Cash, mobile phones and a child’s clock that was supposed to be a Christmas present were among the items stolen by Jason Finney between December 13 and 17 last year.
Police officers tracked him down the day after one of the burglaries when he was seen fast asleep in a stolen Renault with the missing items from the property.
Prosecuting barrister Simon Parry said the car, which had been hired by the Ministry of Defence, had been taken from one of the addresses.
Initially Finney, 43, of Willowfield, Woodside, claimed that someone asked him to look after the stolen goods, which include electronic devices.
He snuck into a home near Royal Shrewsbury Hospital where he was captured on CCTV on December 13, but was confronted by the “traumatised” householder and fled on foot after saying “sorry”.
He was linked to three of the scenes by the pattern on his trainers.
On December 16 he snatched a mobile phone, two bottles of wine and a bottle of vodka from a house in the Oakley Manor area, along with gifts under the Christmas tree including a Disney clock and a vase.
The following day £250 cash and a Post Office card were stolen from a handbag left in a kitchen at a dwelling in South Hermitage. On December 24 premises in Glendale Court were broken into and items along with the Renault were taken.
Mitigating barrister Miss Debra White said: “He understands that he is going to be sent back to custody. With clarity, he understands the trauma and upset that his behaviour caused the householders.”
The court heard that Finney had 55 convictions relating to 124 offences dating to 1989 and that 65 offences were thefts.
Jailing him for two-and-a-half years at Shrewsbury Crown Court, Judge Peter Barrie said: "This is a desperate story isn't it. I think in the last few years you must have spent more time in prison than out of it.
"One of these days you will face up to your responsibilities to your partner and your children and find the strength to of character to overcome your issues with drugs.
"I see that in October last year the court gave you a community order in the hope of helping you to do that, but as Christmas approached you carried out these burglaries, clearly destined to get money and paltry amounts when compared to the upset and distress caused by offences such as these."
"It is time that you grew up and do some serious thinking. It's no good coming out of prison again and again and coming back to this sort of behaviour. This time in prison will give you thinking time."
Finney pleaded guilty to burglary and handling stolen goods.