Andrew Harley, 28 of Mill Bank, Wellington, stole from sheds, garages and outbuildings around the town.
He was sentenced for taking thousands of pounds worth of bicycles, vinyl records, tools and more.
Shrewsbury Crown Court heard that Harley, who had 39 previous convictions for theft and dishonesty, had “only ever known” a life of crime.
He would sell some of the items he stole at Cash Converters and keep others, which police found when they raided his home.
Kevin Jones, prosecuting, told the court that some time between February 16 and March 22, Harley stole pottery, records, a bike, a helmet and a drill from a shed on Mill Bank in Wellington.
He said that the value of these items came to between £3,000 and £4,000.
On another occasion Harley stole four bicycles, in total worth £2,000.
Mr Jones said: “Twenty one items were taken on one occasion, which suggests that he has returned to the property more than once; he would not have been physically able to carry it all.”
Harley also stole from sheds on New Church Road and Ercall Lane.
Harley pleaded guilty to some of the burglaries in June, before admitting two more this week and bringing the total to nine counts of burglary.
Representing Harley, Rebecca Wade conceded that he had an “appalling” track record for theft.
But she said that he suffered from a drug addiction and attention deficit hyperactivity disorder, and was trapped in a “vicious cycle”.
She said: “That cycle is the reason for his offending. He would steal items that can easily be stolen, to exchange them for money.
“This defendant has told me that all he has ever known is crime. His first period of incarceration was when he was 14.”
Judge Peter Barrie told Harley: “Between February 16 and April 26, you committed a series of nine offences of burglary from sheds and garages in the Wellington area.
“Some of these thefts were of high value items, which caused substantial and troubling loss to the people who have lost them.”
He handed down nine jail sentences of two years and six months to run concurrently, one for each count of burglary admitted.
Harley will also pay a victim surcharge when he is released.