Anne of Windy Poplars takes place over the three years between Anne's graduation from Redmond College and her marriage to Gilbert Blythe. While Gilbert is in medical school, Anne takes a job as the principal of Summerside High School, where she also teaches. She lives in a large house called Windy Poplars with two elderly widows, Aunt Kate and Aunt Chatty, along with their housekeeper, Rebecca Dew, and their cat, Dusty Miller.