This paper describes the synthesis and thermal properties in solution and bulk of poly(2-alkyl-oxazoline)s (PAOx) containing a methyl ester side chain. Homopolymers of 2-methoxycarbonylethyl-2-oxazoline (MestOx) and 2-methoxycarbonylpropyl-2-oxazoline (C3MestOx), as well as copolymers with 2-ethyl-2-oxazoline (EtOx) and 2-n-propyl-2-oxazoline (nPropOx), with systematic variations in composition were prepared. The investigation of the solution properties of these polymers revealed that the cloud point temperatures (TCPs) could be tuned in between 24 °C and 108 °C by variation of the PAOx composition. To the best of our knowledge, the TCPs of PMestOx and PC3MestOx are reported for the first time and they closely resemble the TCPs of PEtOx and PnPropOx, respectively, indicating similar hydrophilicity of the methyl ester and alkyl side chains. Furthermore, the thermal transitions and thermal stability of these polymers were investigated by DSC and TGA measurements, respectively, revealing amorphous polymers with glass transition temperatures between -1 °C and 54 °C that are thermally stable up to >300 °C.