Cardanol (3-pentadecenyl-phenol), a well-known non-edible natural oil obtained as a by-product of the Cashew Industry, represents a valid alternative to petro-based derivatives, thanks to its peculiar chemical structure. When selected as raw material in the synthesis of epoxy curing agents or polyols and diols for polyurethane applications, cardanol can impart unique benefits, like chemical resistance, hydrolytic stability, thermal resistance, and balanced mechanical properties. However, there are applications and sectors where the use of cardanol is still quite limited or not fully exploited, due to lack of suitable building block derivatives. In this Paper, the synthesis of novel cardanol-derived cyclohexene obtained by full hydrogenation of cardanol and subsequent dehydration of the resulting 3-pentadecyl-cyclohexanol into 3-pentadecyl-cyclohexene and 4-pentadecyl-cyclohexene as a mixture of isomers will be presented, along with some preliminary examples of their functionalization into a variety of potential reactive monomers and polymer building blocks.