It was only half of what had been stolen during a seven-month spree of break-ins, which he committed alongside 32-year-old Benjamin Burgess.
Winter said the crimes were driven by his severe addiction to methamphetamine.
That was underscored by a report before the Parole Board which listed his risk factors as poor self-control, impulsivity, criminal associates, lifestyle balance, and substance abuse.
Winter said he had started using meth at the age of 39. All but one of the burglaries occurred when families were out or on holiday and most targeted more affluent suburbs, such as Māori Hill, Belleknowes and Waverley.
The offences, panel convener Judge Geoffrey Ellis said, "caused great distress, insecurity, and feelings of violation to the victims".
Winter's criminal history began in 1993 and included convictions for rape, unlawful sexual connection, arson and 21 burglaries.
"He had previously been undeterred by repeated imprisonment or rehabilitation programmes offered over the years," Judge Ellis said.
Winter had completed more treatment while at the Otago Corrections Facility and had been working at the prison's dairy farm.
Before he was transferred to Invercargill Prison in February, though, his file was marked with a misconduct after he was implicated in smuggling contraband.
Winter denied any involvement.
Corrections described his behaviour as "polite and compliant" since he moved further south.
Among Winter's parole conditions were: To live at an address approved by Probation; not to contact victims; not to contact Burgess; not to possess alcohol or illicit drugs; to attend any treatment as directed; and to obtain approval before changing employment status.
