A Massachusetts judge has sentenced a South Shore real estate broker who diverted $11 million in escrow funds for personal expenses to up to three years in prison, half of the prosecution’s request.
Stephen Webster, 63, pleaded guilty to causing the downfall of Success! Real Estate, Inc., a company that abruptly shut down in December 2024 amid an embezzlement investigation.
Plymouth Superior Judge Daniel O’Shea sentenced Webster to two to three years in state prison, followed by five years of probation.
Conditions of Webster’s probation include the former longtime broker and principal not being able to hold a position of fiduciary responsibility without prior court approval and being ordered to pay restitution.
The Commonwealth recommended that Webster be sentenced to six to eight years in prison.
Webster’s sentencing is not sitting well with his longtime employees, including Stacy Bellerino, who told reporters that her former boss owes her over $400,000.
“I’m disgusted that someone goes to jail for 2 years after stealing dozens of people’s savings,” Ballerino said after the sentencing hearing on Wednesday. “You can do all that and lie to everyone and only get two years? Must be nice.”
Investigators discovered a “sweeping pattern of financial misconduct” when reviewing Webster’s South Shore Bank and Rockland Trust records, accounting ledgers, and witness interviews, the Plymouth DA’s Office stated in a release.
The investigation determined that Webster transferred roughly $11 million from designated escrow accounts and into his personal and business accounts. Webster used those heaping funds to pay credit card debt, business loans, and personal expenses, including monthly rent of $10,000, and gambling-related expenditures in Massachusetts and Florida.
“Stephen Webster treated client escrow money like it was his own personal bankroll,” Plymouth District Attorney Tim Cruz said in a statement. “He did not just steal money — he shattered trust, destabilized transactions, and left hardworking people to deal with the fallout.”
“This sentence holds him accountable for a scheme that caused real financial and personal harm,” the DA added.
In March 2023, Webster omitted one escrow account entirely and submitted false financial documentation to the state Department of Licensure after the agency notified the businessman of a pending audit, according to prosecutors.
Webster pleaded guilty to embezzlement by a fiduciary, larceny over $1,200 pursuant to a single scheme, witness intimidation, and publishing a false financial statement.
A restitution hearing has not been immediately scheduled.
Webster told his victims in court on Wednesday, “You all have my assurance that when I get out, I am going to build another company, I don’t know what yet, but I am going to work day and night to make sure everyone gets paid back in full.”