A series of six-membered bicyclic carbonates has been prepared from an alcohol precursor through esterification, etherification and silyl-etherification methods to afford functional monomers with synthetically useful vinyl, allyl, alkynyl and polymerizable groups that allow for orthogonal polymerization strategies. Anionic ring-opening polymerization (AROP) of these monomers allows us to access densely functional aliphatic polycarbonates with M_n‘s and T_g‘s in the range of 3.2–11.7 kg mol⁻¹ and 11–106 °C, respectively. Bifunctional monomers comprising two separate polymerizable groups can be selectively polymerized via AROP or radical based/ring-opening metathesis polymerization methods. Selected polycarbonates were post-modified via thiol–ene chemistry to further modulate their properties. Finally, base-mediated depolymerization of these new polycarbonates was attempted giving rise to an unusual bicyclic oxetane product, which may be upcycled through appropriate copolymerization methods.