Winslow, 34, was charged with kidnapping with intent to commit rape, forcible rape, forcible sodomy, forcible oral copulation, residential burglary and indecent exposure, according to the San Diego County Sheriff's Office.
Winslow's five reported victims range in age from 54 to 86 years old.
Winslow pleaded not guilty to all charges.
The former player was also arrested in a different incident in Encinitas, Cali. on suspicion of burglarizing a residence at the Park Encinitas Mobile Home Park.
Winslow reportedly fled the scene in a black SUV and deputies spotted him a short distance from the park and he was taken into custody.
Winslow's bail has been increased to $2 million. He was ordered to wear a GPS monitoring and also to surrender his passport.
Winslow was drafted to the Cleveland Browns in 2004.