Florida homeowners face property liens after major roofing group collapses into “insolvency”

NAPLES, Fla. (WINK) — Dozens of Southwest Florida homeowners are facing a double blow of unfinished construction and mounting debt after the sudden financial collapse of Kelly Roofing, a long-standing Collier County contractor. 

The collapse has left customers dealing with bounced refund checks for paid deposits, abandoned job sites in the middle of peak hurricane season, and secondary legal demands from a material supplier seeking payment directly from property owners.

For decades, Kelly Roofing operated as a family-owned staple in Naples. However, after transitioning ownership to private equity firm Monument Microcap Partners a few years ago, the business became part of a wide spread portfolio. The equity firm absorbed multiple regional contractors, including Integrity Roofing and Gutters in Central Florida and Reliant Roofing near Jacksonville.

Trouble surfaced two weeks ago as WINK Investigates first broke that Kelly Roofing had declared insolvency. Homeowners who had paid initial deposits reported receiving refund checks that bounced due to frozen accounts.

Bill Rakow, a U.S. Marine Corps veteran and retired construction professional living in Naples with his wife Nancy, gave the company over $29,000 upfront in May—representing 75% of his project's total cost. Shortly after workers removed tiles from his roof, communication stopped, leaving his home vulnerable to summer rains.

Nancy showed Chief WINK Investigates Reporter Chorus Nylander multiple leaks in their home.

"We were quite frankly shocked," Rakow said. "Because they've already started the work and it's been raining real hard, we've got a couple of small leaks. I feel bad... I feel angry."

Material Suppliers File Liens Against Homeowners

The crisis worsened when the main supplier for Kelly Roofing, ABC Supply Company, looked to the homeowners to recoup unpaid bills. Under Florida mechanics' lien laws, if a general contractor fails to pay a supplier for materials delivered to a site, the supplier holds the legal right to place a lien against the homeowner's property—even if the homeowner paid the contractor in full.

ABC Supply Company has filed construction liens against at least two dozen impacted homeowners.

WINK Investigates spoke with John Watson of Naples. He paid $65,000 to Kelly Roofing for a project completed in June, only to receive a subsequent lien from ABC Supply for over $25,000.

“I’m in my 90th year, I have never received a lien on any property I’ve owned. This was a complete surprise,” Watson said. 

We also interviewed Barry Stivers from North Naples. He handed over a $9,600 deposit in May. He had materials delivered to his home but work never started. He also has a lien now on his home. 

"I'm the victim, and I'm being charged all the money. It's an amazing, horrible situation that we're in,” Stivers said. 

"Instead of going after me first, ABC should be going after Kelly," Rakow said.

Corporate Disputes and Legal Fallout

Court records reveal that the failure coincides with ongoing litigation spanning Delaware and Florida courts. Kelly Roofing's management structure has accused the founder of Integrity Roofing & Gutters, Chantelle Flores, of multi-million dollar fraud following their merger last year.

Flores' legal counsel denied the allegations; they've filed counter claims.

In a statement to WINK Investigates they said, "She is determined to get to the bottom of what happened. She intends to pursue every dollar she and her customers are owed. You cannot take control of a company, cannibalize its value, and then walk away when the bills come due."

Attempts to reach Monument Microcap Partners, Integrity Roofing & Gutters, and ABC Supply Company for official comment were not returned.

Kelly Roofing has sent multiple emails to its customers, now claiming the legal battle played a role in the financial reality of the overall company. 

Former Owner Steps In Amid Industry Risks

Late Friday, impacted customers received an email update announcing that former owner Ken Kelly had repurchased the company with plans to resume operations and complete unfinished jobs.

While some residents are waiting to see if the buyout resolves the outstanding supplier liens, others cannot afford to wait during active storm season. Local contractor Mighty Fine Roofing stepped in to finish the Rakow’s roof at cost, waiving its profit margin to seal the open structure.

Industry experts warn the broader fallout could impact insurance coverage across the region. 

David Kronk, owner of Evolve Insurance in Venice, noted that homeowners who used insurance payouts for their initial down payments may lack the funds to pay a second contractor, potentially leaving properties unfinished and opening the door for the homeowners to lose their insurance coverage.

"So it could leave people with unfinished roofs that are then uninsured,” Kronk said.

Ken Kelly told Chorus Nylander he is now trying to get insurance and all the legal documents necessary to acquire Kelly Roofing. He is scheduled to do an interview with Nylander on Tuesday.

WINK Investigates will keep you updated on what his plans are and any updates on these customers' circumstances.

If you have a story you'd like WINK Investigates to look into email us at winkinvestigates@winknews.com or call our tip line at 239-344-5074.