‘Notorious thief’ facing new charges

Jeffrey S. Windle attempted to purchase two multimillion-dollar homes with fraudulent checks.

Jeffrey S. Windle will appear before a judge for a pretrial hearing in February. —MV Times

Nearly three years after attempting to purchase a $15 million house in Edgartown with a fraudulent $2 million check, convicted embezzler and Oak Bluffs resident Jeffrey S. Windle again faces charges of larceny by check and larceny by false pretenses.

Due to prior convictions spanning almost three decades, police are charging Windle with being a “common and notorious thief.” He was arraigned at Edgartown District Court in November. 

In May 2022, Edgartown Police officers followed up on allegations made by a local real estate broker that a month earlier, a man using the name Jeffrey C. Stewart had attempted to put a $20,000 down payment on property in Tisbury. The broker alleged that the man was using a photograph of a check connected to a bank account opened in January that had insufficient funds to cover the charges.

The real estate agent told police that at the end of April, he had entered into a purchase and sales agreement with Stewart — later identified as Jeffrey S. Windle — for two properties in Vineyard Haven. At the time, Windle was accompanied by a female companion who police determined had also been conned into believing Windle was Jeffrey Stewart, and that he was a man of significant means.

The woman, who had met Windle on a dating website weeks earlier, told officers that he presented himself as “a nice guy” who was in the process of purchasing houses as part of his trust, She told police that he even took her to Cape Cod to look at properties off-Island. 

“She [had] no idea what Mr. Windle was up to, and was caught completely off-guard when she received an email with his real name,” police reports say. “She was under the impression that he was Mr. Jeffrey Stewart.”

After entering into a purchase agreement for the neighboring Tisbury properties, the real estate agency never received the down payment check, which was promised to have been sent in the mail, the police report states. Costs associated with home inspections of the two properties were also left unpaid, after it was found that the checks sent to the home inspectors were connected to a bank account with insufficient funds. 

By the time the real estate brokers contacted authorities, it was determined that Windle was already in the custody of the U.S. Marshals Service for past crimes.

Windle has been charged with numerous counts of fraud-related activity going back as far as 1996, when he was found guilty in Worcester of forgery, larceny, larceny by credit card, and uttering a forged instrument.

Then in 2009, according to court documents, Windle admitted to writing and depositing a number of unauthorized checks and embezzling millions over the span of years — including roughly half a million dollars from his own church; he pleaded guilty to a 24-count indictment in a Boston federal court, which included money laundering, wire fraud, mail fraud, and tax evasion, and was sentenced to 15 years of imprisonment, followed by three years of supervised release, and ordered to pay more than $14 million in restitution. 

Upon his release in 2020, Windle was found in violation of the terms of his release, by — among other things — attempting to purchase a $4 million home in Barnstable under the name Jeffrey Whitney. Then in 2021, using the alias Jeffrey Leonard, Windle placed a deposit on a $15 million Edgartown property with a $2 million check that was drawn on an account with insufficient funds

Now, having been released once again from federal custody, Windle is slated to appear at Edgartown District Court for a pretrial hearing in February for his most recent charges. 


  1. Gee this criminal has had a lot of practice making his business model am art form. Why did the Fed’s let him go ??

  2. Soooooo………was he just posing as a millionaire to impress a girl??? I mean, obviously when the check bounces he dosent get the mansion!!

  3. That swindler shows more diligence and dedication to his craft than many of our politicians.
    I say sentence him to lectures about work ethics to Congress (about to recess for the long holidays).

  4. He should team up with George Santos and start a new real estate office named: P.T. Barnum’s Fabulous Discount Properties.

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