Alan Eastham has 26 convictions for 72 offences, with many of his victims elderly or vulnerable.
He knocked on an 86-year-old widow’s door at 3.15pm on October 8 and offered to sweep the leaves up in her porch.
“She went out with a coffee and had taken a piece of cake for him as well.”
But after tricking his way in by asking where he should put the shovel, Eastham left with her handbag - which contained a picture of her late husband, and £200 - and the cup and plate.
Police found the cup dumped nearby and a forensic inquiry revealed Eastham’s DNA.
In a statement the pensioner, who suffers heart conditions, said: " The burglary has made me feel shaky.
" I'm more nervous now. I've been eating less and not wanting to go out.
"I've been very upset over the weekend and do not want to answer the door.
"In addition I've had a few health conditions which I've had to overcome and I feel like this incident has caused me a significant set back. "
She added she was struggling to sleep and was nervous in her own flat and had to have tablets to settle her tummy.
She added: "It is an invasion of my privacy and my own home which is not right under any circumstances."
Eastham appeared to wipe away tears in the dock as Sharon Watson, defending, explains the offences were committed out of desperation, as the dad-of-three's 10 year relationship came to an end and he was asked to leave the family home.
Due to his previous offences he was not welcome with his family in Preston and ended up homeless.
There were issues with his claim for Universal Credit and he effectively ended up penniless.
At one point he had lived in the disabled toilets between Asda and Sainsburys.
He did obtain accommodation but got into debt with utility companies due to the delay in receiving benefits.
She added: "He has expressed his remorse and shame."
Sentencing, Judge Robert Altham said: "She made you welcome. She offered you coffee and you tricked her into allowing you into her home so you could steal her property, because once you cheated your way into her living room you took her handbag.
"It contained other items, including a photo of her husband, which I will assume was later recovered once the bag was recovered - after you had rifled through it.
"The cup, which had been the vehicle of her kindness to you, contained your DNA and you were arrested.
"I have no doubt this will fall on deaf ears because I've seen your offending history. But when you burgle someone's home you don't only invade their property, you invade their sense of security, their sense of who they are.
"You know you take that risk... you don't seem to care."
The judge told Eastham he had an "extraordinary record" and that previous jail terms for similar offences had been absolutely no deterrent.
He added: " None of his history can explain why his response to his misfortune is to target the old and vulnerable, to affect their lives."
He imposed a 50 month jail term, and for the OAP's "peace of mind", imposed a 10 year restraining order.
The sentence will be served consecutively to an existing 18 week jail term.