Ryan Mulvaney, 45, climbed through an open window at the house in Stonefall Avenue, Harrogate, where he stole an envelope containing £1,000 from the living room.
Mulvaney, who was with another man, then climbed back out of the window with the stolen cash just as the victim - who had only been living at the property for four months - came into the living room after hearing noises from his bedroom, York Crown Court heard.
Prosecutor Matthew Collins said the victim had earlier been advised by his mother over the telephone to open a window to let in fresh air to help him feel better.
He saw the backs of the two intruders as they climbed out of the window and disappeared into the night with his cash.
Mulvaney, who has over 100 offences on his record including robbery and serious violence, was ultimately arrested and charged with burglary. He admitted the offence and appeared for sentence via video link on Wednesday after being remanded in custody.
The burly, musclebound defendant, of Knaresborough Road, Harrogate, was on prison licence at the time of the raid in the early hours of August 25 last year - which was just 10 days after he had been released from his last prison sentence.
“The (named victim) was in bed, feeling ill, when he heard a noise in the living room,” said Mr Collins.
“Going through (to the lounge), he saw that a rear window – left open for some air as he was feeling unwell – was being used by two males who were climbing through the window and out of the address.
“A quick check of his property revealed that an envelope containing around £1,000 had been stolen from a storage box under his window. That money had been used to renovate the house.”
The burglars’ fingerprints were later found on the window, added Mr Collins.
The “opportunistic” raid was Mulvaney’s eighth house burglary in a criminal career spanning nearly three decades and which also included numerous burglaries at commercial premises.
He had 31 previous convictions to his name for nearly 120 offences including wounding in the course of a burglary, fraud and handling stolen goods. He had served numerous long prison sentences over the past 20 years.
Kelleigh Lodge, for Mulvaney, said the father-of-one’s offending was to fund a serious drug habit.
She said that when Mulvaney was released from his last prison stretch in August 2019, he relapsed and broke into the house in Stonefall Avenue within days of regaining his freedom.
Jailing Mulvaney for three years and four months, judge Simon Hickey told him: “This was an unpleasant and opportunistic offence, presumably carried out by you because you were desperate for drugs. You are, in my judgement, a member of a group or gang.”
A second man who was arrested and charged with burglary in relation to the same incident is due to appear in court in the near future.