Success Real Estate Founder Pleads Guilty to Embezzlement

Despite its name, the Boston-based brokerage Success Real Estate failed and now its founder is headed to prison after pleading guilty to embezzling from escrow funds.

Stephen Webster changed his plea in court on Wednesday, facing charges of embezzlement, witness intimidation and publishing a false financial statement. The 67-year-old real estate agent was sentenced to two to three years in prison, WCVB reported, followed by five years of probation.

Webster will also need to pay restitution to his victims, though the amount for that has yet to be set.

Prosecutors indicted Webster in mid-September. He was arrested nearly three weeks later in Florida and brought back to Massachusetts.

Webster embezzled $11 million from client escrow accounts, according to prosecutors, who claimed Webster used stolen funds on “credit card payments, payroll, gambling and personal expenses.” Webster’s attorney previously said the brokerage founder was moving money around “trying to cover to make ends meet.”

“I am profoundly sorry to everybody in this court and everybody online,” Webster said in court. “I twisted myself into a pretzel trying to stop this all this time.”

Several agents who worked at Success bemoaned what they perceived as a lenient sentence, claiming Webster cost them and their clients thousands of dollars and destroyed reputations. One former agent of the firm said she had $400,000 stolen by Webster, including $320,000 on a single deal.

Webster announced Success’ closure in December 2024, leading the company’s website and Facebook page to promptly disappear. When agents went to deposit their commission earnings, checks bounced, according to plaintiffs in multiple lawsuits.

More than a year ago, at least 13 agents filed lawsuits against Success and Webster, civil litigation that remains ongoing. Seven real estate agents claim they are owed more than $100,000 for bounced commission checks.

Success claimed to transact more than $1 billion in sales over its last five years of operation. It was in business for 32 years.

— Holden Walter-Warner