The first and second generation neutral, water-soluble dendronized polymethacrylates PG1 and PG2, respectively, carrying hydroxyl groups in the periphery are reported. The threefold branched repeating unit of the dendrons are synthesized on the multigram scale using gallic acid as the branching point and tri(oxyethylene) (TEG) units as the linker. All dendrons and their corresponding macromonomers carry either free or THP-protected hydroxyl groups in the periphery. PG1 and PG2 were obtained by radical polymerization in bulk, in DMF, as well as in aqueous solution. The polymerization of the hydroxyl-terminated G1 monomer 3b proceeded at an exceptionally high rate in water. All polymers have high molar masses and are fully water-soluble. Their glass transition temperatures are in the range of -50 to -40 degrees C.