In this study, we have synthesized a series of poly(ester ester) based thermoplastic elastomers (TPEEs). Hard segment (HS) was prepared via transesterification of 1,4-butanediol (1,4-BDO) and Dimethyl terephthalate (DMT). On the other hand, soft segment (SS) was prepared via poly(ε-caprolactone) (PCL) diol by using ε-Caprolactone (CL), Etheylene glycol (EG) as initiator and DMC catalyst. The effect of the cyclic ester on the properties of the elastomers was investigated by modifying molecular weight of poly(ε-caprolactone) (PCL) and the HS/SS ratio. The resultant TPEEs were characterized by nuclear magnetic resonance spectroscopy and gel permeation chromatography. Their physical properties were investigated using universal testing machine, Thermogravimetric analysis, differential scanning calorimetry and dynamic mechanical analysis.