The synthesis of hyperbranched methacrylates was achieved by self-condensing group transfer polymerization of 2-(2-methyl-1-triethylsiloxy-1-propenyloxy)ethyl methacrylate (1). ''Back-biting'' is shown to be the predominant side reaction. In spite of this, the compact nature of the hyperbranched molecules was demonstrated through SEC-viscosity measurements and comparison with it linear analogue. The degree of branching can be controlled by copolymerization with conventional monomers, e.g. MMA, and the living polymers can be used as macroinitiators for star-shaped polymers.