that it would be just the seventh transaction higher than $10 million in Winter Park.
Commissioner Elizabeth Ingram asked Tedrow during the June 24 meeting what a “realistic amount” would be for the portion of the lot that included Merrywood if the lot was divided into two pieces.
“Real estate prices are going to be determined on a per acre basis,” Tedrow said. “And if you look at market comps, again I don’t set market comps those are set by recent sales data … I mean, you’re looking at just for the Merrywood site, you are over $12 [million].”
It’s unclear how Tedrow’s figure for just a portion of the lot of more than $12 million reconciles with Night’s estimate of $13 million to $15 million for the entire lot and the reported price of $12 million for the contract held by Tedrow for the entire lot contingent on approval of a split.
City officials allowed one other lakefront lot split in recent years that also involved a Gamble Rogers home, but with two key distinctions from Tedrow’s request. In 2024, the commission changed the Comprehensive Plan in a way to allow for a lot split at 1290 N. Park Avenue, but in that instance the newly created lot was not on the lakefront and the owners were required to designate the existing 1930 home on Lake Maitland as historic on the city’s register.
City staff recommended approval of Tedrow’s request also come with a condition that Merrywood be designated historic, but both the Planning and Zoning Board and City Commission rejected that condition after they were told by the owners, Tedrow and Night that the home is in disrepair and no one was willing to purchase it and restore it. Morgan made his offer public after those votes.
The number of Gamble Rogers houses in Winter Park is shrinking each year as they are torn down for new construction. Fewer than 25 quality examples are estimated to remain.
Gamble Rogers is also known for designing the Florida Supreme Court, Olin Library at Rollins College and Greenada Court on Park Avenue, a Mediterranean-style courtyard with a fountain and tables often occupied by shoppers sipping Barnie’s Coffee. Casa Feliz, one of his most well-known works because it’s now a popular event venue and museum, was nearly torn down 25 years ago until the community rallied to raise money and move it to its current post just off the Winter Park Nine.
His body of work resulted in Gamble Rogers being credited with influencing the aesthetic and feel of Winter Park, which the New York Times has described as “more like a village than a suburb” because of its elevated planning, design and walkability and as a “sophisticated alternative to Disney.”
“As with [Frank Lloyd] Wright’s work in Oak Park, Illinois, and [Addison] Mizner’s work in Palm Beach, Rogers’ work in Winter Park created an architectural character for the town,” wrote Patrick W. McClane and Debra A McClane in “The Architecture of James Gamble Rogers II,” which featured a section on Merrywood. “It can be argued that the publication of many of his designs also exerted at least some influence on a national level by exposing Florida architecture to a national audience.”
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by Beth Kassab | Jul 6, 2026 | Arts and Culture, City Commission, Historic Preservation, News
Matt Morgan Offered $10 Million for Merrywood
The attorney and Winter Park resident said he would like to preserve the house. The real estate agent for the sellers said the offer was too low.
July 6, 2026
By Beth Kassab
Matt Morgan, the Morgan & Morgan attorney who lives in a home on Winter Park’s Historic Register, said he made a verbal offer of $10 million last year to purchase the entire Merrywood lot and reinitiated the offer last week with, he said, the intention of preserving the nearly 90-year-old estate that is significant because of its age and as the largest and most ornate home built by architect James Gamble Rogers II.
Morgan’s original offer wasn’t included in the information provided to the City Commission before the elected board took its first vote June 24 on the fate of property. The commission voted 3-2 (commissioners Elizabeth Ingram and Warren Lindsey dissented) for a change to the land development plan that would allow for the 3.67-acre lot to be split in two without requiring a condition recommended by city staff that the existing home be placed on the city’s historic register.
Mick Night, the real estate agent handling the transaction, said the sellers considered Morgan’s offer to be too low. He said he didn’t include the information in his discussion with the commission because he never had a conversation with Morgan about saving Merrywood.
“There was never a discussion with Matt about preserving the house a year ago,” Night said. “His offer was for the land.”
Morgan agreed that such a discussion did not take place. He added that his offer at the time was not contingent on a lot split and that he is interested in seeing the home maintained.
Lakefront lot splits are generally prohibited by Winter Park, which is why the amendment to the comprehensive plan is required. The change requires a second vote after the state takes 45 to 60 days to review the amendment, likely landing the next time the City Commission considers the matter sometime in August.
A greenlight for the lot split would pave the way for the old house to be demolished — a demolition permit is already active and set to expire Aug. 31 — and two new lakefront homes to be built in its place.
“They [the City Commission] heard there’s no other options … yes there is,” Morgan told the Voice after reading news stories about the vote. “If I see a bulldozer pull up to that house and I didn’t say something, it would bother me.”
Commissioners were told that more than 100 people toured Merrywood and not a single person was willing to purchase and preserve the home because it was too expensive, required too much work or both. Commissioners heard about the attempts to market and sell the estate from one of the sellers as well as the prospective buyer who has the property under a contract that is contingent on the lot split receiving final approval and Night, the Sotheby’s real estate agent who represents them both.
