Michael Anthony Vincent Brooke used various ruses, including posing as a council worker and police officer, to trick his way into the homes of his victims.
They included a 98-year-old woman who was fooled into letting him into her home.
Once inside the houses, 49-year-old Brooke would find a way to be left alone so he could steal large amounts of cash and make his escape.
Investigating officer PC Lucy Garside said: “Brooke is a prolific and serial burglar who tricked his way into the homes of some of the most vulnerable members of our community, one of whom is registered blind.
“He exploited these elderly residents, using deception and lies to steal from them in their own homes where they should feel safe.
“Many of his victims had sentimental items taken as well, many of which have never been recovered, which makes his crimes even more appalling."
It was estimated by police that he had stolen as much as £5,000 during the course of his crimes.
On 25 July, Brooke attempted to gain entry to a property in Brick Street, Sheffield.
The resident, a 90-year-old woman, was aware of a burglary at a neighbouring property and challenged Brooke, who was using fake police ID.
The woman called police, who arrived and arrested Brooke around 100 yards from her home.
Forensic evidence gathered from several of the burglaries tied Brooke to those crimes.
Brooke, of no fixed address, pleaded guilty to 16 counts of burglary, two counts of attempted burglary and one count of going equipped.
He was jailed for nine years when he appeared before Sheffield Crown Court on Friday.
PC Garside said: “These elderly men and women have been left frightened as a result of Brooke’s despicable actions and I am pleased that he is now behind bars.
“I hope this sentence provides some comfort to the victims and their families.
“I’d also like to take this opportunity to thank officers in the Performance Crime Teams across Sheffield, who worked together to bring this offender before the courts and ensure justice for the victims.”