Background: The epidemiological evidence for a relation between dietary polyphenol intake and depression is limited. Therefore, the aim of this study was to assess the association between habitual dietary intake of total polyphenols, their classes, subclasses and individual compounds and depressive symptoms among the participants of the Mediterranean healthy Eating, Lifestyle and Aging (MEAL) study. Methods: Demographic and dietary characteristics of 1572 adults living in southern Italy were analyzed. Food frequency questionnaires and Phenol-Explorer were used to calculate habitual dietary intakes of polyphenols. The Center for Epidemiologic Studies Depression Scale (CES-D-10) was used as screening tool for depressive symptoms. Multivariate logistic regression analyses were used to test associations and were expressed as odds ratio (OR) and 95% confidence intervals (CI). Results: A total of 509 individuals reported having depressive symptoms. Based on multivariate logistic regression analyses, total polyphenol intake was not associated with depressive symptoms. After adjustment for potential confounding factors, dietary intake of phenolic acid (OR = 0.64, 95% CI: 0.44, 0.93), flavanones (OR = 0.54, 95% CI: 0.32, 0.91), and anthocyanins (OR = 0.61, 95% CI: 0.42, 0.89) showed significant inverse association with depressive symptoms, when comparing the highest with the lowest quartile. Moreover, flavanones and anthocyanins, were associated with depressive symptoms in a dose-response manner. Among individual compounds, inverse association was observed for quercetin (OR = 0.53, 95% CI: 0.32, 0.86) and naringenin (OR = 0.51, 95% CI: 0.30, 0.85), for the highest versus lowest quartile of intake. When taking into consideration the major sources of the polyphenols, only citrus fruits and wine consumption was inversely associated with depressive symptoms (Q4 vs. Q1: OR= 0.51, 95% CI: 0.35, 0.75; Q4 vs. Q1: OR = 0.53, 95% CI: 0.38, 0.74, respectively). Conclusions: Higher dietary intake of flavonoid may be inversely associated with depressive symptoms. Further studies are needed to definitively confirm these observed associations.