In previous studies, after regularly consuming a green/roasted coffee blend, body weight, body fat%, glucose, plasminogen activator inhibitor-1 (PAI-1), resistin, leptin, ghrelin, diastolic (DBP) and systolic blood pressure (SBP) significantly changed in healthy and hypercholesterolemic subjects. However, glucagon, total-cholesterol (T-C), triglycerides (TG), LDL-cholesterol (LDL-C) and Homeostasis Model Assessment index to estimate insulin resistance (HOMA-IR) only changed in the hypercholesterolemics. This work looks into the antiobesity effects of coffee blend and into the relationship of antiobesity with the aforementioned cardiometabolic modifications in hypercholesterolemics. (1) Methods: Tricipital and subscapular skinfolds, hip, thigh, arm and waist circumference (WC) were measured in normocholesterolemic and hypercholesterolemics. To understand the relationship between cardiometabolic and antiobesity results in hypercholesterolemics, factor analysis was carried out using baseline values of the variables that changed. (2) Results: WC, WC/hip and WC/height showed significant coffee×group interaction, and in hypercholesterolemics tended to decrease. After factor analysis, three factors emerged, accounting for 29.46, 13.13 and 11.79% of variance. Only factor 1 (main loadings: WC, DBP and SBP, body weight, WC/hip and WC/height ratios, TG and ghrelin, inversely) decreased after coffee intake. (3) Conclusion: Regularly consuming green/roasted coffee may help to control body weight, and in hypercholesterolemics, may reduce cardiovascular risk by reducing abdominal adiposity and blood pressure.