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.
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.
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.
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.”
Historic Preservation Disagreements Pile Up: Spend Money on a Consultant? Offer Tax Incentives?
The City Commission this week touched off what is likely to be a contentious debate over how — or even if — property owners should be encouraged to place historical assets on a local register to help protect them from demolition
May 29, 2026
By Beth Kassab
Preservationists pleaded with City Commissioners this week over what is likely to be only the first disagreement as Winter Park endeavors to save more houses from the bulldozer: Whether the Historic Preservation Board should be able to spend money on a consultant as it works to make recommendations tasked by the commission.
The request was simple: Hire an expert to help evaluate what’s been lost, what’s still worth saving and how to go about keeping more old homes off the rubble pile.
But preservation debates in the city have a long tradition of drawing entrenched camps in which one side argues private property rights trump all else and that public dollars shouldn’t be used on private assets while another side says each teardown irreversibly erases a piece of the charm, eclectic architecture and history that makes Winter Park so unique and desirable.
The latest round of preservation talks are complicated by the backdrop of the Florida Legislature’s special session next week that could result in a proposal to significantly decrease property taxes collected by local governments such as Winter Park to pay for needs such as police, fire rescue, parks, roads and more.
“I don’t think history can just live on a plaque or marker, it has to be seen and observed,” said Commissioner Elizabeth Ingram, who said during the discussion at Wednesday’s commission meeting that she supported hiring an expert to focus on the task of forming a historic preservation strategy for the city. “I don’t believe the Historic Preservation Board can do this on their own … they could put out a call for guidance and start planning for creating this position for historic preservation.”
Ingram noted that other cities have designated historic preservation officers with specialized expertise that members of the volunteer advisory board may not have.
Mayor Sheila DeCiccio almost immediately threw water on that idea.
“But how are we going to pay for a person, Commissioner Ingram? Where do we get the money?” DeCiccio asked.
Earlier in the meeting the mayor said the property tax reform being pushed by Gov. Ron DeSantis could mean, “We’re not going to have any more taxes … I don’t know how we are going to keep the roads going … keep City Hall going?”
Betsy Owens, executive director of Friends of Casa Feliz, countered that local governments make funding choices all the time when something matters.
“We find room in the city budget for a lot of things we value,” she said. “We spent $200,000 today to undo a mistake that was made on the golf course … Heaven help us if we can’t find a few thousand dollars to hire a respected consultant to guide us through this process and help us out of this quandary.”
Earlier this month the city shut down the Winter Park Nine after the wrong chemical was applied to the course, killing off the grass. On Wednesday the commission approved a $197,000 course maintenance contract for four months — or nearly $50,000 per month. City Manager Randy Knight said the purpose was to test whether staff should farm out golf course maintenance or keep it in house.
The longtime owners are selling the property and the contracted buyer is seeking special permission to split the lot in two so that the Merrywood portion can be sold off again and a new home can be constructed on a new lot next to it.
Without a buyer willing to restore Merrywood, it appears destined for the bulldozer whether or not the Planning & Zoning Board approves the lot split request at a hearing scheduled for next Tuesday at 5 p.m. And, so far, no buyer has emerged, Owens said.
People who showed up to speak on the matter at Wednesday’s meeting lamented the potential loss.
Carolyn Gould, who has lived in the city 70 years, said she recalls riding her bike down Palmer Avenue past Merrywood and the wonder it inspired even from the driveway gate.
“When it’s bulldozed it’s gone,” she said. “You need to walk through those rooms and look through those windows … the moldings and appointments are just one-of-a-kind … I’m on fire about this for some reason. We have to get busy and do something.”
Daryl Carter, who purchased and renovated a Gamble Rogers house on Palmer Avenue in recent years, said most people who looked at the home considered tearing it down.
“We did not,” he said. “Our house doesn’t have a historic designation. We did what we did voluntarily … we love beauty, but we’re also private property owners and believe in private property rights. I hope this board will take that into consideration and not take private property rights from owners.”
While some cities designate properties as historic without an owner’s consent, no one is suggesting such a policy change in Winter Park.
The discussion is more about how to offer additional incentives to urge more people to seek historic designation if their property qualifies. The city has the ability in its code already to provide tax exemptions to historic properties, though no one appears to be taking advantage of that as of now, said Planning & Zoning Director Allison McGillis. The city also offers a 50 percent matching grant for renovation work that qualifies, up to $18,000, she said.
The local historic register and designated historic districts do not outright prohibit demolition in Winter Park. But the request must be approved by the Historic Preservation Board. The board does not have control over interior renovations — only major changes to the facade of the structure.
Those who designate their homes often receive special permission for variances during a renovation that wouldn’t be allowed in a non-historic structure and they are also allowed to add accessory dwelling units (such as a small rental or mother-in-law suite) to their properties.
“We have the easiest to skirt around ordinance in the entire state of Florida,” said Aimee Spencer, a former member of the Historic Preservation Board who lives in a 102-year-old house. “Even Quincy, Florida out does us in their preservation standards,” she noted of the Panhandle town of fewer than 8,000 people.
She said Winter Park needs better rules and also education against misinformation circulating about historic homes such as how they are ineligible for financing or insurance.
