Bioprinting of smart skin structures is emerging as a versatile platform not only for wound coverage but also for potential sensory regeneration, real-time monitoring of structures, and tissue repair. This review presents a comprehensive roadmap to bridge the gap between biofabrication science and clinical translation. We explore investigations related to piezoelectric scaffolds, conductive polymers, and stimuli-responsive inks in preclinical environments to produce functional features such as thermal and tactile sensing. Early clinical case reports have demonstrated the feasibility of in vitro skin bioprinting strategies, such as skin patches printed for patient-specific applications using minimally manipulated autologous extracellular matrix and umbilical cord mesenchymal stem cell-laden hydrogels for the management of chronic wounds. In parallel, several preclinical in situ bioprinting studies using handheld or microfluidic-assisted devices have shown promising results in full-thickness diabetic and burn wound models in terms of enhanced re-epithelization and neovascularization. We also present inherent differences between in vitro bioprinting of autologous dermo-epithelial substitutions and in situ strategies based on artificial intelligence-guided print path generation and wound topography mapping. Although sensor-equipped bioprinted grafts have shown promising results, they are still in the early stages of development and require validation in large-scale clinical trials. Nevertheless, integration of stem cell technologies, smart biomaterials, and bio-intelligent control systems may eventually be used to support bioprinted skin constructs not only as replacement tissue, but also as potential living, sensing interfaces. This broad multidisciplinary convergence may be beneficial in redefining skin repair by enabling dynamic interactions between engineered skin grafts and host tissue physiology.