Lot Split Request Puts Future of Gamble Rogers Estate in Question
Lakefront lot splits are against Winter Park policy. But the prospective owner of the largest lot on the city’s esteemed chain of lakes says the alternative could be worse — a residence so large it dwarfs the Library & Events Center
Feb. 7, 2026
By Beth Kassab
The fate of 1020 Palmer Avenue — a once-grand home and among the largest and most ornate ever designed by James Gamble Rogers II (think velvet-covered handrails) and known in recent years as “Merrywood” — appears to hinge on whether a unicorn buyer emerges to save the property.
Such a feat would take not only millions of dollars, but also approval from city officials to break one of Winter Park’s cardinal development rules: No lakefront lot splits allowed.
Tara Tedrow, the prospective buyer who has the property under contract, is asking for an exception to that rule to allow the 3.67-acre lot — the largest property on the picturesque Winter Park Chain of Lakes — to be divided into two lots on Lake Osceola. Each lot, she said, would be at least 150 feet wide and 1.5 acres or larger.
Zillow estimates the property at $12.1 million while other estimates, such as Redfin, list it at $6.4 million.
Tedrow, a land-use attorney at Lowndes who also used to practice cannabis law there, could then potentially sell the lot with the existing home and build a new home for her family on the newly created lakefront lot. The exception would be written in such a way that it would apply only to her lot and no others, according to city staff, because the lot Tedrow wants to purchase is the only one large enough.
The name “Merrywood” at the start of the driveway at 1020 Palmer Avenue.
While she told the Planning & Zoning Board earlier this week that she believes the currently vacant home is beyond repair, she said she is open to talking with buyers interested in restoring the 7,000-square-foot structure, which dates back to 1940.
She also met with Betsy Owens, granddaughter of Gamble Rogers and leader of the Casa Feliz Historic Home Museum — a Gamble Rogers home and now a popular event space that was famously moved from Interlachen Avenue to just off the ninth fairway of the Winter Park Nine 25 years ago after it was threatened with demolition.
“I’m certain if I’m not in the picture, that the house will get torn down,” Tedrow told the P&Z board earlier this week of the Palmer Avenue home.
The house at 1020 Palmer Avenue is not on the city’s historic register because the longtime owners chose to keep it off. It could be destroyed with a simple demolition permit. However, the property is listed on the Florida Master Site File, a state database of historical and cultural resources, which means the city’s Historic Preservation Board could delay a demolition request for 90 days to allow time to consider alternatives or ways to preserve pieces of the home.
The P&Z board voted 4–2 on Tuesday to grant Tedrow’s request to delay the hearing on the lot split until June — so far, there is no demolition request — to give her time to see whether anyone comes forward who may be interested in restoring the property.
“We appreciate the opportunity to present this case to the city and to hear from our neighbors and members of the historic preservation community,” Tedrow told the Voice. “Having grown up in Winter Park, I appreciate just how unique and beautiful the city is. As I am expecting my third baby in three years, I want more than ever to move back to Winter Park.”
Alex Stringfellow, Bill Segal, David Bornstein, and Charles Steinberg voted in favor of granting the continuance.
Jason Johnson, chairman of the P&Z board, and board member Michael Dick voted against continuing the hearing on the lot split. Both expressed skepticism that a lot split — which would require a change to the comprehensive plan that governs how the city will develop in coming years — should be granted.
The rule states that a property owner cannot divide a lakefront parcel into two and build a house on each one. Such splits would increase density and development along the shorelines of the city’s lakes and decrease the diversity of lot sizes central to the city’s unique character.
The only exception in the plan — which does not apply in this case — is when there is a lakefront lot with a house that is historically designated and older than 1950, and the lot split does not create a new lakefront lot, said Planning & Zoning Director Allison McGillis. In such a case, which occurred last year with another Gamble Rogers house on North Park Avenue, one lot remained on the lakefront while the newly created lot was not on the water.
A view of the home from Palmer Avenue.
McGillis told the board she has heard from residents in the area who have concerns about a potential lot split.
“I’ve gotten questions about the fate of the house,” she said. “Most people I’ve talked with want to preserve the Gamble Rogers house because there are not many of them left.”
While splitting the lot does not guarantee that the home would be preserved, Tedrow said a potentially worse outcome could be on the horizon if a lot split is not granted.
