Cherry, who had covered his face with red bandannas, pointed a homemade taser at the woman and told her not to make him use it on her.
The victim went to her wallet and grabbed all the money out of it - $10 in coins - and gave it to Cherry, who pocketed the cash.
He then looked at her nearby tablet, but quickly retreated when the victim started yelling loudly that it was her tablet and he wasn't to take it.
It was then that Cherry fled the house.
"When you were ultimately spoken to by police you admitted what you had done and said you simply wanted to scare and frighten the victim by taking the homemade taser with you," Judge Hobbs said.
A psychiatric report spoke of Cherry's immaturity and limited insight into his offending and the way it affected others.
"It seems that you thought this would simply be funny and that you only meant to scare the victim."
The report suggested Cherry might have been "egged on" and could have been committing the crime to show off to others.
It has disrupted her life in a fundamental and significant way.
Judge Hobbs said the offending had a big impact on the victim and her family.
"It has disrupted her life in a fundamental and significant way. She has had to move out of her house that she felt safe and comfortable in . . . she no longer feels safe living in the community is which she felt safe and settled."
Cherry was on release conditions at the time of his offending.
Judge Hobbs said Cherry had a "particularly troubled background", including "a traumatic childhood characterised by abuse, neglect, domestic violence, parental alcohol abuse, and multiple changes of homes".
"You have a very poor sense of what is appropriate behaviour."
Cherry is assessed as being at a high risk of reoffending.
He pleaded guilty to a charge of aggravated burglary as well as unrelated charges of trying to unlawfully take a motor vehicle and possessing tools to do so.
Judge Hobbs sentenced him to five years and four months in prison.
