With more than $2.6 million in unpaid taxes on the books, portions of which have gone unpaid for many years, Wilton is reconsidering a new approach to collecting its money.
Wilton’s Manager of Assessing and Tax Collection Hollie Rapp is once again recommending to the Board of Selectmen that the town hold a tax sale, which could potentially generate over $1.5 million in back taxes in a short time.
“This method is not only effective, but also incurs no cost to the Town, as all fees are covered by the sale itself,” Rapp wrote in a memo to the BOS on July 29.
On Tuesday, Sept. 2, the BOS heard more details from Rapp and Adam Cohen, an attorney with Pullman & Comley whom Rapp recommended and who said he works with numerous Connecticut municipalities organizing tax sales.
Selectman Josh Cole, who was not in attendance at Tuesday’s meeting, is also employed by the large Bridgeport-based firm to which Cohen belongs.
Taking into account both residential and commercial categories, the total amount of delinquent tax in Wilton, including fees, as of Sept. 2, 2025, is $2,645,319.84. By putting her suggested criteria into play for a tax sale, Rapp said on July 29 that the town could potentially recoup $1,588,614.54, as well as $11,469.88 in delinquent sewer-usage fees.
A spreadsheet of properties that would be targeted totals 25, both commercial and residential, for a grand total of $2,042,574.26 including taxes, collection and attorney fees and interest. Seven of these owe more than $100,000 in total, with two of them topping $250,000.
“In my personal experience, tax sales are extremely, extremely effective,” Town Administrator Matt Knickerbocker said.
Cohen, who said he has done tax sales for about two-thirds of the towns in Connecticut, explained that the process is much like a foreclosure on a property, but is a simpler, much faster and a less-costly process from the town’s standpoint in terms of legal costs and fees.
“Technically, a tax sale is a foreclosure,” he said. “It’s a non-judicial foreclosure.”
Cohen said that, after being alerted by the town that there is going to be a tax sale, many property owners will just immediately pay up their back taxes.
“I would say that roughly half of all the demand letters that I send out get paid in full … so it can be very effective to just cut that number in half right there,” he said.
“A letter on a lawyer’s letterhead tends to be just a little more persuasive,” Cohen said, rather than requests that are sent by the tax collector.
After that, he said, research is done on the property, with a series of notices given to the property owners by return-receipt mail. At this phase, Cohen said, an additional quantity of people will respond with payments in order to avoid having their properties auctioned off.
Based on information that she garnered from other area municipalities about their experiences holding tax sales, Rapp suggested that Wilton make the tax sale criteria be people who have been delinquent for three years or more, and/or anyone who owes $25,000 or more in taxes.
“This approach ensures equitable treatment of all taxpayers,” Rapp told the BOS, “and aims to address significant delinquencies effectively.”
Cohen said other town offer go after even small delinquencies.
“Three years is pretty standard,” he said. “$25,000 is pretty high. I usually see a lower number, like $10,000.”
Cohen stressed, however, that the town could handle it any way it wanted, as long as it was a fair criteria for everyone. He also emphasized that once people are put on the notification list, they should not be removed as it wouldn’t be fair to others, so the town needed to be clear on what the criteria were.
“To be perfectly frank, it almost doesn’t matter what your criteria are as long as you stick to it,” he said.
“Shame List” or Necessary
BOS members, meanwhile, expressed some trepidation about the process overall, referring to the list of delinquent residents as a “Shame List.”
“For me, it’s really about the shame,” Selectwoman Kim Healy said. “I really feel very uncomfortable.”
First Selectman Toni Boucher noted that the tax records are already public.
“It’s out there already,” she said, reminding the BOS that Rapp has broached the idea of doing a tax sale last year, but the BOS had not pursued the idea.
Selectman Ross Tartell raised the question of what the town was actively doing to help people who may be in financial straits.
“If somebody is financially strapped … What sort of things can we do?” he said.
“I’m very uncomfortable with this but I’m also understanding that it’s very necessary,” Tartell said.
Healy suggested that they might want to consider just doing the delinquent commercial properties first, which Cohen said was possible.
“Most of these are not commercial,” Rapp pointed out.
Boucher said that some of the properties have been delinquent for 14 years.
“Fourteen years. How much more time do you want to give someone after 14 years, or 10,” she said.
The BOS chose to wait and get more information, if possible, from neighbor Ridgefield about their experience with tax sales.
The town of Wilton must be run as a business. Delinquencies are a problem all businesses must address. As pointed out by the attorneys, not everyone must be included in an initial filing. For those concerned about shaming people, then only go after those that have not paid for 5 years or more, and who owe more than $25,000. I would make that public and let people know that this is the first round. Maybe then other delinquents will pay up before a second round occurs.