Neighborhood battles squatters in Winter Park

WINTER PARK, Fla. — Walk down Fifeshire Drive in east Winter Park at any time of the day, and you’ll see children playing in the road, on expansive lawns, or in self-built “tree houses” perched high above the ground.

Their parents take pride in where they live and closely look out for each other’s families.

Multiple people poked their heads outside not five minutes after the news camera arrived in the neighborhood Wednesday.

They were glad, they said, to finally shine a light on the reason they were more and more fearful of allowing their kids to play in the street: one of the homes had been occupied by squatters since June, creating a tense – and ever-escalating – atmosphere.


“It’s been a nightmare,” Justin Mielcarek said.

Back in June, Mielcarek and other neighbors noticed the house at 2441 Fifeshire Drive appeared to be occupied after six months of vacancy, with a car in the driveway, trash bags in the bins, and coverings put over all the windows.

When they called the property management company that operates the house to find out who their new neighbors were, they said the company representatives had no records of any tenants.

Police were called and raided the home, neighbors said. They remembered seeing some people jumping out of windows and over fences. One man wound up in a pool.

“K9 units, helicopters. Gentlemen running, police officers chasing after them,” one neighbor, who identified herself as Leslie, described.

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Leslie and others said someone produced a fake lease, and officers left. That was just the beginning.

In the weeks since Winter Park officers have been called to the home 14 times. Now, they constantly patrol, stop the occupants, and – while looking for probable cause to make an arrest – try to keep the peace.

Neighbors complain about cars coming and going at all hours of the night, headlights shining into bedroom windows, and speeding through the neighborhood during the day.

“On one occasion, a few days ago, [one of the occupants] almost hit one of my children,” Christine Armstrong said.

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Simultaneously, the homeowner, who lives out of the country, filed a lawsuit seeking to evict the squatters. Neighbors blame her for allowing them to move in. They said the home hasn’t been cared for a while, and despite friends of theirs offering to buy the property, she’s refused to sell, leaving the home empty between paying tenants.

“We have three rental properties on the street alone, and it’s very evident which they are because they’re not kept up,” Armstrong said.

WFTV contacted the attorney representing the property owner, who said a judge signed a final judgment against the squatters on Tuesday. Once it appeared in the docket, he would be able to apply for a writ of possession to give to Orange County Sheriff’s deputies.

Three of the people who lived in the home said they too were victims. They said a cousin first entered the home and then invited them to stay there. They claimed they gave the cousin money, and he promptly disappeared.

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When asked why they hadn’t tried to lawfully rent the property through the actual owner, they said they were looking to move out due to the hostilities in the community, which they attributed to racism, an accusation the neighbors denied.

Real Estate Attorney Mark Lippman said many of the squatters he encounters are victims of a scam, though he was not involved in the Fifeshire Drive dispute. He said websites like Facebook Marketplace are a breeding ground for rental scams and urged would-be renters to beware of those listings.

While the neighbors requested stricter code enforcement on the rental properties to force the owners to take care of them, Lippman said Winter Park’s was one of the more aggressive units in Central Florida, although it was understaffed like many other communities.

“I think we need to figure out something,” Mielcarek said. “The cops are handcuffed because they can’t do anything… and the court process takes however long it takes. You wish it was a little bit of a faster process.”

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