Because of the size of the lot, a buyer could demolish the old home and would be entitled to build a new house as large as 56,000 square feet.
“The largest home in the city has a gross floor area of over 36,000 square feet — this 3.67-acre property is legally entitled to have a home 55% larger,” Tedrow told the Voice in an email. “To further put this into perspective, the city’s new library and event space total around 50,000 square feet. The home that could be built at 1020 Palmer Avenue under today’s Comprehensive Plan would be larger than both buildings combined on the city’s library campus and would dwarf every home in Winter Park.”
Such a house would also dwarf the home of Marc and Sharon Hagle, who spent years constructing the largest residence in Winter Park — the one Tedrow mentioned that is 36,000 square feet — just a few doors down Palmer Avenue.
“I think there are some buyers out there who might do that,” she told P&Z members. “I’m not that buyer. So maybe we flip this to somebody else …”
Owens, who also attended the meeting, said she appreciates that Tedrow came to Casa Feliz and is considering ways to find a buyer who might be willing to restore the home.
“We appreciate her willingness to work with us,” Owens said.
The property was most recently the home of Dr. Raymond Gilmer, an orthopedic surgeon who died in 2020 at age 90, and his wife, Sarah, who purchased it in 1977.
The home is now vacant and owned by the couple’s children. Tedrow said the family decided to keep the property off the historic register in case the land would be worth more with the potential for demolition.
A close-up of the front entrance to the property.
There is no publicly available list price because Tedrow offered a contract on the property before it hit the MLS.
She said the price of the existing house would depend on the exact configuration of a potential lot split, if approved, and other factors.
The house was featured as one of about a dozen properties in a 2004 book celebrating the architecture of Gamble Rogers in Winter Park by Patrick and Debra McClane.
“The initial series of interior spaces is unusual for a residence and more closely resembles a hotel or theater entry in that a lobby is provided, which is flanked by a coat room and a powder room,” reads the section on the property, referred to as the Plant House for its original owner. “Stepping up from the lobby, one then enters a large entrance hall nearly 45 feet in length. Triple arched openings on the south wall of the hall — with a fixed window in the center and double-leaf, multiplane doors on the sides — lead to the loggia and then the sunken patio, with Lake Osceola beyond.”
The house boasted features such as “floor buttons” in the dining areas that rang to wait staff in the kitchen, as well as “ornate wrought-iron railings and balusters [that] lined the staircase, and a velvet-covered handrail … provided on the interior wall.”
Jack Rogers, architect and son of Gamble Rogers, told the Voice last year that there are fewer than 10 true examples of his father’s work left in Winter Park as more are torn down every year.
“There’s probably 15 or 20 left, and eight or 10 are absolutely precious, and we seem to be losing them at the rate of one or two a year,” Rogers said. “We still have several wonderful examples.”
WinterParkVoiceEditor@gmail.com
Update: The original version of this story noted cannabis law as a part of Tedrow’s law practice. She no longer practices in that area.
A Century-Old Lifeline: Welbourne Preschool Endures Amid Loss of Black Landmarks
As change continues on Winter Park’s west side, a preschool that opened in 1927 continues to provide a heartbeat for the neighborhood
Nov. 24, 2025
By Beth Kassab
On Sundays, you can find the Rev. Ronald Critton preaching at Bethel Baptist Church, one of Winter Park’s oldest historically Black sanctuaries.
But more than 65 years ago, Critton started out just steps across Welbourne Avenue from his pulpit as one of the tiny voices on the playground of the Welbourne Nursery and Preschool, once known as the Winter Park Day Nursery Association for Colored Children.
“I do recall the merry-go-round,” Critton told a group gathered recently at a celebration of Welbourne’s history and a fundraiser for its future. “Back then, being a young Black kid, we weren’t allowed to be in certain environments, and that was the only school for us … I felt that I was loved and cared for.”
The Rev. Ronald Critton speaks at an event for the Welbourne Preschool.
On Winter Park’s west side — where old homes and buildings disappear almost as quickly as parking spots along Park Avenue at Christmastime — the Welbourne has remained a beating heart of the historically Black neighborhood for nearly 100 years.
This year, Hannibal Square, founded in 1881 by free Black families who worked for the city’s wealthy white winter residents, lost the Gardens at DePugh Nursing Center.
