The 22-year-old former Ubuntu FC frontman spent last season on loan with Milford FC and was a part of their promotion winning team, with seven goals.
He has now penned a deal with the Citizens, who will be competing in the Motsepe Foundation Championship for a second time after their unsuccessful play-off bid.
City announced the news on their social media channels: "From the Mother City, for the Mother City.
"We are delighted to announce the signing of Cape Town-born striker, Cheswyn Philander.
"Welcome to the City, Legga!"
