Lehane was born and raised in the Dorchester neighborhood of Boston, Massachusetts. He lived in the Boston area most of his life, where he sets most of his books, but now lives in southern California. He spent summers on Fieldston Beach in Marshfield. Lehane is the youngest of five children. His father was a foreman for Sears & Roebuck, and his mother worked in a Boston public school cafeteria. Both of his parents emigrated from Ireland. Lehane is a graduate of Eckerd College in St. Petersburg, Florida.
His brother, Gerry Lehane, who is two and a half years older than Dennis, trained at the Trinity Repertory Company in Providence and became an actor in New York in 1990. Gerry is a member of the Invisible City Theatre Company.
Lehane is married to Chisa Lehane. He has two children from a previous marriage.

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