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Electrospun (e-spun) fibers are generally regarded as powerful tools for cell growth in tissue regeneration applications, and the possibility of imparting functional properties to these materials represents an increasingly pursued goal. We report herein the preparation of hybrid materials in which an e-spun d,l-polylactic acid matrix, to which chitosan or crystalline nanocellulose was added to improve hydrophilicity, was loaded with different amounts of silver(0) nanoparticles (AgNP) generated onto chestnut shell lignin (CSL) (AgNP@CSL). A solvent-free mechanochemical method was used for efficient (85% of the theoretical value by XRD analysis) Ag(0) production from the reduction of AgNO3 by lignin. For comparison, e-spun fibers containing CSL alone were also prepared. SEM and TEM analyses confirmed the presence of AgNP@CSL (average size 30 nm) on the fibers. Different chemical assays indicated that the AgNP@CSL containing fibers exhibited marked antioxidant properties (EC50 1.6 ± 0.1 mg/mL, DPPH assay), although they were halved with respect to those of the CSL containing fibers, as expected because of the efficient silver ion reduction. All the fibers showed high cytocompatibility toward human mesenchymal stem cells (hMSCs) representative of the self-healing process, and their antibacterial properties were tested against the pathogens Escherichia coli (E. coli), Staphylococcus epidermidis, and Pseudomonas aeruginosa. Finally, competitive surface colonization as simulated by cocultures of hMSC and E. coli showed that AgNP@CSL loaded fibers offered the cells a targeted protection from infection, thus well balancing cytocompatibility and antibacterial properties.