A comparative study of volatiles, antioxidant activity, phytotoxic activity, as well as in silico molecular docking and ADMET study, was conducted for essential oils from three Vitex species, viz., V. agnus-castus, V. negundo, and V. trifolia. Essential oils (OEs) extracted by hydrodistillation were subjected to compositional analysis using GC-MS. A total number of 37, 45, and 43 components were identified in V. agnus-castus, V. negundo, and V. trifolia, respectively. The antioxidant activity of EOs, assessed using different radical-scavenging (DPPH, H₂O₂ and NO), reducing power, and metal chelating assays, were found to be significant as compared with those of the standards. The phytotoxic potential of the EOs was performed in the receptor species Raphanusraphanistrum (wild radish) and the EOs showed different levels of intensity of seed germination inhibition and root and shoot length inhibition. The molecular docking study was conducted to screen the antioxidant and phytotoxic activity of the major and potent compounds against human protein target, peroxiredoxin 5, and 4-hydroxyphenylpyruvate dioxygenase protein (HPPD). Results showed good binding affinities and attributed the strongest inhibitory activity to 13-epi-manoyl oxide for both the target proteins.