Morgan walked through the home with Night nearly a year ago in early August just as the property became available. Morgan said that a short time later he sent Night a voice memorandum communicating the $10 million offer that he says was not contingent on a lot split. By the time Morgan heard back from Night, he said it was early September and Night told him that that the property went under contract shortly after Morgan toured the estate.
That contract belongs to Tara Tedrow, the land use attorney with the Lowndes law firm who grew up next door to Merrywood and applied for the comprehensive plan change that would allow the lot to be split in two so that she could build a home for her family on one portion while the other is sold.
Night said $10 million was too low for Cathy and Raymond Gilmer, the siblings who inherited the property when their parents, who had lived in the home since 1977, died.
“That was not a number the Gilmers, last summer or anytime since then, have ever been open to selling the property for,” Night said.
Night declined to give the price of Tedrow’s contract on the lot. During a public city work session on June 22 he estimated the land value of the lot to be in the range of $13 million to $15 million.
Night told the City Commission that, while he never listed the home on the MLS, more than 100 people toured the property, including what he estimated to be 15 to 20 people qualified to make such a high-dollar purchase and that none offered to preserve Merrywood.
“All left the property shaking their head, hands in their face,” Night said during a June 22 work session with the City Commission. “They just don’t see it. We haven’t had traction with one buyer.”
Two days later at the regular Commission meeting, Mayor Sheila DeCiccio asked Night: “Is there anyone interested in purchasing that home?”
He replied, “The answer is no. Not one of the viable buyers, much less anyone else, left that house and said, ‘Wow, there’s so much potential here.'”
Night told the Voice on Monday that his comments at the commission meetings intended to convey that he didn’t receive what he considered to be “bona fide offers.”
“There have been many offers,” he said, but none have been “anywhere near reality” on price.
At one point in the June 24 meeting, Tedrow suggested that the price of the Merrywood portion alone would be about $12 million if the lot was split. It’s unclear how that figure is reconciled with Night’s estimate that the land value of the entire lot is at least $13 million.
Morgan said if the city allows the lot split without assurance that the house is preserved then “the city gives everything and gets nothing in return.”
“If the city voted to allow this, they are voting to allow all residents to split lots in the future and get nothing in return,” Morgan said. “It would be one thing if there was some type of meaningful consideration for the city in exchange for the lot split, most notably, preservation of a very important historic home to the city. However, as currently contemplated, in my opinion — the buyers would likely make a meaningful profit and the people (the city) would get nothing in return.”
Morgan isn’t inexperienced when it comes to historic homes. He spent $10.5 million in 2022 for a house that sits on about 3 acres on Winter Park’s Lake Maitland, according to property appraiser records. The 1926 home was designed by Maurice Kressly, another notable local architect, and was placed on the city’s historic register in 2002 by previous owners. It is larger than Merrywood at about 10,000 square feet.
He told the Voice that his original $10 million offer for the entire Merrywood lot still stands and that he made a second $5.5 million offer on Friday to purchase a portion of the lot and preserve Merrywood.
“I think it’s important to the community that the home not be torn down,” Morgan said in a text message to Night on Friday that he shared with the Voice. “For that reason, I am offering to purchase the Merrywood estate for 5.5M. We can split the lot at 1.835 acres each parcel and the current contingency contract holders can build their home on their 1.835 acre lot. I will make a covenant to the city that I will not tear the house down … Alternatively, my offer for 10 million for the entire parcel stands.”
It would be difficult or impossible, according to documents filed with the city and public discussion, to split the lot exactly in half with a straight line from Palmer Avenue to the lake without removing a portion of the Merrywood house that was added on in the 1960s as well as a portion of the swimming pool.
Morgan said if he purchased the entire lot he would also want the ability to split it in the future, but his interest didn’t hinge on that.
“I said of course I’d love that optionality [of a lot split] if I could get it, but it’s such incredible land and such an incredible house that wasn’t a contingency for me,” Morgan said.
He agreed the home is in need of a lot of work and would be expensive to restore. He said if he was the buyer he would look to renovate Merrywood over a number of years and not right away.
The chairman of the board of Friends of Casa Feliz, a group that advocates for preservation and worked with Tedrow and Night to get the word out about the house in hopes of finding a buyer, said news of Morgan’s offer is “extraordinarily encouraging.”
“It demonstrates what many preservation advocates have said from the beginning: Merrywood can be saved, and there is a real market in Winter Park for significant historic properties,” said a statement from Chairman John Bill.
He urged the City Commission to make saving Merrywood a condition of the approval of a lot split.
“To reward the demolition of this resource, now that there is a demonstrated buyer, with a change to our comp plan without requiring designation, would be unconscionable,” the statement said.
At the end of the discussion during the June 24 commission meeting, Tedrow said the sellers were willing to wait until the next vote before they demolish the house even though they are permitted to do so anytime.
DeCiccio said the agreement would “give another 45 to 60 days for someone to come forward for that property and purchase it and designate it historic so we’re buying more time.”
It remains to be seen if Morgan’s offer will be enough, if another buyer will step forward or if Merrywood will be the latest Gamble Rogers house to be reduced to photographs in an archive.
Night and Morgan are planning to meet to discuss the property.
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