Purpose: To elucidate the management of individuals with chronic retinal detachment, considering both surgical intervention and observation. The authors specifically focus on the long-term anatomical and functional outcomes, with a particular emphasis on optical coherence tomography follow-up. Methods: Data from 24 consecutive patients presenting with a chronic retinal detachment between 2014 and 2023 at the Department of Ophthalmology and Optometry, Medical University of Vienna, Austria, were retrospectively analyzed. The study used optical coherence tomography scanning with the Heidelberg Spectralis optical coherence tomography device's integrated measurement tool to assess the stability of chronic retinal detachment, potentially introducing optical coherence tomography as a follow-up tool for these patients. Results: The study included 27 eyes of 24 patients with an average age of 41.8 ± 13 years, and the mean follow-up time was 34 ± 27 months. Among the cases, 11 (41%) progressed and required surgery. Of these surgeries, 4 (37%) were scleral buckling and 7 (63%) were pars plana vitrectomy. After surgery, 64% experienced improved or stable vision, whereas 36% experienced a decrease in visual acuity. In the subgroup that had pars plana vitrectomy, two eyes (29%) had a redetachment, necessitating a second surgery. Meanwhile, 94% of untreated patients maintained stable 20/20 best-corrected visual acuity throughout the entire follow-up period. Conclusion: A cautious observation strategy could lead to superior outcomes when contrasted with more invasive management approaches in patients with chronic retinal detachment. Furthermore, when surgical intervention becomes imperative, the study suggests a preference for the adoption of a scleral buckling procedure in phakic patients without posterior vitreous detachment.