You may notice a bit of a disconnect with chapter fourteen.
Caleb is given the land of Hebron, where the Anakites live. But we have previously been told that no Anakites were left in Israelite territory (11:22). How can this be?
Caleb receives his land at age 85, less than five years after entering Canaan. And yet, the text says that Joshua and his forces waged war for a very long time (11:18) – certainly longer than five years. The point here is that Joshua is not laid out in strict chronological fashion. The land is conquered in chapters 9 – 11, but some of what you find, like this reference, occurs during that conquest period, not after it.
Also, keep in mind the flow of this book.
Chapters 9 – 11 deal with the land’s conquest, beginning with the south and moving to the north. Chapter 13 deals with the division of the land east of the Jordan. Chapters 14-19 the division of the land west of the Jordan.
Why so much space given to the division of the land? Probably to make the certain point that all of God’s promises regarding the land came true – a fact emphasized three times in chapters 21 – 23.