Background: Hypertension and LDL hypercholesterolemia often coexist, and their effective treatment has favorable implications for cardiovascular health. We aimed at defining the impact of amlodipine and rosuvastatin as free or fixed combinations on blood pressure (BP) and LDL-cholesterol, and the satisfaction with treatment, in hypertensive individuals with LDL hypercholesterolemia. Methods: A spontaneous longitudinal observational study was conducted at Italian cardiology outpatients clinics. Eligible individuals (age ≥ 18y, informed consent, stable 5 or 10 mg amlodipine therapy in addition to a RAAS inhibitor, stable 10 or 20 mg rosuvastatin therapy) underwent home and office BP and LDL-cholesterol assessment at 12 and 24 weeks. BP and LDL-cholesterol control rates and satisfaction with the fixed combination were assessed. Results: 285 participants were enrolled (51%M; 67 ± 10y; 94 on the free combination). At 12 weeks, mean BP and LDL-cholesterol were reduced in both groups, with higher hypertension control rates in the fixed combination group; at 24 weeks they were further reduced compared with baseline, and home systolic BP was lower in the fixed than the free combination group (121.9 ± 17.6 vs 129.4 ± 8.5 mmHg; p = 0.03). Patients in the fixed combination reported higher satisfaction with this regimen than with the free combination. Conclusions: The fixed combination of calcium channel blocker and statin appears to have advantages in terms of clinical efficacy and patients’ satisfaction.