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Real estate agent pleads guilty to $11M embezzlement

Stephen Webster is taken into custody

Stephen Webster is taken into custody on April 1, 2026, to start his state prison sentence, in Plymouth Superior Court in Brockton. (USA TODAY Network via Reuters)

Real estate agent pleads guilty to $11M embezzlement

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The former owner of a South Shore real estate firm has pleaded guilty to and other financial crimes and has been sentenced.

The embezzlement led to agents losing commission checks and homeowners and buyers losing money held in escrow accounts during pending transactions, according to the prosecution.

Stephen Webster, 63, principal of Success Real Estate until it abruptly folded in December 2024, appeared on April 1 in Brockton , where he pleaded guilty to felony counts of embezzlement, larceny, misleading police and publishing a false financial statement.

With offices in Marshfield and Braintree, the real estate broker had approximately 140 agents.

A restitution hearing will be held after Webster’s release to determine how much Webster will be ordered to pay his victims, many of whom were present in the courthouse or via Zoom for the change of plea and sentencing.

Judge Daniel O’Shea handed Webster a two-to-three-year sentence in state prison, followed by a five-year probationary period during which Webster cannot hold positions of fiduciary responsibility without prior consent of the court.

Assistant District Attorney Alex Zane had asked for a six-to-eight year sentence, arguing that Webster abused the trust on which the real estate business depends.

“(Webster) used trust as a means to steal,” Zane said. “He weaponized trust at the exact moment when people are financially exposed.”

Webster’s statement after sentencing

“I’m profoundly sorry,” Webster told the court. “I’ve twisted myself into a pretzel trying to keep this from happening.”

Webster described his victims as friends and colleagues, saying his crimes stemmed not from greed, but from a series of bad business decisions which would put his company under constant stress.


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“My biggest regret is not being able to repay them because I’m going to prison,” he said. “Now they have to wait even longer for that money.”

Webster said that upon release from prison, he will build a new business and compensate his victims.

“I don’t know how or what,” Webster said. “But I’m going to work night and day until they’re paid back and made whole.”

‘He preyed on us all’: Victim statements

Mark Ryder said he worked for Webster as a real estate agent and electrician. Webster solicited loans which he never paid back, leaving Ryder and his wife to absorb a $75,000 loss, he told the court.

That included money his wife had saved up toward a comfortable retirement, Ryder said.

“Now that dream is shattered,” he said.

Jennifer Kern was also an agent for Success Real Estate. She told the court that Webster not only harmed agents by stealing commissions, but caused lasting harm by damaging their professional reputations.

“We’re connected to Webster,” she said. “It will be difficult moving forward.”

Stacy Ballerino told reporters after the hearing that Webster owes her just over $400,000.

“He preyed on us all,” Ballerino said.

Ballerino said Webster’s crimes were motivated by an extravagant lifestyle, not poor business decisions, and cast doubt on Webster’s stated intention of paying people back.

“He’s not paid back a single person I know a single dollar,” Ballerino said.

In a victim impact statement Ballerino provided to The Patriot Ledger, she elaborates on Webster’s lifestyle, claiming he spent sums on vacations to Hawaii and Montana, luxury vehicles, a $10,000-per-month condo in Boca Raton, Florida, and stays at the Encore casino.

Webster’s business operations required minimal expenses in terms of staff and office space, Ballerino said in her statement.

“There was nothing for him to do except make money off each one of us,” she wrote. “Instead, he stole what was never his.”

Carolyn Glynn, another former Success agent, agreed.

“It was his lifestyle,” she said. “He was living the lifestyle of the rich and famous on our dime.”

The failure of Success Real Estate

Webster diverted more than $11 million from escrow accounts he controlled as principal of Success Real Estate over a period of two years before his business folded abruptly in November 2024, according to the court documents.

He used the money to prop up his business, meet personal debts and discretionary expenditures, including luxuries, Zane wrote in his summary of the case.

Of the $11 million in diverted escrow funds, a smaller portion ‒ $584,000 ‒ remains unaccounted for, according to Zane’s sentencing recommendation.

Reporting by Peter Blandino, The Patriot Ledger / The Patriot Ledger

USA TODAY Network via Reuters Connect

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