Cross-laminated Timber (CLT) has become an emerging board material of wood construction that is strong enough to sustain a high-rise building. However, many wooden congregate housing units overseas that utilize CLT have poor sound environments because the low mass of such wood influences sound insulation performance. In this research, we explored the effect of different CLT walls on sound insulation performance and integrated applicable sound insulation simulation tools to simplify the process of designing a CLT wall structure. This research aimed at a double wall and CLT combined with a gypsum board as the research object. The sound insulation performance test was carried out in a laboratory, while the sound insulation performance of the structure was predicted through simulation tools and prediction models and then compared with the measured values to verify the applicability of the simulation tool. The CLT with a double wall and CLT with gypsum board (CLT + GB) achieved Rw of 50 dB. The numerical simulation had better prediction performance than INSUL at the double wall, while the double wall with cavity structure was close to the measured result via mass law calculation. The INSUL-predicted CLT with a gypsum board at 500 Hz~3150 Hz was close to the measured value.