A crude hydromethanolic extract from Pinus brutia bark and its fractions (diethyl ether, ethyl acetate, n-butanol, and aqueous fractions) were studied with regard to their phenolic content and antioxidant activities. The total phenolics and proanthocyanidins in each extract were quantified by spectrophotometric methods; the polyphenolic profile was analyzed by RP-HPLC-DAD-ESI-MS. All extracts were tested with regard to their ability to scavenge free radicals (ABTS radical cation, superoxide and hydroxyl radicals), reduce ferric ions, and inhibit 15-lipoxygenase. P. brutia bark extracts had high phenolic contents ($303.79{pm}7.34$-$448.90{pm}1.39$ mg/g). Except diethyl ether extract, all other extracts contained proanthocyanidins ranging from $225.79{pm}3.94$ to $250.40{pm}1.44$ mg/g. Several polyphenols were identified by RP-HPLC-DAD-ESIMS: taxifolin in diethyl ether extract, a taxifolin-O-hexoside, catechin, procyanidin dimers, and trimers in ethyl acetate extract. Except diethyl ether extract, all other extracts were effective scavengers of superoxide and hydroxyl radicals ($EC_{50}$ = $33.5{pm}1.1$-$54.93{pm}2.85{mu}g/mL$ and $0.47{pm}0.06$-$0.6{pm}0.0mg/mL$, respectively). All extracts had noticeable 15-lipoxygenase inhibitory effects ($EC_{50}$ = $22.47{pm}0.75$-$34.43{pm}2.25{mu}g/mL$). We conclude that P. brutia bark is very promising for the dietary supplements industry due to its high free radical scavenging and 15-lipoxygenase inhibitory effects.