The 1,3-benzodioxol moiety present in safrole, apiole, and myristicin essential oils and benzodioxol derivatives have shown a wide range of biological activities including antiepileptic, analgesic, antituberculosis, and antimicrobial potentials. Here, we have tested the antibacterial and antioxidant activities of a series of benzodioxol derivatives. Twelve compounds of aryl acetate and acetic acid benzodioxol were evaluated against different types of bacterial strains, including Staphylococcus aureus, Escherichia coli, Enterococcus faecalis, and Pseudomonas aeruginosa using the broth dilution method, and the most potent compound was 3e, which exhibited the bacterial growth of with MICs of 125 (S. aureus), 250 (E. coli), 220 (E. faecalis), and 100 µg/mL (P. aeruginosa). Our positive control, cinoxacin, had MICs of 250 (S. aureus), 250 (E. coli), 250 (E. faecalis), and 500 µg/mL (P. aeruginosa). Antioxidant activity was evaluated for the synthesized compounds utilizing the DPPH assay. The 3a compound was the most active with an IC50 value of 21.44 µg/mL, while the IC50 values of compounds 3b, 3e, and 3f were 96.07, 58.45, and 72.17 µg/mL, respectively. In contrast, all compounds with the acetic acid functional group had weaker activity, with an IC50 range of 193.52–289.78 µg/mL compared with the potent antioxidant agent Trolox (IC50 = 1.93 µg/mL). In the present paper, new benzodioxol-based aryl acetate and acetic acid derivatives were evaluated for their antibacterial and antioxidant activities. The outcomes revealed that the antibacterial and antioxidant properties of some of the synthesized benzodioxol aryl acetate and acetic acid derivatives can be considered as valuable materials for the pharmaceutical industry. Thus, these molecules should be further evaluated in vivo as lead compounds for the discovery of new drug candidates.