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Prairie Grove residents facing bills in thousands for new roofs – but ask why HOA isn’t paying

Residents say their monthly HOA costs should cover expense

Contractors work on a roof of a Cobblestone Woods townhome on Aug. 20, 2025 in Prairie Grove.

Residents of a townhome community in Prairie Grove said they shouldn’t be on the hook for the cost of new roofs, arguing that it’s up to their homeowners association to finance the project.

Cobblestone Woods in Prairie Grove, just north of Crystal Lake, is a townhouse community with 170 units that was built in the early 2000s. With most of its roofs now reaching 20 years in age, the HOA is looking to issue a special assessment to replace all the roofs and decks at a cost of an estimated $2.3 million – and is asking residents to cover the costs on top of their monthly HOA fees.

Some residents are pushing back, citing their HOA rules and regulations that it is the HOA’s responsibility to replace the roofs and decks, rather than the residents’.

However, according to Cobblestone Woods’ articles of incorporation document, the board may levy a special assessment to make “major repairs, additions, alterations or improvements” to common areas, and “each owner shall be responsible for the payment of the amount of the special assessment.”

But 12-year resident Craig Brandon Steele questions whether the HOA has properly managed its funds and is now relying on residents to pick up the pieces.

The entrance of the Cobblestone Woods townhome community in Prairie Grove.

The Cobblestone Woods HOA fund dropped to $0 in 2022, Steele said. He said he’d gotten explanations that expenditures over the years were more than what the HOA was bringing in. But he still questions spending transparency.

“Somehow, there was money in the fund, but all of a sudden it disappeared,” he said.

Steele was elected board vice president in June. Before that, Steele filed a petition citing an Illinois Common Interest Community Association Act provision stating that, if the combined regular and special assessments for the current year exceed 115% of the previous year’s total, unit owners have the right to challenge the assessment. Over 30 homeowners signed on to the effort, but residents failed to reverse the assessment in a vote held during the HOA’s July meeting.

“We all know the roofs are going to need to be done,” he said. “We just want to make sure there is transparency, and maybe there is a better way to do it without such a big cost to the community.”

Assessment payments are set to start Sept. 1. Depending on the unit type, residents may be subject to pay somewhere between $11,000 and $15,000 for the estimated $2.3 million assessment, Steele said.

“You can’t threaten people and say you just have to pay this,” he said.

A possibility that led to funds dwindling is the fact fees were not increased for almost 10 years, Steele said. More recently, the HOA fees were raised the maximum 15% this year and last year.

Steele was hoping to move to North Carolina, but he said the outstanding special assessment sent buyers away.

“I’ve already lost money in this scenario,” he said.

Steele and other neighbors are sharing concerns over the lack of transparency in the HOA, saying few details were shared about the roof bids and that the board recently picked a new property management company without a vote.

The HOA transitioned to a new property management company, Westward360, in March because of concerns over the previous company, residents said.

Representatives from Westward360 did not return requests for comment. Other HOA members could not be reached for comment or declined to comment.

“I’m trying to stand up for the community because no one has this money to pay for these things,” Steele said.

Michelle Meyer

Michelle is a reporter for the Northwest Herald that covers Crystal Lake, Cary, Lakewood, Prairie Grove, Fox River Grove and McHenry County College