He was already a dangerous young man when, at 25, he fatally beat and strangled the young woman, who had showed him nothing but kindness.
But when he committed murder again nearly three decades later he showed he remained a dangerous person who places no value on the life of another person, Justice Andrew Tinney said.
It was only after Chalmers was sentenced to life behind bars for the murder of 60-year-old Dianne Barrett in Western Australia in 2021 that he was even arrested for Ms Steward's killing in Geelong in 1992.
He was charged in March this year and pleaded guilty to murder in September.
Justice Tinney handed down a second term of life behind bars on Monday.
Chalmers had been ordered to serve at least 20 years before being eligible for parole for Ms Barrett's killing.
He must now serve at least 36 years and is likely to die behind bars, Justice Tinney said.
Chalmers had visited Ms Steward's home with her partner and other friends on the evening of March 16, 1992.
Chalmers returned later that night, telling the kind mother of two children, then aged 10 and 13, that it was his birthday and he had no one to celebrate with.
She invited him in for a while and when he asked to sleep on her couch, Ms Steward agreed and headed off to her bedroom.
An hour later Chalmers took an iron from her living room and beat her with it until she was unconscious.
He then took an extension cord and wrapped it tightly around her neck for several minutes until she was dead.
Chalmers then hooked the cord under her mattress to keep it tight before he left the house.
After several days trying to reach Ms Steward unsuccessfully, her former housemate let himself into her home and found her body.
Chalmers was interviewed by police at the time, but was only captured after he confessed his crime to undercover police in January 2020.
He repeatedly told police he wasn't sure why he'd killed Ms Steward but he "just did it".
While Justice Tinney heard Chalmers was remorseful for killing Ms Steward, the judge wasn't sure that was the case given his violent actions years later.
He murdered Dianne Barrett in May 2019, using his hands and a metal bar to choke her after she went to his home for a cup of tea after a meal at her house.
Seven months later he confessed to that crime, telling police he didn't know why he'd killed her either.
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