The first licensed facility for Black seniors, dating back to 1956, announced in September that it would close — the latest in a wave of redevelopment over the last two decades as land values have soared.
But the Welbourne, which opened in 1927, continues to buck the odds.
Artwork from Welbourne students was displayed at the event.
Executive Director Latonya Pelt said the school’s mission is too important to let go. She is grateful for a group of loyal supporters, including alumni like Critton, who have helped raise about $70,000 toward the school’s $100,000 goal. Local business leaders such as Gary Lambert of Gary Lambert Salon on Park Avenue and Rick Baldwin, founder of Baldwin-Fairchild Funeral Homes and Cemeteries and now operator of Baldwin Brothers Funeral & Cremation Society, were recognized among key supporters at the recent event.
“I tell our teachers all the time — we care beyond the classroom,” Pelt said. “We care if the children are hungry, if they need anything. We are all a village.”
A Welbourne student hands out pens to guests.
The Welbourne provides child care and preschool for free or on a sliding scale based on a family’s income. Full tuition for an infant is $315 per week and decreases to $170 per week for a 4-year-old.
The school currently serves 53 children, from infants to age 4 and is open Monday through Friday from 7 a.m. to 6 p.m.
The fundraising campaign helps provide reduced tuition for qualifying families and increase teacher salaries to reduce turnover. Payroll is the school’s biggest expense but also its greatest asset.
“It’s not a high-paying industry,” Pelt said. “We want to make sure we keep qualified teachers.”
Minnie Woodruff recounts her family’s story and her experience at the school.
Minnie Woodruff remembers one such teacher from when she attended Welbourne before graduating at age 4 in 1943.
Rick Baldwin talks with Mary Daniels, who once worked as a teacher at the school and later served as president of its board, and Mayor Sheila DeCiccio.
At the recent gathering, she recalled Mrs. Richardson, whom she described as “the teacher, the cook, and if you got sick she would blow your nose.”
Woodruff went on to attend Spelman College and graduate school and enjoyed a long career as an educator. She credits the preschool with helping lay a solid foundation for herself and her seven siblings in a segregated world.
That work continues today, though the school now draws families from a broader area than just Winter Park. Many parents choose Welbourne because they work in Winter Park or face long waiting lists for subsidized child care elsewhere.
“The average two-parent working family in the U.S. cannot afford high-quality childcare,” said Sharon Carnahan, who serves on Welbourne’s board of directors and recently retired from Rollins College as a psychology professor and executive director of the Hume House Child Development and Student Research Center.
Critton, the pastor at New Bethel, said he hopes more Welbourne graduates find their way back to supporting the school and the neighborhood, where he recently became a resident once again.
Upcoming Demolitions: At Racquet Club, a Gamble Rogers House and Park Ave Apartments
Two city advisory boards will consider the three projects this week
Oct. 7, 2025
By Beth Kassab
One of Winter Park’s most exclusive hang-outs wants permission to demolish a 5,400-square-foot two-story building at the front of its property and build a larger one-story structure to house a fitness center, locker rooms, tennis shop and offices.
The Planning & Zoning Board will consider the proposal Tuesday evening by the Winter Park Racquet Club, a private club that dates back to the early 1950s on Lake Maitland that offers swimming, dining, pickleball and tennis with initiation fees that run upwards of $22,500, according to one document that advertised a job posting there.
The changes at 2111 Via Tuscany have drawn criticism from neighbors on the residential street who say they are worried about commercial-like development, traffic and noise. As a result, the proposal has gone through revisions since the concept was tabled at the Sept. 2 Planning & Zoning Board meeting.
“The style will add cohesion to the rest of the club buildings, including the original clubhouse which was designed by [local architect James] Gamble Rogers,” read a description submitted by the club. “It will also mimic the aesthetics of neighboring homes, and the intent is for people driving by to assume that it is a residence that has been here all along.”
Residents expressed concerns about the disruptions to be caused by construction, light pollution, parking and other issues, according the minutes of a neighborhood meeting.
