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St. John’s wort (<i>Hypericum perforatum</i>, Hypericaceae) has long been used in traditional medicine as a potent remedy, while many other species of this genus have not been thoroughly investigated. The study aimed to detect the biological activity, including antioxidant, antihyperglycemic, anticholinergic, antimicrobial and monoaminoxidase inhibitory potential, of water-alcoholic extracts of three species autochthonous for Serbia and Greece from plant genus <i>Hypericum</i> (section <i>Hypericum</i>—<i>H. tetrapterum</i>, <i>H. maculatum</i> ssp. <i>immaculatum</i> and <i>H. triquetrifolium</i>), followed by phytochemical profiling. The highest amount of phenolics was recorded in <i>H. maculatum</i> subsp. <i>immaculatum</i> extract, while the highest abundance of flavonoids was characteristic of <i>H. tetrapterum</i> extract. Hypericin and hyperforin, quercetin, and its flavonoid, rutin, were present in all of the evaluated species. The evaluated species were good scavengers of DPPH, OH and NO radicals, as well as potent reducers of ferric ions in FRAP assay. Furthermore, the evaluated species were shown as potent inhibitors of monoaminoxidase A and α-glucosidase and modest inhibitors of acetylcholinesterase, monoaminoxidase B and α-amylase. No anti-Candida activity was recorded, but the extracts were effective against MRSA <i>Staphylococcus aureus</i> and <i>Enterococcus</i> sp., as well as against <i>Proteus mirabilis</i>. The obtained results strongly highlight the need for further in vivo studies in order to better define the potential of the medicinal application of the studied species.