On the question of whether dragons survived into the Fourth Age, we have Tolkien's words from Letter 144:
"Some stray answers. Dragons. They had not stopped; since they were active in far later times, close to our own. Have I said anything to suggest the final ending of dragons? If so it should be altered. The only passage I can think of is Vol. I p. 70: 'there is not now any dragon left on earth in which the old fire is hot enough'. But that implies, I think, that there are still dragons, if not of full primeval stature."
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'They say,' answered Andreth: 'they say that the One will himself enter into Arda, and heal Men and all the Marring from the beginning to the end.'
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