“I am extremely concerned that this project continues to seek to convert this house into a commercial multi-use facility,” Marci Greenberg, who lives across the street, wrote to the city, one of a number of emails received about the project. “With the new plans, there will still be a significant increase in traffic, parking in front of the building (as the new circular drive is 20 ft wide which is as wide as Via Tuscany) and an increase in noise. The current house, as such, contributes to the character and ambiance of the neighborhood. The proposed building looks commercial and detracts from our residential neighborhood.”
A sign in the neighborhood near the Racquet Club opposes changes there.
The club manager did not return a call for comment, but documents say the club is on a “membership waitlist” and is not accepting new members, meaning the project is not intended to allow any growth or expansion of services.
In response to concerns, the club has removed from the plans new parking that was to be added in front of the building and replaced it with a circular driveway.
City staff is also requesting other conditions such as the hours of operation remain the same, no new lighting be added and most exterior lights (other than for safety purposes) be turned off by 10 p.m.
Noise issues are also being addressed, according to the staff report.
“[The club] is proposing a six-foot acoustic sound barrier behind the eight-foot podocarpus hedge in front along Via Tuscany to screen the parking and buffer the noise concerns raised by the neighborhood,” it said. “This sound barrier will be the same barrier used to buffer the pickleball courts that is designed to reduce noise levels in outdoor settings and is made of a dense, soundproofing composite, and unlike a solid and rigid concrete wall, it both blocks and absorbs sounds more effectively.”
Another Gamble Rogers House Likely Gone
Not far from the Racquet Club is a secluded peninsula that stretches into Lake Maitland from its eastern shore called the Isle of Sicily — one of the city’s richest streets. James Gamble Rogers II, who also designed the racquet club, constructed the first home on the isle about 1930, an 1,800-square-foot French provincial home known as Four Winds that the famed architect lived in with his family until 1949.
Now the house at 3 Isle of Sicily is likely to be torn down as part of a plan to builder a larger home on the property.
A view of the home at 3 Isle of Sicily today as recorded by the Orange County Property Appraiser.
Over the years, the house was renovated extensively and now sits at more than 7,000-square feet.
Owners Kamran and Mina Khosravani, who acquired the property in 2011, are looking to build a new home that will top 10,400 square feet.
The home is not on the city’s historic register so the owners don’t need permission to demolish it, but will ask the P&Z Board today for approval of the new lakefront construction.
A rendering shows proposed new construction at 3 Isle of Sicily.
Jack Rogers, architect and son of Gamble Rogers, said he’s sorry to see the house come down, but it hasn’t looked like the original in decades.
“Unfortunately, the damage was done 50 or more years ago,” Rogers said. “The original house is completely gone.”
His father, who is also known for the Florida State Supreme Court Building in Tallahassee and the Olin Library on the Rollins College Campus, built about 50 houses in Winter Park, he said. His papers and plans are preserved at the Winter Park Library.
“There’s probably 15 or 20 left and eight or 10 are absolutely precious and we seem to be losing them at the rate of one or two a year,” Rogers said. “We still have several wonderful examples.”
Park Ave Apartments Face Demo for Townhomes and Synagogue
The apartment buildings dating back to 1922 known as El Cortez could be demolished to make way for new townhomes and a new synagogue if the Historic Preservation Board approves a proposal up for consideration on Wednesday.
The board tabled the request at its Sept. 10 meeting in order to see if the developer could save one of the three buildings at 210 E. Morse Blvd. that are part of the Interlachen Avenue Historic District. The property is also the last R-4 zoned land just off Park Avenue that has yet to be redeveloped.
The El Cortez Apartments along Morse Boulevard.
The city discourages demolition of so-called “contributing structures” to historic districts such as El Cortez, but does approve knock-downs when preservation isn’t feasible.
The property owner and applicant for the project, a company called El Cortez LTD and managed by AGPM founder Scott Zimmerman, said the buildings represent a “frame vernacular style,” but have been significantly altered over time with no original exterior materials or features remaining.
The new development would create townhomes on Morse and a synagogue along Knowles Avenue. Staff received 32 letters in support of the project and one against, according to documents related to the meeting.
In the 1920s the building were 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.”
Rogers said his dad told him he also stayed at El Cortez while Windsong, the Isle of Sicily property also likely set for demolition, was being constructed.
City staff is recommending approval of the project with the following conditions: A historic marker be placed there to commemorate the historical significance of the property and that the demolition not occur until the owner has a building permit from the city to ensure development plans don’t change between the time of the tear-down and new construction.
