Lee Burgess, aged 48, of Deer Park Road, Stannington, has been sentenced to seven years for conning his way into two homes.
He admitted burglary, theft and burglary with intent to steal.
He even persuaded one of his victims to make him a cup of tea while he was in her house - before he stole her savings of £2,000.
Investigating Officer Jo Swift, of South Yorkshire Police, said: “Being the victim of a burglary can be a particularly traumatic experience. Burgess tricked his way into his victims’ homes where they should feel safe.
“He stole £2,000 from his second victim – money she had been saving for a number of years. He even got her to make him a cup of tea whilst he deceived her, pretending to be helping with odd jobs.
“I would like to praise both victims in this case. Burgess has now been sentenced to a significant amount of time in prison where he will be able to reflect on his despicable actions.”
The court heard how the two offences happened on Saturday, October 30, 2021.
Burgess firstly called at the door of an elderly woman, aged in her 70s and who suffers from dementia, in the Stannington area.
Arriving at 7.35am, he claimed he was there from the council to drill some holes.
He went inside her property and into the bedroom before leaving.
Nothing was actually taken in the incident, but when the victim’s family checked CCTV they called police and an investigation was launched into the suspicious activity, treating it as an attempted burglary.
The second offence occurred at 8.25am when Burgess knocked at the door of a property in Hillsborough.
Once again, Burgess claimed to be from the council and said he was there to cut the bushes at the front of the house.
After the victim, aged in her 60s, made him a cup of tea, Burgess explained he could fit some bolts to the back gate for £5.
After going upstairs to get Burgess the money, the victim returned to find him in the living room. Burgess then once again distracted the woman by saying he needed some ladders. He then left via the gate, taking his cup of tea with him.
During the investigation Burgess was recognised from the CCTV footage from the first incident. He was also electronically tagged at the time, so his movements that morning between both properties were able to be tracked.
He was arrested on November 3 and a search of his home found several items of clothing which appeared to match that in the CCTV footage.
Investigating Officer Swift added: “If someone calls at your door and they don’t have an appointment or you are not expecting a visit then please ask for their identification and take a good look at it. Genuine callers won’t have a problem with you verifying who they are – they will not mind you calling to verify their identity.
“If you have a chain on the door then ensure it’s on if you don’t know who’s there. Genuine callers won’t try and pressure you to let them in to your house.”