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, plus their housekeeper, Rebecca Dew, and their cat, Dusty Miller. This book follows Anne from the age of 22 to 25.