by Beth Kassab | Aug 26, 2026 | City Commission, News, Zoning and Development
Chabad Synagogue Approved in 3-2 Vote
The development will also include townhomes and a daycare that some neighbors said will cause too much traffic and parking problems
Aug. 26, 2026
By Beth Kassab
The City Commission on Wednesday approved a new development near Park Avenue to include a synagogue with a daycare and five townhomes after hearing from residents about the meaning of Chabad of Greater Orlando’s work and the importance of it becoming the first permanent synagogue in Winter Park.
The 3-2 vote followed more than three hours of discussions and comments, including objections from some neighbors who said they worried the project will create too much traffic, noise and parking problems. Commissioners Elizabeth Ingram, Craig Russell and Kris Cruzada voted in favor while Mayor Sheila DeCiccio and Commissioner Warren Lindsey dissented.
“I’m willing to risk parking and I’m willing to risk traffic so people and children can have a better understanding of each other,” Cruzada said just before the vote, adding, “I’m willing to live in a little discomfort” to show acceptance in the community.
DeCiccio and Lindsey supported a motion to postpone the vote, not because they oppose the synagogue, but because they wanted additional conditions on the project such as moving the location of three parking spots closer to the townhomes and an agreement that the synagogue would hold multiple simultaneous events.
“We would welcome a synagogue in Winter Park,” DeCiccio said. “We are with you. We stand with you. Attorney [Rebecca] Wilson can tell you we do this to everybody who comes in.”
Wilson of the Lowndes law firm represents the developer of the townhomes as well as the synagogue and has logged hundreds of hours in front of the Winter Park board over years answering questions about developments down to the smallest details from a commission known to publicly dissect proposals.
When the project passed on the first of two required votes, DeCiccio suggested that before the second vote next month the developer move three parking spaces closer to the townhomes on the 0.6-acre site at the corner of Morse Boulevard and Knowles Avenue where the El Cortez apartment buildings stand today.
The El Cortez Apartments along Morse Boulevard.
Other conditions previously approved by the Planning & Zoning Board include a requirement that child drop-off and pick-up related to the daycare take place in the underground parking area planned for the synagogue as well as prohibiting speakers or amplified music on the rooftop patio; requiring all noise and lights from the rooftop end by 10 p.m.; any expansion of the synagogue or daycare must go back to the city for approval and car lines related to daycare drop-off or pick-up can not spill onto the public streets.
Rabbi Dovid Dubov said most services at Chabad have just 10 to 30 attendees. He also said the location proved the best option for Chabad because other sites proved too expensive or not in a location that people could easily walk to. 
A rendering shows what the synagogue will look like from Knowles Avenue.
The 40-year-old organization lost its Maitland building to a fire in 2024 and has been operating out of a temporary space on the far end of North Park Avenue.
The proposal calls for 80 seats in the synagogue and the daycare is limited to 60 children. The five townhomes on the site are being developed separately and will be sold once completed.
Some residents who live in nearby townhomes and condominiums questioned the accuracy of a traffic study and noted how congested the small roads already become as a result of the Methodist Church preschool across Morse Boulevard and other church schools just blocks away.
Former Orange County Commissioner Ted Edwards attended the meeting on Wednesday and said he represented Frank Santos, who lives next to the site of the project and is chief executive officer of Rosen Hotels & Resorts.
Edwards said concerns centered on the Chabad’s planned rooftop event space that he said was more appropriate for a commercial area than a residential neighborhood.
People who attend the Chabad explained that Jewish law and tradition calls for some meals and events to be held outdoors, which is the reason for the patio.
Wilson pointed out that the Edyth Bush Charitable Foundation, a three-story building just one block down from the synagogue site and across Knowles Avenue, also rents out space for events without major disruptions to traffic or parking.
WinterParkVoiceEditor@gmail.com
To comment or read comments from others, click here →
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.
WinterParkVoiceEditor@gmail.com
To comment or read comments from others, click here →
by Beth Kassab | Aug 5, 2026 | City Commission, News, Zoning and Development
Synagogue, Daycare and Townhomes Win Approval from Planning Board
A number of residents spoke for and against the project that will result in the first permanent synagogue in Winter Park
Aug. 5, 2026
By Beth Kassab
After more than 20 residents spoke out during a two-and-a-half hour discussion, Winter Park’s first permanent synagogue won unanimous approval on Tuesday evening from the Planning & Zoning Board.
While some who addressed the board expressed concerns about traffic related to a daycare that will be run by Chabad of Greater Orlando and also noise or other neighborhood disruptions from a rooftop patio proposed for the top of the building, the board members said most of their questions about the development were answered.
