In cross-laminated timber (CLT) buildings, in order to reduce the disturbing transmission of sound over the flanking parts, special insulation layers are used between the CLT walls and slabs, together with insulated angle-bracket connections. However, the influence of such CLT connections and insulation layers on the seismic resistance of CLT structures has not yet been studied. In this paper, experimental investigation on CLT panels installed on insulation bedding and fastened to the CLT floor using an innovative, insulated, steel angle bracket, are presented. The novelty of the investigated angle-bracket connection is, in addition to the sound insulation, its resistance to both shear as well as uplift forces as it is intended to be used instead of traditional angle brackets and hold-down connections to simplify the construction. Therefore, monotonic and cyclic tests on the CLT wall-to-floor connections were performed in shear and tensile/compressive load direction. Specimens with and without insulation under the angle bracket and between the CLT panels were studied and compared. Tests of insulated specimens have proved that the insulation has a marginal influence on the load-bearing capacity; however, it significantly influences the stiffness characteristics. In general, the experiments have shown that the connection could also be used for seismic resistant CLT structures, although some minor improvements should be made.