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.

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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