The P& Z board added one condition to its approval the development, which also includes five townhomes at the 0.6-acre site at the corner of Morse Boulevard and Knowles Avenue where the El Cortez apartment buildings stand today.
Board members voted 5-0 to adopt the conditions recommended by staff and add a requirement that child drop-off and pick-up related to the daycare take place in the underground parking area planned for the synagogue.(Chairman Jason Johnson and members Bill Segal, Vashon Sarkisian, Samuel King and Charles Steinberg were in favor. Member Alex Stringfellow, who works as an urban planner and was asked to consult on the project before the application was made, recused himself from the vote and member Michael Dick was absent) The other conditions include prohibiting speakers or amplified music on the rooftop patio; requiring all noise and lights from the rooftop end by 10 p.m.; any expansion of the synagogue or daycare must go back to the city for approval and car lines related to daycare drop-off or pick-up can not spill onto the public streets.
A more modern design for the new Chabad of Greater Orlando was favored by the Planning & Zoning Board.
“It’s clear that this property could be developed at a higher capacity, which is going to bring up a whole lot of issues regarding parking and traffic,” said member Vashon Sarkisian, an urban designer. “So I think we have to consider that this is, you know, a coveted area and that there’s going to be redevelopment … so what is the right use? Well, I am in favor of this use. I think it’s, like so many people said, it’s something that’s missing in the city of Winter Park.”
Earlier in the evening, Jewish residents spoke about their desire to have a synagogue closer to their homes and the positive impact of Chabad on their lives.
“Chabad has been a part of my life for a long time. It’s where my parents met. It’s where I celebrated my Bar Mitzvah, and it’s where I’ve celebrated all my holidays,” said Daniel Isaak, 16. “… It’s about allowing a community to worship where it already lives. You know, all of my Christian friends, they all have churches in their own city, and they can practice their faith close to home surrounded by their neighbors. So why should Jewish families have to leave their own community to do the same?”
The 40-year-old organization lost its Maitland building to a fire in 2024 and has been operating out of a temporary space on the far end of North Park Avenue.
Several people who attend Chabad said only 12 to 15 people typically are at Friday evening services.
The proposal, which still must be approved by the City Commission, is capped at 80 seats in the synagogue and the daycare is limited to 60 children. The five townhomes on the site are being developed separately and will be sold once completed.
Rabbi Dovid Dubov said many people who will attend services or use the daycare will walk rather than drive, which will help alleviate traffic concerns. Jewish law prohibits driving on Shabbat, for example.
“Our responsibility is to make Jewish education available where Jewish families live,” Dubov told the board. “And today, ladies and gentlemen, there is no Jewish daycare in Winter Park. We have also worked diligently to be respectful of our neighbors. We voluntarily limited our daycare to just 60 children, approximately one-fifth the size of nearby church schools, and our traffic study demonstrates that that impact will be extremely minimal.”
But some residents who live in nearby townhomes and condominiums questioned the accuracy of the traffic study and noted how congested the small roads already become as a result of the Methodist Church preschool across Morse Boulevard and other church schools just blocks away.
Frank Santos, who lives next door, said the area is already undergoing enormous change and contending with traffic and parking problems. Santos, chief executive officer of Rosen Hotels & Resorts, which has a long history of supporting local Jewish causes led by its late founder Harris Rosen, said his own rooftop living space will be impacted by as many as 80 people using the synagogue’s rooftop deck because of the proximity.
“Chabad of Greater Orlando and it’s member should have a synagogue in Winter Park,” Santos said. “Knowles Avenue is not the right location. Find a site with less density and appropriate parking.”
Marc Hagle, who is known for constructing the largest private residence in Winter Park at 40,000-square-feet on Palmer Avenue and for taking two Blue Origin suborbital space flights in recent years, said he attended the meeting with the intention of speaking against the project, but was impressed by the presentation. Still, he noted potential traffic congestion and also questioned if redeveloping the site mostly as a synagogue would have a negative tax impact to the city because religious institutions are generally exempt from paying property taxes.
“I think the tax implications to the city are a problem,” Hagle said. “The city is facing some really interesting tax problems coming up with the laws that are changing,” he noted, an apparent reference to the amendment on the November ballot that could significantly decrease property taxes collected by local governments.
The El Cortez Apartments along Morse Boulevard.
“By putting something in the area that’s tax exempt, I think you’re creating a potential problem for the future,” he said. “We’re all interested in making sure that the city meets its obligations and it maintains standards that, quite frankly, the city hasn’t done for the past five to ten years. This isn’t the right place to say this, but the quality in the city isn’t what it used to be.”
Several longtime Winter Park residents who are Jewish noted the meaning of the synagogue after a history of discrimination against Jews across the country, including in Winter Park.
