Generation of renewable polymers is a long-standing goal toward reaching a more sustainable society . Herein we show how conceptually simple oxidative transformations can be used to unlock the inherent reactivity of terpene synthons in generating polyesters by two different mechanisms starting from the same α-pinene substrate. In the first pathway, α-pinene was oxidized into the bicyclic verbanone based lactone (VaL) and subsequently polymerized into star-shaped polymers via ring-opening polymerization, resulting in a biobased semicrystalline polyester with tunable glass transition and melting temperatures In a second pathway, polyesters were synthesized via polycondensation, utilizing the diol (1-(1'-hydroxyethyl)-3-(2'-hydroxyethyl)-2,2-dimethylcyclobutane (HHDC)) synthesized by oxidative cleavage of the double bond of α-pinene, together with unsaturated biobased diesters such as di-Me maleate (DMM) and di-Me itaconate (DMI), resp. The resulting families of terpene-based polyesters were thereafter successfully crosslinked by either transetherification, utilizing the terminal hydroxyl groups of the synthesized verbanone-based materials, or by UV-irradiation, utilizing the unsaturation provided by the DMM or DMI moieties within the HHDC-based copolymers. This work highlights the potential to apply an oxidative toolbox to valorize inert terpene metabolites enabling generation of bio sourced polyesters and coatings thereof by complementary mechanisms.