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43-year-old James Delaney had targeted the couple in their 70s, telling them that repair work was required on their roof.
Initially he told the couple that there were several loose tiles, the chimney needed to be corrected and the flue needed to be removed, which would cost £400.
He also checked the guttering and advised that it needed to be replaced, pricing the whole system at £1500.
The victim paid £200 upfront, to pay the rest the following day when Delaney came to carry out the work.
After some concerns were raised by neighbours, the police were called and turned up the following day at the same time as Delaney.
It was later confirmed by an expert that the actual value of the work carried out was around £75, the flue did not need to be removed and the guttering did not need to be replaced.
The 43-year-old, who had previous convictions for similar offences against elderly people in Leicester and Northampton, pleaded guilty to fraud, and dishonestly making a false representation that this work was required, contrary to sections 1 and 2 of the Fraud Act 2006.
DC Marina Lee, of Hartlepool CID said: “Preying on the elderly and conning them out of large sums of money for work that does not need to be carried out is particularly cruel.
“I am pleased that Delaney has been given a custodial sentence which will prevent him from carrying out this fraudulent activity for a while.
“I would urge people to keep an eye out for elderly relatives and neighbours, and ask them to let you know if anyone approaches them directly for work to be carried out.”