The summary of facts says Condon befriended a woman before sexually assaulting her 13-year-old daughter.
A 16-year-old was indecently assaulted while Condon demonstrated some "self-defence moves", the court heard.
Around 1999 or 2000, he approached a teenage school drop-out on a Linwood street and offered her work babysitting his teenage son.
But Condon plied her with alcohol and drugs and touched her while she was in the bath, the summary says. She woke one night after becoming drunk to find that her pants and underpants had been removed and that Condon had unlawfully had sex with her.
In 2006, he approached two CYF runaways on Colombo St and offered them alcohol and babysitting work.
He touched them indecently and asked them to perform sexual acts, sometimes offering money.
Another CYF runaway, aged 13, was given alcohol and indecently assaulted at New Brighton beach.
Defence counsel Anselm Williams said the offending, between 1999 and 2008, occurred around the same time as a "family breakdown". Condon's wife left him, leaving him responsible for the care of his son, while some of his siblings passed away and he was suffering depression.
He's found time in custody "incredibly difficult", Williams said.
Condon also takes exception to the repeated use of the term "child" in a pre-sentence report, claiming that the correct term would've been "young person" for all but one charge.
Judge Tom Gilbert said Condon's pre-meditated and "frankly disgusting" crimes have had a significant impact on his victims, many of whom were vulnerable. The impact is ongoing and likely to continue for years to come, the judge said.
Condon was jailed for four years and nine months. He is automatically placed on the child sex offender register.