New Historic Survey Considered
The Historic Preservation Board will also on Wednesday consider a contract with Orlando-based KMF Architects for $75,000 to survey the city’s historic assets.
The proposal calls for updating the 2001 and 2013 surveys and will include an evaluation of Mid-Century Modern architecture (1950s-1970s), a era that hasn’t previously been surveyed citywide.
The work on Mid-Century Modern work will include a focus on Orwin Manor “to support the city’s consideration of a potential historic district designation.”
Four historic districts already exist in Winter Park — Downtown, College Quarter, Virginia Heights East and Interlachen Avenue — and those will be evaluated to determine if any non-contributing buildings now meet criteria for contributing status.
The survey will update records and remove properties on previous surveys that have since been demolished to produce a detailed report with photos that is both “informative and user-friendly,” according to the architects’ proposal.
New Park Avenue archway underscores historic Winter Park
A group of private donors combined with public dollars made the $400,000 project possible
Aug. 25, 2025
By Beth Kassab
Winter Park leaders on Monday celebrated the installation of the first of two archways that will bookend Park Avenue.
The $400,000 pair of signs emphasize the city’s commitment to historic preservation and were one of the last projects spearheaded by former Planning & Zoning Director Jeff Briggs before he retired at the start of the year.
Mayor Sheila DeCiccio gives remarks at an event to celebrate the new signs on Monday.
The City Commission provided about half the money for the arches made by Don Bell Signs and eight private donors covered the remainder.
Briggs has said the calls for donations were among the “easiest” he ever made with lots of enthusiasm for the markers that call even more attention to Winter Park’s popular dining and retail corridor, which was added to the National Register of Historic Places in 2011.
The sign on the north end stands at the intersection of Park and Webster avenues next to the public golf course known as the Winter Park Nine and in sight of historic home-turned-venue Casa Feliz.
The city seal now adorns City Hall as part of a refresh of the building over the summer.
A second arch on the south end near Park and Aloma avenues and just across the street from Rollins College is slated to go up at the end of September.
Private donors to the cause are: Rick Baldwin; Jim and Diana Barnes; Mike and Gail Winn; the Allan E. and Linda S. Keen Family; Larry and Joy Williams Private Foundation; Edyth Bush Charitable Foundation; Joe and Sarah Galloway Foundation and the Elizabeth Morse Genius Foundation.
The signs aren’t the only noticeable public upgrade along Park Avenue. City Hall, at the intersection of Lyman Avenue is sporting a new paint job with the city seal, featuring a peacock, now prominently displayed to passersby.
Winter Park city officials also said they were attempting to help Austin’s Coffee relocate and will try to negotiate a new lease with the Benefit Shop
May 15, 2025
By Beth Kassab
The City Commission approved changes to the historic preservation ordinance that are designed to discourage unapproved demolitions with clear potential consequences and to ensure homeowners don’t deviate from plans approved by the Historic Preservation Board.
Commissioners voted 4-1 to pass “Version 1” of the changes that say owners who knock down or dramatically alter historic structures without permission after going through the certificate of review process can be required to build the structure back exactly as it was, including using authentic exterior materials. In addition, they could lose any variances the historic board granted that allowed the project to move forward.
Commissioner Marty Sullivan was the only dissenting vote because, he said, he wanted “Version 2” of the proposed changes, which included the option of a financial penalty for such unauthorized demolitions capped at 30% of the building’s county assessed value — though Sullivan suggested the cap increase to 60%.
“I think 30% is way too little,” Sullivan said.
The debate over the ordinance, which had been delayed from earlier this year, centered on whether or not to include the monetary penalty, which drew fierce opposition from some in the city’s historic districts who viewed it as far too punitive.
But the version approved by the commission is potentially even more punitive when you consider the cost of losing variances on setbacks or other building rules.
Variances, or exceptions to the usual building code, are viewed as a clear benefit for historic owners to encourage them to preserve the outside architecture of buildings. For example, if the typical required buffer between a home addition and the property lot line is 20 feet, historic owners might be allowed to build to 10 feet.
As a result, losing those variances, as the ordinance says could happen in the case of an unauthorized demolition, is a “huge deal,” said John Skolfield, a builder who was elected earlier on Wednesday to serve as chairman of the Historic Preservation Board.
