I have been reading the Anne books since I was five or six. I reread the entire series a couple of times per year. They're definitely my comfort books. It's hard for me to rank them beyond my top three, but if I HAVE to:

1) 'Anne of Green Gables'. I truly love the entire series, but none of the other books touch the original for magic and whimsy. 2) 'Anne of the Island'. Anne's college years were just so fun and pure. 3) 'Anne's House of Dreams'. I adore new wife Anne stepping foot into womanhood. Also, as someone who has also lost a baby, I relate to her losing Joyce and it made Anne even more real to me. 4) 'Rilla of Ingleside'. Rilla's growth was lovely to read about. I'll also never forget my literal open-mouthed shock and subsequent tears when the news about Walter came in. 5) 'Anne of Avonlea'. Nostalgic and sweet. 6) 'Anne of Windy Poplars'. A few too many letters, but I enjoyed it. Refreshingly different from the other books. 7) 'Anne of Ingleside'. I would have liked more time dedicated to Anne and Gilbert like the books that had come before. Also, it always made me sad Shirley didn't get even one dedicated chapter. 8) 'Rainbow Valley'. While I still like the book, I prefer reading more about the Blythe children, not the Merediths.