We have developed recyclable chiral polymers from enantiomerically pure monomers through entropy-driven ring-opening metathesis polymerization (ED-ROMP). The 7-membered cyclic olefin monomers containing acetal functionality were prepared via a cascade reaction involving the hydroalkoxylation of alkoxyallene using a chiral Pd complex and ring-closing metathesis. Using the reversible reaction of the metathesis process, we could obtain the corresponding head-to-tail polymer at high concentration and low reaction temperature, thereby driving the equilibrium toward polymerization. On the other hand, depolymerization was demonstrated at low concentration and high reaction temperature in the presence of Grubbs catalyst. Additionally, acetals in the polymer backbone provided the degradability under various acidic media.