Nowadays as environmental concerns have became so significant, new reactions and novel catalysts for complicated chemistry are still in high demand despite tremendous advances accomplished through developing cheaper and more versatile chemical catalysts and optimizing the reaction media. As a large number of natural products and synthetic molecules, used as drugs or pharmacological agents, contain a 1,3-diol moiety either in a syn or anti relationship, the development of new protocols utilizing biocatalysts/chemocatalysts for the stereoselective synthesis of 1,3-diols continues to be of great interest in organic chemistry. In this review, we seek to highlight the efforts made in the past 12 years towards the enzyme-catalyzed synthesis of chiral 1,3-diols, though special attention is also paid to one-pot strategies where several reactions are conducted sequentially in the same reaction vessel, without the isolation of intermediates.