Emergency crews were dispatched to the scene on Grandravine Drive, near Jane Street and Finch Avenue, shortly after 1:30 p.m. ET.
O'She Doyles-Whyte, 16, was found without vital signs when police arrived and his friend 15-year-old Kwame Duodu was rushed to a trauma centre in life-threatening condition.
Duodu would later succumb to his injuries in hospital.
In the wake of the latest shooting in the Jane and Finch area, friends of the boys known in close circles as Oshe and Kwame expressed their grief online.
"Looking at My Phone For A Good Morning Msg , But I Member Your No Longer Here With Me....," tweeted @__ItsMickey about Doyles-Whyte.
"3 weeks ago I was just working with them & now there gone no warning signs or nothing. Life to short man...RIP Oshe & Kwame," @yv0nne_ wrote.
If he saw us crying like this, he'd make sure we were okay. His smile would take away all my pain, Kwame please come back," @Forever_Afiaa.
A resident of the neighbourhood who knew the boys and described them as "good kids" and "respectful."
"I'm very emotional. I can't believe it," said Alisha. "You never think it will really happen until it does happen."
The shooting is the latest in a string of fatal incidents involving teens in north Toronto that police are investigating for possible links.
On Saturday, a funeral was held for 15-year-old shooting victim Lahj Loor Walters.
The teen was shot several times in the Yorkwoods Gate Plaza parking lot near Jane and Finch after two men in a vehicle approached him at around 10 p.m. on July 28.
Walters was taken Sunnybrook Hospital with life-threatening injuries and police issued a statement last week saying that he had died in hospital.
"Imagine Oshe and Kwame would have went to Tahj's funeral today.. This world is on one," tweeted @_Klxo earlier Saturday.
With police tape still clinging to the fences and trees on Grandravine Drive, police canvassed the neighbourhood for witnesses that could help them in their investigation.
Det.-Sgt. Terry Browne with homicide squad said police are looking for three "young" people last seen leaving the area on bicycles shortly after the shooting.
A statement released by police describes one of the suspects as black and the other two as "possibly Somalian."
"Our investigations are only as good as the people that come forward," Browne said. "This is a tragic event, two young people have lost their lives, and we certainly want to do all we can to bring the person or persons responsible for this to justice."
Toronto Community Housing Board chair Bud Purves and president and CEO Gene Jones issued a joint written statement on Friday that said they were "angered and saddened" by the violence.
"Our first thoughts are with the families and friends of the two young men shot today, and with the entire community of Yorkwoods Village," the statement said.