Stephen Webster allegedly diverted millions from escrow accounts to pay for gambling expenses, a boat, a Hawaii vacation, and more.
The owner of a now-defunct South Shore real estate firm allegedly diverted more than $11.6 million from clients and employees in order to fund an “extravagant lifestyle” that included pricey car purchases, a Hawaii vacation, the rent on a Florida apartment, and more.
Stephen Webster was indicted on four charges in in Plymouth Superior Court in September. He faces charges of fiduciary embezzlement, larceny by scheme over $1,200, witness intimation, and filing a false financial statement, according to court documents.
Webster was arrested as a fugitive from justice on Sept. 29 and is being held at the Palm Beach County Jail in Florida.
The details of Webster’s alleged crimes were outlined in court documents filed by Assistant Plymouth District Attorney Alex Zane Wednesday.
Webster, who owned Success! Real Estate, engaged in a “consistent pattern of misuse” that involved the routine use of escrow funds, the charges allege. These client deposits were meant to be held in trust, but instead were used by Webster for a number of business and personal expenses, prosecutors said.
Success! abruptly closed in December 2024. The following month, a dozen brokers who worked with Webster sued him, alleging that he withheld nearly $500,000 in commissions and loan repayments from them. Those losses are not part of the criminal case.
The comingling of escrow accounts and others used by Webster dates back to at least 2023. State investigators began looking into Success! in March of that year. Webster allegedly showed them a forged bank letter showing an escrow account that held about $1 million. In reality, that account only had about $7,000, according to the court documents filed by Zane.
In January 2024, escrow funds became the primary source of liquidity for Webster’s business and checking accounts. Every month, he routinely diverted money from escrow accounts to others in order to pay employees, utility bills, rent on a residence in Deerfield Beach, Florida, casino transactions, mortgage payments, Zelle transfers to family members, and more, the charges allege. Some months, more than 80% of the money deposited into one business checking account came from escrow accounts. He often moved more than $1 million each month, prosecutors allege.
Although Webster diverted more than $11.6 million from escrow accounts, he continued to take on additional borrowing. The timing of these advances and loans coincided with surges in escrow withdrawals, showing that entrusted client funds were the primary source of liquidity for both the business and his personal lifestyle, Zane wrote.
Webster used strategies like “check-kiting” and “high-velocity transfers,” which are both “hallmarks of cash-flow manipulation inconsistent with lawful escrow management,” Zane wrote. The goal was to conceal shortfalls and project liquidity.
Webster made some big purchases. In August 2024 he bought a 2025 BMW 430i for more than $70,000, making an $11,000 down payment despite already paying monthly for two Tesla Model 3 vehicles valued at more than $121,000. He continued paying $8,250 a month in rent for the Florida apartment. He took a vacation to Hawaii, and racked up more than $65,000 in restaurant bills throughout 2024, prosecutors said.
While living in Florida, Webster would regularly fly back up to Massachusetts to “manage” his business, often staying at and gambling in Encore casino in Everett. Last year, he withdrew almost $89,000 from casino ATMs, according to the court filings.
His actions gradually moved from “fiduciary embezzlement into outright theft,” Zane wrote. The alleged scheme became unsustainable in by November 2024, when Webster told creditors that he was “essentially out of money.” He turned to employees for emergency cash infusions. When Success! closed the following month, about $350,000 in outstanding employee loans remained unpaid.
“Even after the company’s collapse in December 2024, the defendant continued making payments on luxury vehicles, jet skis, a boat, and personal credit cards rather than directing resources toward curing escrow shortfalls,” Zane wrote.
Webster made a “last-ditch” attempt to sell the company name in December 2024. During a meeting with potential buyers, he appeared “visibly unsettled” and admitted to a shortfall of about $970,000. One person at the meeting compared the atmosphere to “the Titanic,” Zane wrote.
Webster is also facing a raft of civil litigation, which includes his ex-wife’s attempts to enforce the terms of their divorce. Webster is obligated to pay $3,000 a month in alimony and $10,000 a month for the maintenance of her South Shore home, according to court records.