Chiral cyclic and heterocyclic alcohols are important structural units for fine chemicals, agrochemicals, and chiral pharmaceuticals such as ladostigil, imbruvica, and sulopenem. Natural enzymes show low affinity toward molecules harboring bulky substituents or similarly-sized substituents on the ring. Thus, engineered enzymes represent an alternative option for the biosynthesis of chiral cyclic and heterocyclic alcohols. This review covers the recent progress in various biological approaches applied to the synthesis of enantiomerically pure cyclic and heterocyclic alcohols, including enzymatic asymmetric reduction of the CO bond, asymmetric hydroxylation of the C–H bond, and asymmetric hydrolysis reaction of the C–O bond. This review gathers relevant theoretical and experimental clues for organic synthesis of chiral cyclic and heterocyclic alcohols.