Planar assemblies of plasmonic nanoparticles have provided opportunities in various fields. This study exploits the self-assembly of gold nanorods (AuNRs) into planar, layered chiral superstructures (dodecamer) using DNA origami technology. Due to the collective plasmonic coupling modes, the dodecamers exhibit g-factors of up to +0.06, which is 4–5 times higher than those of the dextrodimers. The chiroptical property of the superstructures proved to be strongly size-dependent, exhibiting enhanced g-factors with increasing the size of AuNRs. Moreover, by excluding the averaging and close-to-racemic effects in the ensemble colloids, circular differential scattering (CDS) and circularly polarized luminescence (CPL) were studied at the single-particle level, revealing the essential role of the structural chirality of superstructure in correlating single-particle scattering with nearby dye emission. The observed correlated CDS and CPL show g-factors up to −0.17 and −0.6, respectively. These results highlight the potential of DNA origami-directed plasmonic assemblies for nanoscale chirality engineering, with applications in biosensing, chiral photonics, and metamaterials.