The reactions of diglycerol-based 4-armed enantiomeric lactide oligomers (DG4LLAO and DG4DLAO, DGDLAO/DGLLAO = 1/1) and a 1,3-propanediol-based 2-armed rac-lactide oligomer (PD2racLAO) with hexamethylene diisocyanate produced bio-based polyesterurethane networks (PEU-DG4scLAO/PD2racLAOs) with different feed ratios of stereocomplex (sc) lactide oligomer (DG4scLAO = DG4DLAO + DG4LLAO) and PD2racLAO. Crystallization behavior and physical properties of PEU-DG4scLAO/PD2racLAOs were compared with those of the corresponding pentaerythritol- and glycerol-based polyesterurethane networks (PEU-PE4scLAO and PEU-GC4scLAO) with no PD2racLAO fraction. The X-ray diffraction analysis revealed that sc crystallites were formed without any homo-crystallization for PEU-DG4scLAO/PD2racLAOs 100/0-25/75 in a similar manner to PEU-PE4scLAO or PEU-GC3scLAO. Differential scanning calorimetric analysis for PEU-DG4scLAO/PD2racLAOs 100/0-25/75 revealed that the sc crystallites were not regenerated during a cold crystallization process of the quenched samples, but regenerated by isothermal crystallization from the melt. This result was a marked contrast to the previous result that sc crystallites were almost completely regenerated by the cold crystallization for PEU-PE4scLAO and PEU-GC3scLAO. Polarized optical microscopic analysis revealed that the incorporation of 25% of PD2racLAO enhanced the sc-nucleation efficiency, and further addition caused the reduction of overall crystallization. PEU-DG4scLAO/PD2racLAO 100/0 exhibited a higher elongation at break and tensile toughness than PEU-PE4scLAO and PEU-GC3scLAO. Tensile strength and elongation at break for PEU-DG4scLAO/PD2racLAOs decreased with increasing feed of PD2racLAO.