Aaron Croft also snatched an estimated £50 from a snack trailer in Telford where the operator had given him free food because he was homeless.
The 35-year-old was arrested after he struck at four different properties in January this year.
Mr Mohammad Hafeez prosecuting barrister said on January 5 he stole a television and computer devices from an address, in Doddington Road, Hollinswood, leaving his shoe print on the carpet and a cigarette lighter which were later matched to him.
On January 21 he entered the snack food bar near Telford Shopping Centre after the owner, whom he knew, briefly left it unattended and stole cash from the till.
The following day Croft stole goods including a watch from a home, in Withywood Drive, Malinslee, while the family slept again leaving behind his footprint.
Then on January 23 a family at another property in the town woke up to find immigration documents along computer devices and a designer handbag valued at £2,350 missing.
Mr Hafeez said Croft was caught following this house burglary.
"Witnesses called the police after some of the items were found discarded nearby and close circuit television cameras had captured the defendant inn the vicinity.
"He was arrested on January 23. Some of the items were found still in his possession. He appeared at the magistrates court on August 28."
Croft pleaded guilty to burglary and theft.
The court heard he has previous convictions dating to 1999 including for burglary and motoring offences.
At the time of the latest offences he was already subject to a conditional discharge for shop theft.
Mtigating on his behalf Miss Debra White said: "At the time he was living in a tent. He is sorry for the impact his behaviour has had on the homeowners. He has been in custody since his arrest in January," Miss White said.
Croft was jailed for a total of two and half years for all the offences. He must serve half before being released on licence. There was no order for compensation.
The defendant, of no fixed address, told Judge Peter Barrie he would apologise personally to the trailer owner on his release.