Introduction: Stapes surgery is a safe procedure, with favourable hearing outcome. The objective of the study is to assess the long-term hearing results, addressing the bone conduction (BC) decay and the need for hearing aids in otosclerosis patients. Methods: We enrolled patients who underwent stapes surgery by means of stapedectomy or stapedotomy between 1991 and 2001. All enrolled patients underwent pure-tone audiometry (PTA) between September 2017 and June 2018. A set of questions was administered to record the prevalence of subjective symptoms and the need for hearing aids. Results: Seventy patients were enrolled for a long-term evaluation; 37 patients underwent bilateral surgery; therefore, 107 ears were included in the analysis. The average follow-up period was 22 years. No statistically significant difference was found between early and late post-operative air conduction (AC) PTA (41 vs. 49 dB; p > 0.05) nor between early and late post-operative BC-PTA (29 vs. 37 dB; p > 0.05). A significant difference was observed for AC at 8 kHz (65 vs. 78 dB; p < 0.05) and BC at 2 and 4 kHz (28 vs. 40 dB and 45 vs. 58 dB, respectively; p < 0.05). Conclusions: This is, to our knowledge, the longest mean follow-up time in the literature. A mild decrease in both AC and BC threshold can be expected and the sensorineural decay is more pronounced on the high frequencies. The subjective hearing symptoms and overall sound perception are satisfactory.