Anne of Windy Poplars tells about the three years between Anne’s graduation from Redmond College and her marriage to Gilbert Blythe. Anne has taken a job as the principal at Summerside High School, where she also teaches geometry.

She lives in a large boardinghouse called Windy Poplars with two elderly widows, Aunt Kate and Aunt Chatty, plus their housekeeper, Rebecca Dew, and their cat, Dusty Miller. During her time in Summerside, Anne must learn to manage many of Summerside’s inhabitants, including the clannish and resentful Pringle family, her bitter colleague Katherine Brooke, and others of Summerside’s more eccentric residents.

Additionally, Anne befriends the young and lonely girl, Elizabeth Campbell, who lives next door to Windy Poplars. At the end of the novel, Anne departs Summerside, returning to Green Gables and Avonlea for her wedding to Gilbert.