The first polymerization exploiting the carbenic reactivity of homogeneous gold catalysis has been devised. In the presence of a gold catalyst, monomers incorporating both a propargylic ester and an alkene moiety polymerized through a metallocarbene generation/cyclopropanation sequence to afford the corresponding macromolecules. This approach constitutes an unprecedented example of cyclopropanation-based polymerization and allows access to original macro-molecule skeletons.