In this work, a new family of polyhedral oligomeric silsesquioxanes (POSS) based esters have been synthesized that consists eight ester functional groups. These are classified into Type-I and Type-II esters based on the starting materials, octakis(3-chloropropyl)silsesquioxane (Cl-POSS) and octakis(3-hydroxypropyldimethylsiloxy) octasilsesquioxane (OHPS) respectively. These new POSS type ester moieties can be used as insulating oils and oil additives in the transformers and also considered to be alternatives to mineral and vegetable oils that are presently used in the insulation system.