A novel series of triazole alcohol antifungals bearing a 5-benzoylbenzimidazol-2-ylthio side chain have been designed and synthesized as hybrids of fluconazole (a typical triazole antifungal) and mebendazole (an anthelmintic agent with antifungal activity). The title compounds were synthesized via the reaction of an appropriate oxirane and desired 2-mercaptobenzimidazole. Although there was possibility for formation of different N-substituted or S-substituted products, the structures of final compounds were assigned as thioether congeners by using 13C NMR spectroscopy. The SAR analysis of the primary lead compounds (series A) was conducted by simplifying the 5-benzoylbenzimidazol-2-ylthio residue to the benzimidazol-2-ylthio (series B) or benzothiazol-2-ylthio side chain (series C), and modification of halogen substituent on the phenethyl-triazole scaffold. In general, series A (compounds 4a-e) containing 5-benzoylbenzimidazole scaffold showed better antifungal activity against Candida spp. and Cryptococcus neoformans than related benzimidazole and benzothiazole derivatives. The better results were obtained with the 4-chloro derivative 4b displaying MICs <0.063–1 μg/mL. Although, removing benzoyl group from compound 4b had negative effect on the activity, optimization of phenethyl-triazole scaffold by desired halogen substituent resulted in compound 5c being as potent as 4b. In vitro and in silico ADMET evaluations of the most promising compounds 4b and 5c indicated that the selected compounds have desirable ADMET properties in comparison to standard drug fluconazole. Docking simulation study demonstrated that the benzimidazol-2-ylthio moiety is responsible for the potent antifungal activity of these compounds.