“It has been a problem being Jewish in Winter Park, to be candid,” said Barry Render, a former longtime Rollins College professor. “When I moved into my house on Via Tuscany and applied for membership in the Racket Club, which is just a block away from me, I was turned down because I was Jewish.”
He also noted that the holiday celebration in Central Park did not always include a Hanukkah menorah as it does today.
David Jasmund, who lives close to the site on Interlachen Avenue, was one of several people who attended the meeting who said they were “disappointed” that any of the concerns about the development were being linked to bigotry.
“That’s disappointing,” he said. “Unfortunately, it’s around us today in society, which I think is really depressing at times.”
Jasmund said he didn’t have any concerns related to the synagogue itself, but questioned the capacity of the roads to handle another daycare in such close proximity to others.
“I think it’s unrealistic to think that someone is going to drive a 1-year-old or a 2-year-old down into a basement … take them out of a car seat, take them upstairs, and get 60 people in and out of there without it being stacked up on Morse, Interlochen, Knowles, and maybe even Park Avenue.”
Hattie Wolfe, another speaker who lives nearby, said parking in the area is already “impossible.”
A rendering shows what the townhomes on the site will look like.
“I’m Jewish,” she said. “I have nothing against the synagogue, but I don’t think it’s the right place for it, judging by what’s happening to the town.”
Becky Wilson, the Lowndes law firm attorney who is representing the synagogue and often represents development projects in Winter Park, said the project is doing everything possible to address concerns about traffic, parking and density.
“I think what occurred to me and that I’ve grown to appreciate while working on this project is how important having a synagogue in the city of Winter Park is to the Jewish residents,” she said. “And, in particular, to have one downtown where many of the other large, important churches are also located. What I’d also say to those residents is I’ve stood here for over 20 years, and I’ve never brought a project forward where I didn’t have to answer questions about traffic, parking and density.”
P&Z Chairman Jason Johnson asked Wilson if Chabad would agree to the condition that daycare pick-up and drop-off must occur in the underground garage to help with traffic flow and she said the group would agree. He suggested parking on the site is likely a “net benefit” for the downtown area once El Cortez is gone because people utilize street parking related to the apartments.
“There are people I deeply respect on both sides of the issue who have made their their comments to the board tonight,” Johnson said. “… My main concern with the traffic was not the number of trips, but rather the flow of traffic through the site for day care drop-off and pick-up. I think if that traffic flow can be directed directly into the garage below the facility, it would help alleviate that quite a bit.”
The next step for the project is a hearing in front of the City Commission.
WinterParkVoiceEditor@gmail.com
To comment or read comments from others, click here →
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.”
WinterParkVoiceEditor@gmail.com
To comment or read comments from others, click here →
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.
WinterParkVoiceEditor@gmail.com
To comment or read comments from others, click here →
by Beth Kassab | Jun 4, 2026 | Historic Preservation, News, Zoning and Development
P&Z Board Approves Controversial Split of Lakefront Merrywood Lot
One board member called the outcome a ‘special favor’ for the buyer of the ornate estate that appears fated for the bulldozer
June 4, 2026
By Kathryn Brudzinski
A split vote by the Planning & Zoning board this week gave the go ahead for one of the largest lakefront lots in Winter Park to be split in two, a move that at least one board member who opposed the split called a “special favor” for the buyer and one others decried as the probable end of the nearly 90-year-old estate known as Merrywood.
Tara Tedrow, who has the property under contract, asked the board to amend the city’s comprehensive plan to allow the 3.7 acre property at 1020 Palmer Ave. to be split into two lots. Tedrow, a land use attorney at the Lowndes law firm, has said she would like to build a home for her family on the new lot and sell the portion that includes the old vacant home that preservationists have tried to save in recent months.
The vote was 4-2 on Tuesday with Bill Segal, Alex Stringfellow, Charles Steinberg and Samuel King in favor of the amendment to allow the lot split and Michael Dick and Jason Johnson opposed. Board member Vashon Sarkisian was absent.
A sign at the edge of the driveway on Palmer Avenue helped cement the estate’s name among locals. (Beth Kassab)
The matter will next go to the City Commission for final approval.
While much of the discussion centered on if the home could be saved, Johnson said to him the issue was never about that.
“The question for me is whether the new policy that’s being proposed by the applicant is either the right way to go about getting the relief she wants or good for the city of Winter Park,” Johnson said, just prior to the vote. “My answer to both of those is no.”
He said the city’s comprehensive plan includes a policy to preserve lakefront lot estates in order to “perpetuate the unique character of Winter Park that sets it apart from other cities throughout Florida.”
