Herein we report the first example of the controlled synthesis of linear and hyperbranched copolymers of 2-methylene-1,3-dioxepane (MDO) with functional vinyl monomers to deliver a range of functional, degradable polymers by reversible deactivation radical polymerization. The copolymerization was able to be tuned to vary the incorporation of degradable segments to create degradable materials with predictable molar mass, low dispersity values while also featuring side-chain functionality. The formation of nanoparticles by the addition of divinyladipate to form degradable hyperbranched copolymers was proven by DLS and TEM analyses.