“If you think about the house in question that started all of this … we approved a beautiful design that brought it to 7,200 square feet,” he told the commission. “You have to build back without the variances, that’s a $500,000 to $800,000 ding.”
Last year, however, all but a small portion of the first floor and the chimney was torn down. The contractor agreed to pay $100,000 to make amends for the mistake and the project was allowed to go forward.
The episode set off a major debate and led to the ordinance changes.
Winter Park has about 400 historic structures including the College Quarter and Virginia Heights districts and individually designated homes and commercial buildings.
The historic board only has a say when it comes to major exterior alterations of buildings, not minor changes or repairs or interior projects. Window and door replacements or roof replacements, for example, are not required to come before the board so long as they stay consistent with the architectural style and must only follow the typical building permit process.
The new ordinance also requires additional checks on construction plans to make sure what the contractor does matches approvals given by the board. And it requires additional due diligence to make sure owners and contractors are aware earlier in the process if there is a part of the structure they won’t be able to save.
The city purchased the property rented by Austin’s and other businesses last year and the coffee shop has known for at least a year that the lease will end so that the city can use the property to add a turn lane on Fairbanks Avenue and make drainage improvements.
City Manager Randy Knight said the city has hired a broker to help Austin’s find a new location, will allow the owners to take anything from the property that they wish to take and will also return the security deposit.
But for Austin’s loyal supporters, that isn’t enough.
Speaker after speaker bashed the city for taking away a place that they said is considered a “sanctuary” by many in the arts community.
Mayor Sheila DeCiccio said she was frustrated by the misinformation she heard.
“We are not evicting Austin’s … they have had over a year to find a new space,” she said. “… We are paying a Realtor to help them.”
She explained that the intersection at Fairbanks and Denning is busy and accident prone and residents deserve a solution. They also deserve a fix, she said, to the drainage and flooding problems that occur in the area.
“Please take that into consideration when you criticize this commission,” she said.
Benefit Shop lease uncertain
The city is attempting to negotiate a new lease with the Benefit Shop, a thrift store that raises money for local charities by selling used household goods and clothes.
The group operated in City Hall for years but the space is now needed by city staff. The Benefit Shop is interested in moving to a small building at MLK Park where the city just spent $10,000 to fix the air-conditioning system.
But the Benefit Shop wants a lease that extends to 35 years with the city covering all major costs such as maintenance and insurance.
DeCiccio and other commissioners said that term was too long and could prohibit future commissions from additional uses of the building. The commission voted to attempt to negotiate a three-year lease for $1 each year at the Lake Island Park building. The Benefit Shop would be responsible for the insurance beginning in its second year.
A final deal, if reached, will come back to the commission for approval.
An unapproved demo, a $100k penalty and hours of debate
How a demolition in College Quarter led to proposed changes to Winter Park’s Historic Preservation rules, which will be up for a vote Wednesday by the City Commission
May 13, 2025
By Beth Kassab
A year ago, custom builder Charlie Clayton stood before the Historic Preservation Board and apologized, offering to make amends for the unauthorized demolition of a large portion of 965 Lakeview Drive, a 1936 home overlooking Lake Virginia in the College Quarter Historic District.
“I can’t take back what happened,” Clayton told the board on May 8, 2024. “… My interest is not to decimate the resources of the city … I’m not a guy who goes in and tries to destroy the town. I don’t get in trouble like this, but I’m in trouble now.”
Clayton said he even went door to door in College Quarter, one of the largest collections of near-century-old homes in the region, to explain how the second floor of the house was torn down, leaving just the chimney and a small portion of the first floor standing.
The board had only approved the demolition of a garage behind the house and the city ordered work to stop on the project when it learned of the demolition.
Clayton blamed miscommunication with his crew on the site and told the Historic Preservation Board he was prepared to pay $25,000 toward the city’s Historic Preservation Fund and complete the project in a way that would deliver the same end result — a new face on the front of the house that adds additional second-story windows and removes historically inaccurate columns added before the current historic preservation rules were in place.
A photo from the Orange County Property Appraiser shows how the home at 965 Lakeview Drive looked in 2023. The above image shows what the home looked like last year after demolition.
