Anoles regularly get transported on tropical plants grown in Florida to all over North America. Unless they end up inside a greenhouse that has lots of bugs, they can’t survive the winter in Canada. From what I can tell from clicking on random observations, their northern extent is probably somewhere around the North Carolina/Virginia border since most observations north of there have discussions about provenance. There have been lots of discussions about whether they count as wild or not and consensus is to call them wild.
For interest’s sake, in birding rules if it travelled from a wild population without intentional human help then an anole in Ontario would “count”, but an escaped pet would not. By iNat rules both are “countable”.
A couple more related papers:
https://www.authorea.com/users/802604/articles/1187343-disentangling-complex-biological-introduction-histories-the-ongoing-invasion-of-the-brown-anole-anolis-sagrei
https://www.academia.edu/2143041/Climate_niche_shift_in_invasive_species_the_case_of_the_brown_anole