Although bioinks with both high printability and shape fidelity while maintaining high cell viability are developed, the biofunctionality of the resulting bioprinted construct is often overlooked. To address this, a methacrylated gelatin (GelMA)-based bioink biofunctionalized with bone particles (BPs) is developed as a personalized treatment strategy for bone regeneration. The bioink consists of incorporating BPs of various sizes (0–500 µm) in GelMA at various concentrations (ranging from 5 to 15% w/v). The printability of the bioink is systematically investigated and it is demonstrated that a 15% w/v BP-loading results in high print quality for 10% and 12.5% GelMA concentrations. Rheological evaluation reveals a strong shear thinning behavior essential for printing and a high gel strength in bioink with 15% w/v 0–500 µm BPs for both GelMA concentrations. In addition, the printability of the bioink and the metabolic activity of the resulting scaffolds are dependent on both the concentration of hydrogel and size of the BPs. Importantly, the cells initially contained in the BPs are able to migrate and colonize the bioprinted scaffold while maintaining their capacity to express early osteogenic markers. This study demonstrates the feasibility of bioprinted viable BPs and may have some potential for chairside clinical translation.