The $35 million estate of Bradley H. Jack, the former Lehman Brothers Holdings Inc. managing director who was arrested twice for allegedly forging drug prescriptions, may be sold at a municipal auction in Fairfield after he failed to pay property taxes dating back to July.

Jack, 53, was charged Friday by Westport police with second-degree forgery in connection with an incident last November when he is said to have forged the date of a prescription for a controlled substance at a CVS pharmacy that was made out to him by a Fairfield doctor.

On the same day that Jack turned himself in, Fairfield placed his compound at Sasco Point on a list of delinquent homes to be included in a tax sale within the next four months, according to town tax collector Stanley Gorzelany. The sale date hasn't been set.

"We had been discussing a tax sale for weeks before that happened," Gorzelany said of Jack's most recent arrest. "It was just pure coincidence."

Jack, a Westport resident, and his ex-wife Karin are listed as owners of the 20-acre waterfront estate in Fairfield, the residential property with the highest value in town. The estate, at 1143 Sasco Hill Road, is appraised at $34.5 million -- and with an assessed value of $24.5 million for property-tax purposes -- and boasts five buildings, an in-ground pool, tennis courts and a stable.

According to a list of tax-delinquent property released in February by the Fairfield Tax Collector's Office, the Jacks' unpaid tax total was also the largest -- $271,923 owed on the estate dating to 2010. The total annual tax bill is $543,847.48.

Jack, who posted $5,000 bond and is scheduled to appear March 21 in Norwalk Superior Court, bought the property in 2001 for $24.45 million, according to the Fairfield Assessor's office.

Individuals who owe more than $50,000 in back taxes, regardless of how long they've been delinquent, will have their property subject to a tax lien sale, Gorzelany said, citing criteria set by the town of Fairfield.

If Jack doesn't pay the back taxes before the auction date, buyers will have the opportunity to acquire his property at a starting bid of $426,240 and unspecified legal fees associated with the sale, Gorzelany said. The starting bid includes quarterly taxes that will be due in April.

After a tax sale, delinquent taxpayers have six months to redeem their property by paying the back taxes to the town and paying the winning bidder up to 9 percent of their final bid, Gorzelany said.

Last June, Jack was charged with second-degree forgery and forgery of prescription after Fairfield police said he tried to illegally obtain Oxycontin and Ritalin pills at a local CVS pharmacy.

In August, he was granted permission in Bridgeport Superior Court to enter the accelerated rehabilitation program, which if successfully completed, would allow him to avoid prosecution on the drug charges.

Jack had received treatment for cancer, had had a valid prescription in the past and had no prior criminal record, his attorney, Robert G. Golger, said in court in August. Golger didn't immediately return a call on Tuesday seeking comment on the tax sale.

Jack joined New York-based Lehman in 1984 and ran investment banking from 1996 to 2002, when he became co-chief operating officer with Joseph Gregory. In 2004, he was named to the office of the chairman with the responsibility of overseeing all of the firm's investment banking relationships.

He decided to retire from New York-based Lehman to pursue work in the nonprofit sector and spend time with his family, Richard Fuld, Lehman's chief executive officer at the time, said in June 2005. The company went bankrupt in September 2008.

Bloomberg News and the Westport News contributed to this report