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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by Beth Kassab | Jun 25, 2026 | City Commission, Historic Preservation, News
Commission Approves Merrywood Lot Split on Lake Osceola
The owners and prospective buyer agreed to hold off on demolishing the estate until a required second vote by the City Commission likely later this summer
June 25, 2026
By Beth Kassab
The owners and prospective buyer of Merrywood, the nearly 90-year-old estate on Lake Osceola at the center of Winter Park’s latest historic preservation debate, agreed to hold off on demolishing the property until a required second City Commission vote that would make it possible for the large lot to be split in two.
The commission voted 3-2 on Wednesday to change the comprehensive plan to allow for a split that would only apply to 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.
The city’s rules typically prohibit lakefront lot splits, which is why the prospective buyer, Tara Tedrow, asked for a special exception in the form of a plan amendment.
While a permit is already in place would allow for the home to be bulldozed any day now, the owners and Tedrow, who has the property under contract, verbally agreed to hold off on demolition until the second reading of the comprehensive plan change — likely in about two months.
Tedrow has said she would like to build a home for her family on a portion of the nearly 4-acre lot while the other half is sold to someone who would restore Merrywood or tear it down to make way for new construction. The land is estimated to be worth more than $10 million as the single largest lot on Winter Park’s highly-sought after Chain of Lakes.
People from the community provided conflicting opinions at the meeting about whether or not the house could be restored or was beyond the point of saving. And whether the additional time agreed to on Wednesday would make a difference.
Cathy Gilmer, who owns the home with her brother, told the commission her mother lived in Merrywood from the mid 1970s until she died there about a year ago.
She was adamant that a local historic preservation designation, which would allow the city to stop demolition of the property, “isn’t ever going to be pursued.”
“No one wants to or is able to pay for it,” Gilmer said of her family home that she said is now in disrepair. “This is an unfair position to put us in, especially given the efforts over the past year to find someone to preserve the house.”
But advocates such as Friends of Casa Feliz, another Gamble Rogers showpiece that was moved, restored and now a popular destination and public venue, did not begin outreach to the preservationist community or help market the property until earlier this year.
“Casa Feliz had our first conversations with Ms. Tedrow and Mr. Mick Night [Gilmer’s real estate agent] in late January of this year and I’d say our efforts began in earnest, trying to put the word out in February of this year, so a few months,” Betsy Owens, executive director of the group and granddaughter of the architect, told the commission.
The property was considered a pocket listing, not uncommon for exclusive homes, and was never broadly advertised on the MLS or the Multiple Listing Service used by real estate professionals.
She also corrected Tedrow’s claim that Gamble Rogers grew up in a cabin that now stands preserved in her parents’ backyard, a story Tedrow has told multiple times to demonstrate her personal interest in historic preservation.
“My grandfather actually didn’t grow up in a cabin in Winter Park,” Owens said. “He grew up in Winnetka, Illinois, and moved here when he was 29.”
But Owens’ main point to commissioners is that they could resurrect the city planning staff’s recommendation to allow for a lot split on the condition that the home is designated as historic.
Planning & Zoning Director Allison McGillis based the recommendation on a previous comprehensive plan change that allowed for a lot split on New York Avenue that involved designating another lakefront Gamble Rogers house as historic while carving out a new lot from the property that is not on the lakefront. McGillis said in the case of that property, the sale of a new home on the newly created lot helped finance the restoration of the historic home.
Owens noted that city commissioners recently tasked the Historic Preservation Board with coming up with ways to encourage more people who own eligible homes to list them on the local register. There are fewer than 30 true examples of Gamble Rogers’ work remaining in Winter Park.
“Creating a valuable buildable lakefront parcel, but in return, ensure that the historic resource is not demolished … I can not imagine a more powerful preservation incentive than this,” she said. “To say we want incentives and then to reject this opportunity would be inconsistent. I also want to be fair. No one can guarantee that Merrywood will be saved if the lot split is denied. But Merrywood has never truly been tested on the open market as a preservation opportunity.”
The Planning & Zoning Board, which heard Tedrow’s proposed comprehensive plan earlier this month, opted to approve it and rejected the staff proposal that included a condition that the home be designated as historic.
The city attorney indicated the comprehensive plan change wasn’t advertised publicly as including the historic designation condition, meaning the process would potentially need to start over again.
Several commissioners said they viewed private property rights as a key issue in the debate.
Mayor Sheila DeCiccio said there is no hope to save the house and said it would be “punishing” to attempt to require it to be designated as a condition of the lot split approval.
“They have done everything they can to try to help make it happen. It has not happened … Now we want to punish them and say, well, because you wouldn’t agree to it [historic designation] we’re not going to allow the lot split … You can’t make the policy so punishing,” DeCiccio said. “When these people built the house, I’m sure in their wildest dreams they didn’t think that someone would come forward 50 or 60 years later and say, because I’m a descendant of the architect, this house needs to be designated. You can’t do that. People have a right to designate it or not. They grew up in it.”
Commissioners were also persuaded by the idea that if the lot was sold as is the house could be torn down and replaced with what would be the largest single home in the city — up to 56,000 square feet based on the acreage and city code.
DeCiccio along with commissioners Kris Cruzada and Craig Russell voted in favor of the plan to allow the lot split. Commissioners Warren Lindsey and Elizabeth Ingram voted against it.
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by Beth Kassab | Jun 22, 2026 | City Commission, Historic Preservation, News, Zoning and Development
Commissioners Voice Support for Split of Merrywood's Lakefront Lot
A vote on the lot split is scheduled for Wednesday’s City Commission meeting. Whether or not the split is approved, it appears Merrywood will be demolished.
