The development of epoxy thermosets from renewable resources is of paramount importance in a sustainable development context. In this paper, a novel bio-based epoxy monomer derived from limonene was synthesized without epichlorohydrine and characterized. In fact, this paper depicts the synthesis of bis-limonene oxide (bis-LO). However, intern epoxy rings generally exhibit a poor reactivity and allow reaction with anhydride. Therefore, we used a reaction model with hexahydro-4-methylphthalic anhydride to compare reactivity of terminal and interepoxy functions. We also studied the influence of methyl group on intern epoxy functions. Furthermore, the influence of epoxy:anhydride stoichiometry and initiator amount was studied. These studies allow to propose an optimized formulation of bis-LO. Finally, a bis-LO-based thermoset was obtained and characterized.