In spring 2012, Winter signed on to another DC Comics produced series, Arrow. After starting as series Cinematographer, he segued to episode directing. His first effort was written by frequent collaborator, and DC Comics CCO, Geoff Johns. Entitled "Dead to Rights", the installment was met with fan and critical acclaim. He went on to direct second season episodes "Broken Dolls", "Blind Spot", and "The Promise".
He served as the Director of photography on the pilot of Arrow's sister-series The Flash. He went on to direct the fourth episode, "Going Rogue", in which the supervillain Captain Cold is introduced. He next helmed the series' 8th installment, which features a crossover event with Arrow, "Flash vs. Arrow"; and the 13th "The Nuclear Man", featuring the exploration of the titular hero. During the latter portion of the season, he was named as Producer.
In September 2015, it was confirmed that Winter would helm the pilot for the Arrow/Flash spin-off Legends of Tomorrow. The series focuses on a band of tag-team heroes and villains made up from the Arrowverse, traveling through space and time to stop the maniacal Vandal Savage. It was later confirmed that Winter would also serve as a Producer on the series. Winter said of directing the two-part pilot episode that he was most proud of a technically challenging battle involving The Atom. "He flies out of [Martin] Stein's pocket. [The creators] write, "Atom basically comes in and shoots up the place." I'm like, "Oh, my god. How am I going to do that? What is that? What does that even look like?" I decided I didn't want to do it in a bunch of cuts. I wanted it to feel like one flowing, big piece. I shot it on the camera car. I shot it on high-res at 6k. We did it in one take."
