Functional food consumption is shown to have a positive effect on anthropometric parameters and human health promotion. In addition, consumers seem to be more interested in food choices, that may have a positive effect on their health. The current study aimed to identify the antioxidant and phenolic content of naturally functional foods from the Mediterranean diet and to investigate consumer behavior towards their consumption in terms of their weight control, as well as their purchasing behavior and knowledge of functional foods. For this purpose, blueberries, cranberries, pomegranate, grapefruit, red peppers, almonds and mountain tea were analyzed for their phenolic content and antioxidant capacity, using the Folin-Ciocalteau and Ferric Reducing Antioxidant Power assays, respectively. Furthermore, nine hundred forty-nine healthy Greek adults participated in an epidemiological study, by completing a validated food frequency questionnaire, for the consumption of the above investigated functional foods. Five hundred and fifty participants also completed an online questionnaire investigating factors that consumers evaluate when purchasing functional foods. Study results showed that the analyzed functional foods were high in antioxidants and phenolic compounds, especially the mountain tea. The increased consumption of cranberries, pomegranate, grapefruit, red peppers and mountain tea was significantly correlated with a decreased Body Mass Index, suggesting a possible positive role, in weight control. Participants seemed to be aware of the beneficial role of these specific investigated Mediterranean functional foods to human health. They evaluated the price, taste and nutritional value, as critical factors to buy these food products. A combination of factors seems to lead them to purchase and consume these functional foods. Future epidemiological and clinical studies should be conducted in order to further evaluate consumer preferences and bioactivity mechanisms related to Mediterranean functional food consumption.