June 22, 2026
By Beth Kassab
The City Commission appears poised to grant special permission this week for a lakefront lot to be split into two when attorney Tara Tedrow asks to divide the Merrywood property to allow for her to build a new house on Lake Osceola.
Three out of five commissioners signaled during a Monday afternoon work session that they favored the lot split that would only apply to the 3.67-acre parcel at 1020 Palmer Ave. where the largest and most ornate residence by architect James Gamble Rogers II stands, at least for now.
The more than 80-year-old house is likely to be demolished after Tedrow solicited help from historic preservation advocates to find a buyer for that half of the lot and no one came forward with an offer.
“We really tried to get the word out nationally, but certainly locally to anybody who was interested,” Tedrow, a land use attorney at the Lowndes law firm, said. “There’s a lot of people who were interested in the idea of it. Then they came, and they said no to the scope and scale of renovation, or just the cost.”
Mick Night of Sotheby’s International Realty joined the work session by phone and said he’s shown Merrywood to 100 or so people, including what he characterized as 15 to 20 people with the potential to buy the property. But no offers came in.
“You’re dealing with, aside from the condition of the house, you’re dealing with functional obsolescence, the design of the house … you know, Gamble Rogers was notorious for building lakefront homes that didn’t even take advantage of the lakefront views,” Night said. “… you’ve got a compartmentalized floor plan, you’ve got a formal floor plan, you’ve got a kitchen that is, you know, 10 by 10. I can go on and on and on, but regardless, you’re dealing with structural issues, mold issues, ongoing water intrusion issues and other things.”
He said he’s been involved in all six home sales in Winter Park that have closed above $10 million and predicted the Merrywood lot would be the seventh. He suggested the value of the land alone would be about $13 million for the 3.76 acres.
Cathy Gilmer, who now owns the house along with her brother after their parents died, wrote a letter to city officials explaining that her parents intentionally kept the house off the city’s historic register and that “the house (and the land it sits on) was my brother and I’s inheritance from them.” She said in recent years the house became “unlivable” after water pipes burst and a lack of heat or hot water because the system still runs on oil.
“Over the last year we have looked into what it would take to restore, preserve or even make the house livable again and the unfortunate fact is that we (and even the most well-intentioned preservationists who have toured the home) do not have the finances to undertake such a project,” she said. “The truth of the matter is that every day the house remains standing costs money we don’t have, falls into further disrepair and is not contributing anything to the community. It is basically a waste.”
She said her family has also been upset by recent break-ins at the home.
“On top of all of this we have had to deal with several break-ins and thefts from people who feel they have the right to take memories and pieces of our family’s history, which for anyone that has experienced anything like this knows, is an emotionally taxing experience,” Gilmer wrote. “While this might just be a house to some people, it was the house I grew up in; my family’s home. A house which everyone now has an opinion on and feels they have a right to, and yet, nobody seems to care about the people that lived and grew up in it.”
Tedrow, who grew up in a house next to Merrywood, has had the property under contract since August. She has said she would like to divide the property in two and sell one lot while building a home for her large family on the other.
The change she is requesting to the city’s comprehensive plan, a state-required document that details how a local government will manage its land and grow over a number of years, would not permit any other lakefront lot splits in Winter Park because no other existing lots meet the size requirements or zoning conditions such as 150 feet of frontage on both the lake and the street.
Commissioner Warren Lindsey, who along with Commissioner Elizabeth Ingram voiced concerns about approving the lot split, noted that there are 360 lakefront lots in the city and at least three others are also larger than three acres. Fifteen or so are greater than two acres, he said, referring to statistics he asked Planning & Zoning Director Allison McGillis to research.
While he said he cares about historic preservation, Lindsey said his larger concern is that more lakefront homeowners will come to the city seeking comprehensive plan amendments to divide their valuable lots. He called the prospect a “slippery slope.”
“Other properties may not be exactly the same,” he said. “But they could make a credible argument that they should receive consideration.”
Ingram said she was disappointed by what appeared to be a doomed fate for Merrywood and the idea that the decision came down to money rather than historic value and character.
“People just want to get the most money out of it,” she said. “Personally, I feel that can be a misconception for these houses … it does contribute to people not wanting to put their house on the historic register.”
Mayor Sheila DeCiccio along with commissioners Kris Cruzada and Craig Russell appeared in favor of the lot split and persuaded by the idea that keeping the lot at its current size would allow a buyer to knock down Merrywood and build a more than 56,000-square-foot home in its place. That would be larger than the house just down the street at 926 Palmer Ave. — dubbed “The Odyssey” by owners Marc and Sharon Hagle — that is some 40,000 square feet.
“What you’re going to get is if you get a mega house on there, you’re going to get those great big green boxes, like in the front of the Hagle’s house, that are commercial … that are so noisy that that’s the whole thing you can see when you come down the avenue,” DeCiccio said referring to the utility boxes installed on Palmer to support the large home.
Russell said he agreed that such a large house out was generally out of scale with most of the other development in Winter Park.
“It’s very delicate and unfortunate,” Russell said. “So it stinks that it’s come to this. A 56,000-square-foot-house? That’s like Drake’s house or 50 Cent’s house.”
Cruzada said he “struggled” with the decision, but ultimately reasoned the lot split is good for the city’s tax base as well as keeping home sizes in scale.
DeCiccio said she hoped a survey underway by an architecture firm for the city to catalog what historic houses remain and what has already been demolished will help in formulating a plan to save other significant homes before they “get to the point Merrywood did.”
“That’s what I see as the goal,” she said. “And this is a hard lesson that we’re having with this house, but at least it woke us up that we now have to do something.”
A vote is scheduled on the lot split request at Wednesday’s City Commission meeting.
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