Anionic ring-opening polymerization and copolymerization of allyl glycidyl ether (AGE), tert-butyl glycidyl ether (tBuGE), and ethoxyethyl glycidyl ether (EEGE) was performed using potassium 3-phenyl-1-propanol as initiator. The polymers poly(AGE), poly(tBuGE), poly(EEGE) as well as poly(AGE-co-tBuGE), poly(AGE-co-EEGE), and poly(EEGE-co-tBuGE) were obtained with controlled degree of polymerization, narrow molecular weight distribution and a predetermined ratio of repeating units. First-order kinetics with respect to the glycidyl monomers were found for homo- and copolymerization. The removal of protection groups from the homopolymers was achieved using trifluoroacetic acid for poly(tBuGE), aqueous hydrochloric acid for poly(EEGE), and a palladium catalyst for poly(AGE); in all cases a linear poly(glycidyl ether) (poly(GE), 1) was obtained. The following conversions were achieved by selective removal of only one protection group: using aqueous hydrochloric acid, poly(AGE-co-EEGE) was converted to poly(AGE-co-GE) 4; using trifluoroacetic acid, poly(AGE-co-tBuGE) was converted to poly(AGE-co-glycidyl trifluoroacetate), 5; and by using Pd/C and p-toluenesulfonic acid poly(AGE-co-tBuGE) was converted to poly(GE-co-tBuGE), 3. A selective removal of only one protection group from poly(EEGE-co-tBuGE) was not possible. Treatment with aqueous hydrochloric acid or with trifluoroacetic acid lead to poly(GE), 1, and poly(glycidyl trifluoroacetate), 2, respectively. Finally free hydroxymethyl groups of the polymers poly(GE-co-tBuGE), 3, and poly(AGE-co-GE), 4, were partially converted in a polymer analogous reaction using propargyl bromide to the corresponding polymers with glycidyl propargyl ether (GPE) repeating units. In a model reaction one of these polymers with GPE repeating units was successfully converted with an azido sugar moiety in a (2 + 3) cycloaddition reaction.