A Massachusetts broker-owner has pleaded guilty to embezzling $11 million from escrow accounts and was sentenced to up to three years in prison, followed by five years of probation.
Success! Real Estate broker-owner Stephen Webster was initially indicted in September 2025 and was arrested in Palm Beach County, Florida, later that month. The investigation began when Webster submitted a falsified bank letter during the course of an audit that stated he had $1 million in an escrow account. According to a report from Boston.com, regulators subsequently found that the account held just over $7,000.
“I am profoundly sorry to everybody in this court and everybody online. I twisted myself into a pretzel trying to stop this all this time,” Webster told the court during his plea hearing.
Webster abruptly closed Success! Real Estate in December 2024 and moved to Florida. Last year, more than a dozen agents of the brokerage sued for unpaid commissions totaling nearly $500,000.
According to Boston 25 News, Webster used the embezzled funds “to pay high-interest loans, gambling withdrawals, personal debt, and luxury expenses, including BMW and Tesla vehicles, as well as rentals in Florida.” However, in his statement to the court, Webster said that the luxury purchases were not the point.
“This was not about greed. This was not about me stealing money or taking money. I got into a situation I couldn’t get myself out of,” Webster told the court.
Former Success! agent Stacey Ballerino told Boston’s WCVB she does not believe the punishment fits the crime in this case. “I’m disgusted. I’m disgusted with this. Someone goes to jail for two years and steals, I mean, dozens of people’s savings. He preyed on all of us. And all of us respected him. He’s a scumbag,” Ballerino said.
