Winslow will be placed on house arrest under terms of bail and is scheduled to have a hearing in August.
The 34-year-old was arrested multiple times in June and initially faced nine criminal charges, including kidnapping, rape and indecent exposure. He was also accused of breaking into homes in a mobile home park with the intent to rape elderly women.
The attacks for which Winslow is accused took place between March through June.
On Thursday, USA Today's Josh Peter reported that Winslow has also been charged with raping an unconscious 17-year-old in 2003. Winslow was 19 years old at the time.
Last month, a judge denied Winslow bail because it was deemed he "presented a threat to society." According to TMZ, bail was set at $2 million on Thursday for the former Cleveland Brown—who made more than $27 million in his NFL career, per Spotrac.
Winslow faces life in prison if convicted.