Stephen Webster arrest

Plymouth County Prosecutors Outline Egregious Case of Embezzlement and Fraud by Stephen Webster, former CEO of now defunct Success! Real Estate

Finally, the law caught up with Stephen Webster of Success! Real Estate, who I am suing for fraud on behalf of a former Success! top agent.

High roller casino suites and thousands of dollars gambling at Encore Boston Harbor Casino, Florida rentals, jet ski’s, and a new BMW and Tesla. These are just some of the purchases that a longtime South Shore real estate broker-owner Stephen Webster of Success! Real Estate made with buyers’ and employees’ funds, according to Plymouth County prosecutors. Today, a grand jury indictment was unsealed, revealing a sordid and shocking tale that Mr. Webster allegedly embezzled over $11.6 Million in escrow deposits, broker commissions, and personal loans from agents, in order to fund a lavish and extravagant lifestyle. The charges detail “business” trips to Florida, Hawaii, Encore, Harrah’s and Seminole casinos where he withdrew over $88,000 cash from ATM’s, a $8,250/month South Florida intercoastal rental property, jet ski’s, and the purchase of a $70k BMWi along with two Tesla’s. Except the source of these funds were innocent victims – buyers, lenders, his agents and others. Mr. Webster went so far as to create a counterfeit letter from his bank in order to throw off the trail of state regulators, prosecutors alleges.

Mr. Webster was just arrested in Palm Beach, Florida, and is reportedly being extradited to Massachusetts to face these charges. Prosecutors are seeking $100,000 in bail due to Webster being a flight risk. The charges include fiduciary embezzlement, larceny, witness intimidation and publishing a false financial statement.

I wrote about this case back in January 2025 when Webster suddenly closed shop, leaving buyers and agents scrambling to recover their deposits and commissions.

Since Mr. Webster abruptly closed his company last year, he and his company have been sued by a slew of agents and buyers who are scrambling to recover millions in unpaid commissions, deposits on pending transactions, and even personal loans given by agents to Webster in an attempt to keep the firm afloat. One of these lawsuit is one that I filed in Norfolk Superior Court on behalf of a top agent.

More detail on the charges can be found below. I’ll have updates once Mr. Webster appears in court.

Commonwealth of Mass. v. Stephen Webster, Plymouth Superior Court by Richard Vetstein

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