The title comes from a story in which Winnie-the-Pooh and Piglet build a house for Eeyore. In another story the game of Poohsticks is invented. As with the first book, the chapters are mostly in episodic format and can be read independently of each other. The only exception to this is with Chapters 8 and 9 - Chapter 9 carries directly on from the end of Chapter 8, as the characters search for a new house for Owl, his house having been blown down in the previous chapter.

Hints that Christopher Robin is growing up, scattered throughout the book, come to a head in the final chapter, in which the inhabitants of the Hundred Acre Wood throw him a farewell party after learning that he must leave them soon. It is made obvious, though not stated explicitly, that he is starting school. In the end, they say good-bye to Christopher Robin. Pooh and Christopher Robin say a long, private farewell, in which Pooh promises not to forget him.