Backyard Palm Trees on Lake Spark a Pricey Legal Battle in Winter Park
A homeowner is suing the city over a decision that the height of his landscaping must be limited to help maintain the lake view of his neighbors
Nov. 12, 2025
By Gabrielle Russon
A fight over two palm trees has cost the city of Winter Park nearly $29,000 in legal fees so far.
Jonathan Cole, the owner of a newly constructed 5,300-square-foot home at 721 Virginia Dr., filed a legal challenge to keep a pair of backyard palm trees that his neighbors say impede their view of Lake Virginia.
Cole is asking Orange Circuit Court to overturn a decision by the city — and a construction condition Cole originally agreed to — that limits landscaping behind his house to less than six feet in height.
Winter Park spokeswoman Clarissa Howard said in a statement, “The case has been fully briefed and is in the hands of the three-judge panel for a ruling. We have been given no indication as to when that ruling might be issued.” She said no settlement talks are currently underway.
Cole’s attorneys did not respond to a request for comment for this story.
Cole argued he should be allowed to keep his trees since his interpretation of the Planning & Zoning Board’s decision is that the height limit doesn’t apply to his entire backyard, only the property line.
“This is a case of local government overreach and cries out for reversal,” he said in his February court petition. “Almost every single home on Lake Virginia has either very large trees on or near its property line running down to the lake or very large privacy hedges — and this includes the eastern neighbor who’s the one that complained about this.”
The tall, skinny palm trees don’t ruin anyone’s view, Cole’s legal team said when the issue went before the Winter Park City Commission in January. But several city officials said they were concerned about setting a precedent to allow the palm trees and unanimously voted to uphold the P&Z Board’s 2021 decision. Cole then filed a circuit court challenge.
Winter Park officials said the six-foot limit is reasonable to protect his neighbors, and Cole had been given more than his fair due process.
With the approval of P&Z, Cole “got everything that he asked for (all the square footage, construction closer to the lake, all the coverage of property, etc.) but was merely required to be considerate of his neighbors by restricting the height of the landscaping behind his home to no more than six feet,” the city said in an August court filing in response to Cole’s complaint, which is part of the hundreds of pages of court records.
The city also pointed out that Cole and his attorney both agreed to the six-foot requirement at the time in 2021. Cole missed the 30-day window to challenge the P&Z decision.
Construction was delayed on Cole’s house, and the lakefront landscaping was finally installed last year. That’s when his neighbor alerted the city about the two palm trees and overgrown holly shrubs.
Cole maintained he was in compliance, while the city called the plantings a violation of the original agreement.
Both Cole and his neighbors made emotional arguments to the City Commission earlier this year.
Neighbor Michelle Randolph said Cole already received special permission to build his home and now he wanted more.
“He was granted a major privilege to be able to build a house of this size and to be able to shift the house against the code … towards the lake,” Randolph told commissioners in January, according to court records. “This is what we were given as residents — just the common courtesy of please don’t plant anything over six feet. Like, you’re getting the house you want. You get to move it towards the lake. Please don’t plant anything over six feet.”
She insisted the palm trees did affect her lake view — even more so because of the house’s ultimate location.
Cole said he was exhausted by the construction process and has worked to satisfy his neighbors.
“Clearly I’m being painted as this guy that’s built a privileged monstrosity,” he told city leaders. “I’ve tried to be neighborly. I’ve tried to have discussions.”
When construction started, his daughter was 12; now she is 16, he said. Cole bought the vacant lot in 2020 for $2.1 million, according to Orange County Property Appraiser records. The property’s value was assessed at about $3.8 million this year.
“I’m sick of dealing with the stress of building a house,” Cole said. “At this stage, I want to be done with it. I don’t have time to fight this forever. I’m shocked that I’m here talking about palm trees.”
WinterParkVoiceEditor@gmail.com
Shocking that violating an agreement stresses the party that breached it.
Amen. So typical.
Mr. Cole, interesting the trees were placed at the edges of the lot, yet none in the center (where it looks so empty). Might that have obstructed your lake view? IMHO as a WP taxpayer (I know you didn’t ask for it) just save us all the legal fees and take them down. You could donate them to a city park or museum and take a tax deduction. Your neighbors might in fact be annoying, even hypocritical “Karens” , but these trees are stressing you out and worse yet, they aren’t bringing any beauty to your lot. They look like a giant game of lawn darts where nobody got close to the bullseye in the center of your lot. Call in a worthy landscape architect who can create amazing gardens from specimens all coming in at under 6 ft tall.
Good idea. The park with the bus station seats by the bakery on Orange Ave could use some trees.
Here’s an idea.
Mr. Cole apologizes to his neighbor, apologizes to the city, pays the city the $29k it spent, and expresses his desire for a harmonious relationship with his neighbors and the city.
Too simple for today’s litigious environment.