Reversible addition–fragmentation chain transfer (RAFT)-mediated polymerization has been implemented in commercially available bulk-fill dental composites, with the idea of either optimizing polymerization at depth, while providing sufficient opacity, or reducing exposure time. The elastoplastic and viscoelastic behavior of the materials pursuing both ideas are described comparatively in connection with the microstructure of the materials and artificial aging. A 3-point bending test was followed by reliability and fractographical analyses. The elastoplastic and viscoelastic behavior was monitored with an instrumented indentation test equipped with a DMA-module at various frequencies (0.5–5 Hz). Data reveal that the similarity in filler loading is reflected in similar elastic moduli. Increased strength was offset by higher plasticity and creep and was related to microstructure. Aging showed a significantly stronger influence on material behavior than differences in composition. The elastoplastic parameters of both materials deteriorate as a result of aging, but to a material-specific extent. Aging has a strong influence on elastic material behavior, but very little on viscous material behavior. The parameter that is most sensitive to aging is damping behavior. Detailed laboratory characterization indicates comparable in vitro behavior with clinically successful materials.