Raspberries are rich in phenolic phytochemicals. To study the health benefits of raspberries, four fresh raspberry varieties (Heritage, Kiwigold, Goldie, and Anne) were evaluated for total antioxidant and antiproliferative activities. The total amount of phenolics and flavonoids for each of the four raspberry varieties was determined. The Heritage raspberry variety had the highest total phenolic content (512.7 ± 4.7 mg/100 g of raspberry) of the varieties measured followed by Kiwigold (451.1 ± 4.5 mg/100 g of raspberry), Goldie (427.5 ± 7.5 mg/100 g of raspberry), and Anne (359.2 ± 3.4 mg/100 g of raspberry). Similarly, the Heritage raspberry variety contained the highest total flavonoids (103.4 ± 2.0 mg/100 g of raspberry) of the varieties tested, followed by Kiwigold (87.3 ± 1.8 mg/100 g of raspberry), Goldie (84.2 ± 1.8 mg/100 g of raspberry), and Anne (63.5 ± 0.7 mg/100 g of raspberry). The color of the raspberry juice correlated well to the total phenolic, flavonoid, and anthocyanin contents of the raspberry. Heritage had the highest a/b ratio and the darkest colored juice, and the Anne variety showed the lowest phytochemical content and the palest color. Heritage raspberry variety had the highest total antioxidant activity, followed by Kiwigold and Goldie, and the Anne raspberry variety had the lowest antioxidant activity of the varieties tested. The proliferation of HepG2 human liver cancer cells was significantly inhibited in a dose-dependent manner after exposure to the raspberry extracts. The extract equivalent to 50 mg of Goldie, Heritage, and Kiwigold fruit inhibited the proliferation of those cells by 89.4 ± 0.1, 88 ± 0.2, and 87.6 ± 1.0%, respectively. Anne had the lowest antiproliferative activity of the varieties measured but still exhibited a significant inhibition of 70.3± 1.2% with an extract equivalent to 50 mg of fruit. The antioxidant activity of the raspberry was directly related to the total amount of phenolics and flavonoids found in the raspberry (p < 0.01). No relationship was found between antiproliferative activity and the total amount of phenolics/flavonoids found in the same raspberry (p > 0.05).