Surgical treatment of infective endocarditis (IE) remains challenging, especially in cases of perivalvular destruction and poor clinical presentation. We evaluated the outcomes of surgery for simple (isolated leaflet involvement) versus complex (perivalvular involvement) primary left-sided native valve endocarditis. From 2005 to 2019, a total of 128 consecutive patients (age 57.7 ± 14.2 years) with IE were surgically managed. Study end points were operative and late mortality and freedom from recurrent infection and reoperation for recurrent endocarditis. Patients were categorized as having simple IE (n = 91) versus complex IE (n = 37) based on the preoperative imaging and/or intraoperative findings. Valves involved were aortic in 39% (n = 50), mitral in 46% (n = 59), or both (11%, n = 14). The operative mortality was 11.7% (n = 15), and 9 of them (60%) presented with shock or multiorgan failure. A critical preoperative state was the only independent risk factor for early mortality (odds ratio 7.43, p <0.01). The overall survival was 81.9%, 74.8%, 58%, and 52% at 1, 5, 10, and 15 years, respectively. Long-term survival was similar between simple and complex groups (p = 0.29). Chronic renal failure was the only independent risk factor for late mortality (hazard ratio 2.44, p = 0.02). Freedom from re-endocarditis was 95.2%. None of the patients underwent reoperation because of recurrent endocarditis. Mitral valve repair was performed in 30.7% of all cases with mitral valve involvement. None of them had significant mitral regurgitation or recurrent endocarditis on follow-up. In conclusion, surgery for IE in the setting of complex perivalvular involvement is associated with a low rate of recurrent endocarditis or reoperation and comparable long-term survival to patients with isolated leaflet involvement. Mitral valve repair was feasible and durable in a significant proportion of patients even in the presence of endocarditis.