“I have a typical mortgage and homeowners insurance with State Farm,” she said. “It’s not a problem to insure or finance.”
Kelsey Wolfe, who serves on the preservation board, noted the board is all volunteers with related skills and a passion, but not necessarily the professional expertise needed to prepare a comprehensive strategy to shift the direction from tear downs to preservation.
“We’ve spent countless hours making changes to the ordinance already and we are waiting on a survey that hasn’t been done in 20 years and we brainstorm every meeting and work session about the very thing you’re officially charging us with,” Wolfe said. “The vast majority of our ideas and requests don’t get implemented because we don’t have the help or the budget.”
She noted that the McGillis, the staff person devoted to the Historic Preservation Board also oversees all of Planning & Zoning for the entire city.
The commission remained unmoved, however, and voted 4-0 to charge the advisory board with formulating recommendations without, at least for the time being, any additional resources.
WinterParkVoiceEditor@gmail.com
CORRECTION: This story has been updated to reflect Winter Park’s current property tax exemption and matching grant program for historic properties that qualify.
Preservation Advocates Say Winter Park Must Do More to Save Historic Homes
With three John Gamble Rogers II homes under threat of demolition this year, advocate says dwindling assets should serve as ‘wake up call’
May 14, 2026
By Beth Kassab
With three homes designed by James Gamble Rogers II currently under threat of demolition, historic preservation advocates pleaded with the City Commission on Wednesday to make meaningful changes to the way Winter Park protects its historic assets.
Betsy Owens, executive director of Friends of Casa Feliz and granddaughter of Gamble Rogers, said she hopes the potential loss of three significant houses — all more than 85 years old — in a single year will serve as a “wake up call” for the city to strengthen its historic preservation ordinance. She said the city’s ordinance is among “the weakest in the state.”
“These are not anonymous old buildings,” Owens said. “They are irreplaceable works by the architect who more than any other helped define the visual character of Winter Park.”
None of the three homes are listed on the city’s historic register, meaning there is no protection from demolition. The register is voluntary and many owners deliberately opt to keep homes off the register under the theory that the home will be worth more without demolition restrictions.
Owens, and other advocates who spoke at the meeting, including Jack Rogers, said it’s time for Winter Park to get serious about preservation.
They are recommending the commission consider adding incentives such as property tax breaks or rehabilitation help for people who list their homes on the register. They are also calling for new ideas such as an investment fund to help with purchasing and then reselling historic homes to people who are willing to invest in and preserve them.
Mayor Sheila DeCiccio recommended a discussion about potential changes be added to the next City Commission meeting on May 27 and the other commissioners agreed. The commission would likely send the matter to the Historic Preservation Board for further evaluation before making a final decision on changes.
The homes currently under threat are:
1020 Palmer Avenue, also known as Merrywood, which is under active demolition permit and could be demolished by the end of May. The home is one of the largest and most ornate in the dwindling collection of Gamble Rogers homes. Tara Tedrow, the prospective buyer who has the property under contract, facilitated the demolition permit in March and is also asking the city to amend its comprehensive plan to allow the lakefront property to be split into two lots. Under that scenario, she said, she would attempt to find a buyer interested in restoring Merrywood while her family could build a new home on the other portion of the property. A Planning & Zoning Board hearing on the request was delayed at Tedrow’s request until June. “Despite enormous public interest and dozens of interested investors touring the property, no buyer has yet emerged able to reconcile the nearly $10 million (estimated) asking price with the substantial restoration needs of the house, conservatively estimated at more than $3 million,” Owens said in an email to supporters.
250 Virginia Drive sits on a large lot overlooking Lake Virginia. The home was sold last year for $2.6 million and a demolition permit was filed by the new owner last month. The home is considered an example of the Colonial Revival style with strong New England influences, including shaker shingles.
617 Interlachen Avenue is possibly “the most eclectic and artistically ambitious of Rogers’ Spanish Eclectic residences. There is no demolition permit filed yet, but Rogers said the home is expected to go up for sale soon and in one of the city’s most expensive neighborhoods. “History has shown that when the dirt beneath a home becomes worth many multiples of the structure itself, it is time for that home to get its affairs in order,” she said.
Orange Signs Herald May as Historic Preservation Month
Residents display their yard signs each year in support of maintaining what’s left of the pockets in Winter Park where 100-plus year homes are commonplace
May 1, 2026
By Beth Kassab
It’s that time of year when orange yard signs start sprouting up in yards all over Winter Park to mark May as Historic Preservation Month.
The signs are a longstanding tradition among preservationists who want to remind Winter Parkers of the benefits of preserving historic architecture and the eclectic charm that keeps the city at the top of the charts when it comes to home values.
Historic districts in the city include College Quarter, Virginia Heights East, Interlachen Avenue and the downtown area centered on Park Avenue.
The city encourages those with designated homes or those who live in the districts to display their signs.
People who need a sign can pick one up at Casa Feliz on any Tuesday, Wednesday or Thursday from 10 a.m. to 2 p.m., said Betsy Owens, executive director of the Casa Feliz Historic Home Museum and a leading preservation advocate in Central Florida.
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