“I think that policy exists for a very good reason,” Johnson added. “…The applicant is seeking a new policy that she acknowledges would apply to one single parcel of real property in the city of Winter Park. That, to me, screams special favor for one property owner, and I’m just generally against that from a policy perspective.”
A demolition application was already filed for Merrywood by owners Cathleen and Raymond Gilmer, siblings who inherited the estate from their parents, who bought the 1939 home on Lake Osceola in 1977. Tedrow facilitated the demolition permit, she said, to initiate an earlier conversation with the Historic Preservation Board to see if any ideas emerged for saving the house.
She also said extensive efforts had been made to work with “preservation-minded and historic designation-minded groups in the city and outside of the city” to find a potential buyer for the home since August. But no one stepped forward to buy the house with the goal of restoring it.
“We have put forth a significant amount of effort,” Tedrow said. “…We’ve had nearly 100 people, not open houses that anybody could come to, but nearly 100 vetted people who wanted to save this house come, and not one of them submitted an offer afterward. Everybody just wanted somebody else to do it, and that’s the unfortunate reality that we’re in.”
A view of the front entrance to Merrywood. (Beth Kassab)
In addition, she said she commissioned a structural engineering report to see if the house could be “made realistically livable,” though never submitted the report for fear of being accused of “tainting the water” regarding the sale.
“Our report shows that the foundation is settling,” Tedrow added. “There are incredible structural problems that the recommendation was not to save the house, and this company could have profited from the efforts to save a house, and it was recommended to not.”
According to the city staff’s report, Tedrow’s justification statement for the split argued the current comprehensive plan prohibition on splitting lakefront lots was “intended to prevent excessive subdivision of lakefront properties, but that the subject property represents a unique circumstance due to its size and zoning.”
Staff noted that the property’s 1938 residence was listed on the Florida Master Site File, but is not designated on the city’s historic register, leaving city officials without any power to stop demolition.
“Although the applicant’s proposal would facilitate the creation of an additional lakefront lot, staff has concerns regarding the potential demolition or loss of the historic residence, as well as the broader precedent associated with permitting additional lakefront lot splits,” the staff report reads.
Instead, staff recommended an alternative modification to the city’s comprehensive plan to allow for certain lakefront lot splits if the change is tied to the preservation and designation of historic homes constructed prior to 1950.
Johnson asked Tedrow if it’d be “safe to say” she would not be in favor of the city’s alternate proposed policy change as she’d know she’d have to designate the home as historic and would “never be able to sell that.” She said yes.
“I received an unsolicited call from a historic homeowner in the city of Winter Park, who said, ‘Just so you know, when you get your historic house on 1020 Palmer, you won’t get home insurance’,” Tedrow replied, adding the caller had said her home insurance was cancelled on her own historic home.
Some Winter Park residents disagreed with Tedrow’s claims of troubles with home insurance, like Aimee Spencer, a former member of the city’s Historic Preservation Board, who said her own 100-year-old house was able to be insured without issue. The sentiment was later echoed by John Skolfield, who serves on the historic board, who said his own home is insured despite being built in the 1920s and that Tedrow’s claim was “just not true.”
Tedrow addressed the disputes about homeowner’s insurance, stating she’d brought up the call she received as an example of issues people had presented to her as part of the home buying process.
She added that she understood the desire for the house to be saved, emphasizing that perhaps pieces of the home could be preserved if the estate is demolished.
“If the reality is this house is coming down, if there’s anything you want to save … if there’s parts you want to salvage and take for something, we are open to all of that,” Tedrow said.
Others spoke in support of the lot split, like resident Scott Peelen who said he resides about 1,000 feet from Merrywood and believed the proposal to be a good solution for the “blighted area.”
“It’s been run down for a long, long time,” he said. “I know everyone in this room is here because they love Winter Park…All of us want what’s best for it.”
Support also came from some on the board, such as board member Bill Segal who said he understood the love for the city’s historic homes but that the board’s job was to do what’s best for the city.
“They mean a lot in Water Park, but the public doesn’t own it — it’s privately owned,” Segal said. “Some members of the public really strongly want to preserve this thing, and we heard some of them tonight, but I walked through this home…it’s just in terrible shape, so I think we just need to get rid of this idea that [it’s going to be saved].”
Skolfield, who owns the construction and renovation firm Skolfield Homes, disputed the idea that the home couldn’t be saved, saying it simply came down to price.
“Merrywood is realistically livable — maybe not for $15 million, but it can be done,” Skolfield said. “…It is possible. It may not make the world’s best financial sense. But you know, when we’re on our deathbed, is that really what’s going to matter? Maybe the art matters, too.”
WinterParkVoiceEditor@gmail.com
To comment or read comments from others, click here →
Recent Comments