Polyphenols are natural compounds from plants and are relevant in terms of quality. Procyanidins, also known as condensed tannins, are oligo and polymeric polyphenols that contribute to the organoleptic properties of some beverages, especially by their astringency and bitterness. They are known to bind food macromolecules, proteins and carbohydrates, by non-covalent interactions; procyanidins with high degree of polymerization are adsorbed onto cell walls. In grape, binding of procyanidins to grape skin has been shown to vary with maturity. The astringency of perry pear juice depends heavily on the fruit maturity, with over-ripening practices being commonly used for production of perry. The phenolic profile of perry pear parenchyma is very simple, mainly caffeoylquinic acid and procyanidins, the later being high polymerized and based on (−)-epicatechin units. The aim of the present work was to characterize the phenolic composition and content of pear juices and to report differences that occur depending of the maturity stage of the fruits. Juices were extracted from two perry pear cultivar ’De Cloche’ and ‘Plant de Blanc’ from ripe and overripe fruits.The polyphenols were analyzed in the fruit, in the juice, and in the pomace by HPLC-DAD. Procyanidins contents and compositions remained stable during the over-ripening of pears. In the juice, the procyanidins concentration varied with the maturity stage during fruit pressing. The extraction of procyanidins in the juice was largely limited by formation, spontaneously, of non-covalent adducts, via hydrogen bonding and hydrophobic effects, with pear cell walls.