We report a new strategy to synthesize densely functionalized highly and hyperbranched glycopolymers. Our methodology combines living radical polymerization and click chemistry. Hyper-branched "clickable" scaffolds synthesized via RAFT polymerization are functionalized with carbohydrate groups using an array of "click" chemistry reactions, namely Cu(I)-catalyzed Huisgen 1,3-cycloaddition of azides and alkynes (CuAAC), thiol-ene addition, and thiol-yne addition. This simple and flexible method yields glycopolymers of unique structures, which are potential candidates for biomedical applications.