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It happened around 10:30 p.m. on the 3400 block of Rorer Street in the city's Kensington section.
Chopper 6 was overhead as officers cordoned off a garage on the block.
On the ground, neighbors say they knew the situation was bad when they heard the gunfire.
"I hit the ground when I heard the gunshots to take cover," said Romi Rosario, who lives down the street from the shooting. "I'm still trying to process it."
Police say the victims are all men between the ages of 27 and 39.
A 39-year-old man was pronounced dead at the scene after being shot multiple times, according to police.
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Philly police provide update on deadly Kensington shooting
Three other gunshot victims are listed in critical condition at an area hospital. The fifth shooting victim was listed as stable after being shot in the hand.
According to Philadelphia Police Chief Inspector Scott Small, about 50 shots were fired inside the garage.
"We're getting information that three males showed up wearing masks and entered this garage. And we know over 50 shots were fired from a semi-automatic weapon or weapons because we found over 50 spent shell casings," said Small.
This incident marks the 84th mass shooting in Philadelphia since 2020.
The Gun Violence Archive defines a mass shooting as a shooting with four or more victims. There's no clear trend as to where they're happening, but Philadelphia has seen them throughout the city.
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According to the organization, there have been hundreds of people shot in mass shootings in the city since 2020 and 43 have been killed.
"It's like playing whack-a-mole. With mass shootings, you just don't know where this shooter is going to come from," said Mark Bryant, founder of the Gun Violence Archive.
It's all part of a national trend, and it's getting worse.
"The record previously was 2021, and we had 690 mass shootings nationally. I think this year, we're gonna bring over 700, I think fairly easily," said Bryant.
Philadelphia police are investigating the shooting and said they will review nearby surveillance cameras to help determine descriptions of the shooters.
Anyone with information is asked to call the police at 215-686-TIPS.
RELATED: Check the 6abc Neighborhood Safety Tracker