Chiral nitrogen-containing heterocyclic alcohols are a group of important organic compounds and have been widely applied as building blocks of various synthetic pharmaceuticals and natural bioactive compounds. Herein, we summarized the chemical and enzymatic methods for the synthesis of chiral nitrogen-containing heterocyclic alcohols. Particularly, the enzymatic approaches for the asymmetric synthesis of chiral piperidinol, quinuclidinol and pyrrolidinol were introduced and discussed.