The utilization of renewable sources as alternatives for petroleum and natural gas products has immense commercial, health and global warming significance. D-Isosorbide (2) is a bifunctional, polar, chiral and rigid molecule, which is produced from renewable sources. Synthesis of new polymers containing 2 is of interest for polymers and in drug delivery. The aim of the present work is to synthesize various polymers (homo- and copolymers) containing 2 via the olefin metathesis routes, ring-opening metathesis polymerization (ROMP) and acyclic-diene metathesis polymerization (ADMET). N-Phenyl-7-oxanorbornene-dicarboximide, and norbornene functionalized onto 2 were used as the monomers for ROMP. These monomers were polymerized using Grubbs’ catalysts to generate a series of homo-, co-, block and cross-linked-polymers. These polymers were characterized using GPC, NMR, and IR. In addition, ADMET polymerization of a terminal diolefinunctionalized D-isosorbide (2) was also conducted to produce ADMET polymers.