Background: Diabetic retinopathy (DR) is a leading cause of visual impairment globally among working-aged individuals. This study aims to update data on DR prevalence in Bulgaria. Methods: The present cross-sectional study was conducted between 1 January 2022 and 1 January 2023, using a local diabetes registry from the city of Varna as a sampling framework. In total, 587 diabetic patients underwent DR examination. Data included demographics, diabetes type/duration, treatment, and ophthalmic history. DR status was assessed using indirect slit-lamp biomicroscopy or digital fundus photography, graded by the International Clinical Diabetic Retinopathy Scale. Results: Of 587 participants, 13 were excluded due to cataract-related ungradable images. The median age was 65 years (IQR 56–73), with a slight female predominance (54%). The overall prevalence of any DR was 39.9% (95% CI 35.9–44.0), with non-proliferative DR (NPDR) at 27.5%, proliferative DR (PDR) at 7.3%, and macular edema (DME) at 5%. Type 1 diabetes patients had significantly higher DR prevalence (68.8%) than type 2 (34.1%, p < 0.001). Men exhibited higher DR prevalence. Age and diabetes duration correlated positively with DR prevalence. Insulin treatment was associated with higher DR prevalence (55.6%) than oral antidiabetic treatment (22.5%, p < 0.001) for type 2 diabetes patients. Among those diagnosed with DR, 70.9% received treatment, mainly laser therapy. Conclusions: These findings provide epidemiological insights for future research and emphasize the need for a comprehensive national DR screening program in Bulgaria. Technological advancements enable proactive measures to mitigate DR-related visual impairment and blindness, including widespread screening, even in rural areas.