The 2,3-dihydrobenzofuran heterocyclic systems are found in various biologically active natural and pharmaceutical products of biological relevance such as Phalarine, Rocaglamide, and Furaquinocin A. The interest in the study of 2,3-dihydrobenzofurans is constantly increasing because of their numerous biological properties such as anti-tumor, anti-cancer, anti-tubercular, and anti-malarial activities. Different methods have been established towards the synthesis of 2,3-dihydrobenzofurans involved via intra- and inter-molecular reactions. Besides, the 1,3-dihydroisobenzofuran structure has been identified as a fundamental nucleus in many natural products, bioactive compounds, and functional molecules (e. g., Pestacin, Isopestacin, Citalopram, Xylarinol B, Matriisobenzofuran, Thunberginol F7-O-β-D-glucopyranoside). On the other hand, 1,3-disubstituted isobenzofurans are powerful structural motifs with a wide range of biological activities, like anti-inflammatory, anti-histaminic, and anti-HIV. In the last few years, a decent number of diligent synthetic approaches have been demonstrated toward synthesizing 1,3-disubstituted isobenzofurans. This review focuses on the effective synthetic routes developed to construct 2,3-dihydrobenzofurans and 1,3-dihydroisobenzofurans and their applications in recent years. © 2022 Wiley-VCH GmbH.