Matthew Moore, from Birmingham, carried out a total of six raids – and one attempted burglary – between January 30 and March 30 this year.
The 35-year-old, who said he was driven by his drug addiction, broke into the home of a man in his 70s while wearing a clown mask.
Another man in his 70s, who Moore had previously done gardening work for, was also targeted – with the pensioner left with bruising after a scuffle, with his wallet also taken.
Moore carried out the raids over two months in Shard End and Chelmsley Wood – taking jewellery, cash, electrical items and a car.
Police officers caught the offender after finding his DNA on a top he left behind at one of the break-ins.
Police raided his home in Barlands Croft, Shard End, and found a range of face coverings – and a red screwdriver which was matched to CCTV footage.
Moore, who is unemployed, admitted to the offices during a police interview and was sentenced at Birmingham Crown Court on Thursday.
He pleaded guilty to six charges of burglary, one attempted burglary and one theft of a vehicle and was jailed for six years.
Dc Karen Kirman of Force CID, said: "These were all frightening offences against the elderly and vulnerable in their own homes, mainly in the middle of the night, and Moore often went in with his face covered up.
"He was a prolific offender and all his victims have been deeply affected by what has happened to them.
"But we hope that this sentence will bring them some comfort from knowing that he is now behind bars."