The women, aged 31 and 32, were allegedly targeted while alone in their own homes in Sydney's southwest in two separate break-in attacks over a matter of days.
Police said they responded to two reports of home invasions, one in Arncliffe about midnight on Tuesday and a second about 12.30am on Thursday in Bankstown.
Detective Superintendent Virginia Gorman said the men forced their way into the Arncliffe property before threatening a 31-year-old woman with a knife, sexually assaulting her and taking off with her money.
The woman was treated in hospital for minor injuries.
Just two nights later, the same men forced entry into a Bankstown home and allegedly assaulted a 32-year-old woman.
The woman was also taken to hospital for treatment of minor injuries.
"These men had done some research and they believed that these women might be home alone and they might have money on the premises ... so they were specifically targeted," Det Supt Gorman told reporters in Sydney on Friday.
Police believe the men were on their way to target another person, potentially on Thursday night.
Det Supt Gorman described the alleged attacks as "very violent".
"Excessively violent for three men armed with a weapon against vulnerable women home alone," she said.
"They were armed with a knife. They used duct tape to restrain them. They had duct tape over their mouth.
"They assaulted the women, punching a woman. You don't need to do that to overcome a solo female.
"The violence was over the top for what they've done."
Detectives executed three search warrants across greater Sydney about 7.45pm on Thursday with assistance from the riot squad.
Officers arrested a 20-year-old man in Belmore and charged him with a slew of offences, including two counts of choking someone, depriving someone of liberty, assault and aggravated robbery.
In Punchbowl, 19-year-old, Arman Nangyal, was arrested and was charged with offences including two counts of choking a person, aggravated sex assault, aggravated break and enter, robbery, use of an offensive weapon and other offences.
He appeared briefly in a grey singlet in Bankstown Local Court on Friday via video link where no application for bail was made.
His matter was sent to Burwood court for next mention on November 18.
An 18-year-old, Adam Fakhouri, was arrested in Greenacre and charged with two counts of choking a person, aggravated break and enter and deprivation of liberty among other offences.
He did not appear in Bankstown Local Court and made no application for bail.
His matter will travel with the co-accused to Burwood Local Court.
The 20-year-old accused was also due to face Burwood Local Court on Friday afternoon.
"Physical injuries can be overcome easily," Det Supt Gorman said.
"It's the mental injuries of having a person invade your home and do that kind of violence, that would be a long time for them to recover from."
1800 RESPECT (1800 737 732)
National Sexual Abuse and Redress Support Service 1800 211 028