On December 14, 2024, Success Real Estate — a 140-agent brokerage with offices in Marshfield and Braintree, Massachusetts — locks its doors without a single word of warning to anyone. No notice to the agents. No notice to buyers with money sitting in escrow. No explanation. The phones stop working. The offices go dark. Agents who closed deals weeks earlier start calling each other trying to figure out where their commission checks are. Buyers with pending transactions suddenly have no closing agent. And the man who owns the whole operation, broker-principal Stephen Webster, is in Florida.
He has been spending a lot of time in Florida. Court filings lay out an $8,250-per-month apartment on the Intracoastal, high-roller casino suites at Encore Boston Harbor, Harrah's, and the Seminole casinos, where Webster withdraws more than $88,000 in cash from ATMs during his stays. There are two Teslas and a $70,000 BMW. Jet skis and boats. A trip to Hawaii. And $65,000 spent at restaurants in 2024 alone. On certain months, prosecutors say, Webster's spending exceeds one million dollars. Every dollar of it belongs to someone else.
What Webster has been doing for years is treating the escrow accounts of his real estate firm like a personal operating fund. Client deposits, closing funds, and money earmarked for pending transactions flow routinely out of designated escrow accounts and into Webster's personal and business accounts. His own agents, trusting the man they work for, extend him personal loans to help keep the brokerage running. He never pays them back. The Massachusetts Department of Licensure opens an audit in 2023 and asks for documentation of escrow holdings. Webster submits falsified records and omits an entire account from the disclosure. When a regulator examines a bank letter he produces showing more than one million dollars in escrow, the actual account holds $7,000.
The brokerage closes in December 2024. More than fifteen lawsuits are filed almost immediately. Agents cannot recover their commissions. Buyers cannot close their transactions. Some of the people Webster borrowed money from personally will never see it again. He is named a fugitive from justice and arrested in Palm Beach County, Florida, in September 2025, extradited to Massachusetts, and indicted in Plymouth County. On April 1, 2026, Stephen Webster stands in Brockton Superior Court, pleads guilty to embezzlement, larceny, misleading investigators, and publishing a false financial statement, and is sentenced by Judge Daniel O'Shea to two to three years in state prison followed by five years of probation — during which he is barred from ever again holding a position of fiduciary responsibility.