The present study elucidates the facile synthesis and exceptional properties of a family of novel poly(ester amide)s (PEAs) based on bis(2-hydroxy ethylene) terephthalamide that was obtained from the poly(ethylene terephthalate) waste. Fourier transform infrared and 1H NMR were used to verify the presence of ester and amide in the polymer backbone. Differential scanning calorimetry data showed that the glass transition temperature decreased with as the chain length of dicarboxylic acids increased. Dynamic mechanical analysis and contact angle studies proved that the modulus values and hydrophobicity increased with as the chain lengths of dicarboxylic acids increased. In vitro hydrolytic degradation and dye release studies demonstrated that the degradation and release decreased with as the chain lengths of dicarboxylic acids increased. Modeling these data illustrated that degradation and release follow first-order degradation and zero-order release, respectively. The in vitro cytocompatibility studies confirmed the minimal toxicity characteristic of these polymers. Osteogenic studies proved that these polymers can be highly influential in diverting the cells toward osteogenic lineage. Alizarin red staining evinced the presence of twice the amount of calcium phosphate deposits by the cells on these polymers when compared to the control. The observed result was also corroborated by the increased expression of alkaline phosphatase. These findings were further validated by the markedly higher mRNA expressions for known osteogenic markers using real time polymerase chain reaction. Therefore, these polymers efficiently promoted osteogenesis. This study demonstrates that the physical properties, degradation, and release kinetics can be altered to meet the specific requirements in organ regeneration as well as facilitate simultaneous polymer resorption through control of the chain length of the monomers. The findings of this study have significant implications for designing cost-effective biodegradable polymers for tissue engineering. © 2017 American Chemical Society.