It happened around 9:20 Sunday night on the 6200 block of Walton Avenue.
Police arrived to find a man in his 30s suffering from multiple gunshot wounds. He had collapsed on the street.
A 61-year-old woman, who police say was an innocent bystander, was shot in the leg.
Both victims were taken to the Hospital of the University of Pennsylvania.
The male victim is in critical condition. No word on the condition of the female victim.
Authorities believe at least two semi-automatic weapons were used. They say 31 shell casings littered the area.
One home on the block was left riddled with bullets throughout the first floor.
"The projectiles, the actual bullets, four of them struck a private residence. Of the four that struck the residence, many went through the front window and ended up in the living room wall," said Chief Inspector Scott Small, Philadelphia Police.
Six people, including four young children were home at the time but were on the second floor and escaped any injuries.
One suspect was seen fleeing northbound on Cobbs Creek Parkway in a white vehicle.
Police believe the shooting may have stemmed from a fight over a woman at a party on Saturday.