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<i>Epilobium</i> species are used in Romanian folk medicine as tinctures, tea, or tablets for ameliorating the symptoms of benign prostate hyperplasia (BPH), but scientific-based evidence is scarce for this species or other endemic plants of the same genus. Therefore, the aims of this research were to evaluate the phytochemical profile of five endemic <i>Epilobium</i> species (<i>E. hirsutum</i> L., <i>E. parviflorum</i> Schreb., <i>E. palustre</i> L. <i>E. dodonaei</i> Vill., and <i>E. angustifolium</i> L.) and to assess their in vitro biological activity. For enhanced recovery of polyphenols, a D-optimal experimental plan was developed using Modde software and the optimal working conditions were ultra-turrax-assisted extraction, for 8 min, with 30% ethanol in water. The optimized extracts were obtained from various plant parts and were further characterized by LC-MS analysis, with the major compound being oenothein B. All extracts demonstrated good antioxidant activity, evaluated by DPPH and TEAC assays. The most prominent antimicrobial potency of optimized extracts was displayed against <i>Bacillus cereus</i>, while against Gram-(+) bacteria, a moderate efficacy was observed. Furthermore, anti-cancer, anti-inflammatory, and antioxidant potential were assessed on normal fibroblasts and prostate carcinoma cell lines. From the evaluated optimized extracts, <i>E. angustifolium</i> aerial parts had the highest selectivity toward killing cancerous cells, followed by <i>E. hirsutum</i> aerial parts extract. For the antioxidant effect, <i>E. hirsutum</i> leaves and <i>E. hirstum</i> aerial parts extracts displayed the highest potency, decreasing ROS at the level observed for the positive control. The highest anti-inflammatory potential, based on the IL-6 and IL-8 levels, was displayed by <i>E. dodonaei</i> aerial parts and <i>E. angustifolium</i> leaves extracts. In conclusion, all five endemic species of <i>Epilobium</i> harvested from Romanian flora possess a diverse phytochemical composition, which supports complex biological activities.