It is true that in many stories that are fan fiction, Winston is one of the Heirs of Slytherin. This was not described in the original Harry Potter book series.
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The same as it means in real life, the heir is the next in line to something. In the context of the heir of Slytherin, it means someone from Slytherin's bloodline who had the same affinity for snakes.
Answer: No. Voldemort was stronger. He was the strongest wizard known to wizard kind aside from Dumbledore. Answer: Most likely, but one couldn't tell for sure, because Slytherin lived a thousand years before Voldemort. (Note: Voldemort was very proud to be Slytherin's Heir.)
Answer (1): No, Harry Potter is not a prince but he is heir of gryffindor and magical heir of slytherin. Answer(2): (Spoiler alert!) The "prince" in Harry Potter 6 is equivalent to Severus Snape. Answer to answer (2) - in this Severus was half blood prince not prince.
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There is no person, ghost, or portrait that guards the Slytherin common room (actually called Slytherin Dungeon). It is hidden behind a wall, and a password must be spoken to the wall in order for it to move aside.