Conductive polymers are an ideal material for application in health monitoring biosensors in wearable electronics because of their electrical conductivity, large surface area, and environmental stability, and for that purpose it is necessary for them to be stretchable and self-healable. This can be achieved by introducing side chains containing hydrogen bonding species which enable non-covalent cross-linking between conducting polymers, while maintaining the high conductivity of the backbone. In this work, a novel multiphase design for highly stretchable, room temperature healable and conductive polymers is used. The backbone consists of poly(3,4-ethylenedioxythiophene) (PEDOT) onto which polycaprolactone (PCL) side chains are grafted. Anionic ring-opening polymerization is used as a tool for tailoring the desired graft polymers, which allows the assembly of polymers with specific tailored functionalities, in this case with optimal density and side-chain length. Different polymerization conditions were used to obtain different PCL chain lengths and effect on properties was evaluated by multiple techniques. The structural properties of the synthesized materials were characterized using techniques such as nuclear magnetic resonance (NMR), infrared spectroscopy (FTIR) and UV/Vis. The electrochemical properties were studied by cyclic voltammetry and four-point probe method, while the thermal properties were studied by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The analyses confirmed the successful synthesis of conductive graft polymers with increased stretchability while maintaining good conductive properties.