Stephen Greenwood, 55, pleaded guilty at Warwick Crown Court to four counts of fraud, worth more than £19,000, and asked that a further 59 counts of fraud worth £50,000 be taken into consideration.

He was jailed for stealing rental payments from clients for properties he managed.

Greenwood had run a letting agency in Rugby since 1985, but ran into severe money problems when a Spanish property investment failed to pay out on time.

The court was told by prosecutor Michael Hanning that Greenwood attempted to prop up his business by “robbing Peter to pay Paul”, collecting the rents for properties he managed but not passing the payments back to the homeowners.

Fake statements claiming the money had been paid continued to be sent to his clients.

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The fraud was discovered when Greenwood’s business went into liquidation at the end of 2009, owing £329,000.

Michael Brook, in mitigation, said Greenwood was “a man of good character who suffered a catastrophic fall from grace”.

Greenwood had believed he would be able to repay his clients once the money he was owed from the Spanish investment came through.

Judge Charles Harris QC said: “This is a sad case, because you come from a good background and are an intelligent man. It is difficult to see how cases of this kind can be dealt with other than by a custodial sentence.”

Greenwood has also been banned from working as a company director for four years.