Ultimately, the historic preservation board and staff negotiated the payment to $100,000 and allowed the project to continue. Clayton paid the money the next day.
The board, though, could have issued what some preservationists argue would have been a harsher penalty: Require the homeowner and contractor to reconstruct the home exactly as it was and take back the building variances granted to the project that allowed the homeowner to add square footage to the home.
That choice — a financial penalty or a requirement to build back what was lost and lose valuable variances — will be at the center of the debate expected Wednesday when the City Commission considers proposed changes to the Historic Preservation ordinance touched off by what happened at the Lakeview house.
Commissioners will decide if they want the ordinance to explicitly offer the option of a payment (capped at 30% of the structure’s assessed value) in the event of an unauthorized demolition. Or if they will lean more heavily on the threat of removing variances and requiring reconstruction of an improperly demolished building.
The proposals follow a year of intense debate over the demolition and the historic preservation board’s response.
Ryan Phillips, who owns the home, recorded a conversation with a board member on the sidewalk in front of his house without the board member’s permission and used that to allege he was threatened and treated unfairly.
He spoke at multiple public meetings to allege impropriety over the city’s request that Clayton pay the penalty and lodged state ethics complaints against members of the historic preservation board, a city attorney and former Planning Director Jeff Briggs.
The Florida Commission on Ethics dismissed all eight of those complaints on April 30 because of a “lack of legal sufficiency.”
Phillips and Clayton did not respond to messages seeking comment for this story.
The variances Phillips was allowed to keep for his new construction after the demolition allowed for the home to grow from its original size.
Such variances are key perks for homeowners in historic districts, which enforce architectural standards for the exterior of homes.
Members of Winter Park’s Historic Preservation Board, along with city staff, say they have a job to do: maintain the historic character and authenticity of some 400 properties in the city’s resident-approved historic districts and individually-designated sites.
Their job is not, as retired Planning Director Jeff Briggs once put it, to be the “Historic Replica Board” — or one expected to sign off on every requested demolition or ignore violations of the city’s code. That would render the group a toothless overseer of new construction.
“Basically, it opens the door for everyone to ask for forgiveness and not permission,” Briggs said of violations that harm or destroy historic structures without the board’s approval.
And while the Lakeview house is a recent example of an unauthorized demolition. It’s not the only one.
At the historic preservation meeting last month member Lee Rambeau said changes to the ordinances are needed and she was in favor of adding explicit language about fines.
“I’ve seen a number of properties come before us and the final outcome did not look like what we approved,” she said.
Proposed changes to the ordinance also include stricter application requirements and add a “pre-application” review by the board so that property owners can receive early design feedback before spending a lot of money on detailed renderings. The changes also would require property owners to give more detailed information about the materials they will use and architectural elements.
The change also attempts to cut down on unexpected requests for demolitions after a project starts by requiring applicants to submit a “due diligence assessment” identifying all proposed demolitions or alterations in advance.
A number of historic property owners, including Clayton, spoke out at a community meeting earlier this year against including fines as part of the proposed changes.
At the Historic Preservation meeting in April the board ultimately voted to recommend the version of the ordinance without the fines.
Aimee Spencer, who recently rotated off the board, said that version is potentially harsher on homeowners.
In the case of the Lakeview house, she said, the board attempted to “exercise empathy and kindness” and not penalize the homeowner for work done by the contractor without his knowledge. The project was allowed to proceed as planned rather than have its variances revoked.
But the case became one of what she saw as a “sore winner,” she said.
Wade Miller, who until last month served as board chairman, also said he saw the rebuild requirement and loss of variances as a harsher penalty.
But members of the public and board members spoke against including the fines in the ordinance.
“If that is what I am hearing from the community and members of the board, then so be it,” he said. “… we will see how that plays out … and I think it ultimately will become a much more severe outcome in the future for homeowners of historic properties.”
Betsy Owens, executive director of Casa Feliz, one of Winter Park’s most prominent preservation stories, said a fine could be viewed by some property owners as a cost of doing business rather than a preservation incentive. A requirement to rebuild a demolished structure is considered a best practice in other cities that also value historic preservation such as Coral Gables or Charleston, she said.
“I think the best way to make things right is to have you rebuild what you knocked down,” she said. “Losing variances is a stronger disincentive than a fine.”
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