Teenager Reece Ballantyne has been locked up for 27 months after being caught burgling again in Hemel Hempstead.
Ballantyne, 18, had gone with another youth to a house in Great Elms Road and asked the woman there if she needed her windows cleaned.
When she said she did not want his services he started playing with the light switch in her hallway, St Albans Crown Court heard.
Prosecutor Laura Blackband said the woman asked him: “Are you drunk or high?”
Ballantyne, pictured, who was wearing a red shirt, said something about crack cocaine. After a confrontation with the woman over her dog he left.
Fifteen to 20 minutes later, Ballantyne was on his own when he was captured on a family’s CCTV system stealing a laptop from a house in nearby Oliver Road. A Blackberry phone was also taken.
Police were called after the family returned. When officers viewed the CCTV tape they recognised Ballantyne and he was arrested at his home that night. He was still wearing the red T-shirt, said the prosecutor.
When questioned he made partial admissions, admitting he had been in the area but denied committing the offences. The laptop bag was recovered after a search.
Ballantyne, of Widmore Drive, Hemel Hempstead, appeared for sentence having pleaded guilty to one charge of burglary and one of attempted burglary.
He was in breach of a Youth Rehabilitation Order passed by West Herts Magistrates in April. He had a long list of previous convictions including three residential burglaries, theft, handling and possessing drugs.
Defence barrister Kyriakos Argyropoulos said Ballantyne had faced problems in his life, some of which were of his own making.
On Thursday, Judge Michael Baker QC sentenced him to 16 months for the burglary and attempted burglary with a further 11 months for breaching the Youth Rehabilitation Order.