We propose a chiral valence-bond solid (VBS) in which spin-singlet bond order itself spontaneously acquires handedness without magnetic order. Using a spin-lattice model on the diamond lattice, we demonstrate two enantiomorphic VBS states. In the presence of anisotropic spin interactions, this emergent handedness is inherited by chiral triplons with spin-split bands and spin textures that reverse between the two enantiomers. These textures generate a temperature-gradient-induced net spin response whose sign is set by the VBS handedness. The imaginary off-diagonal components of the dynamical spin structure factor encode the triplon polarization and change sign between the two enantiomers, enabling direct detection of chiral triplons and the selected handedness by polarized inelastic neutron scattering. Our results establish a direct connection between spontaneous chirality and magnetic excitations, opening avenues for exploring the interplay between quantum magnetism and chiral physics.