did winston die?

It depends what you mean by dead. Physically Winston is not dead. The author makes it seem like he died but if you listen to the reading you notice that he is not really dead, it is just that everything he believed in is gone. He is mentally dead. He stopped loving Julia. Winston finally believed that 2 + 2 = 5. And he finally, after all the fighting and rebelling, loved big brother. Even though his body is still alive and he still can continue his life, I think that he is dead inside. Or at least it is the something like that. I think this because he went through a lot to just end up believing what the party wanted him to believe in. He gave up his love just to follow big brother and save this own life. He changed his own mind set. It is like he became a new person. Like the old Winston died and he became someone new.
I think the moment Winston died was when he was in room 101. O’Brian and the party caused Wilsons death. When he put the rats around his head and got him to go against Julia, he killed him. Winston came out of that room as a new person. When he saw Julia he didn’t even act like his old self. He acted like their relationship didn’t mean anything anymore. His love for her and his life was taken in room 101. So I think he did die inside even though his body was still alive.