Mass timber buildings have gained global popularity due to the increasing availability and affordability of mass timber products and an increasing awareness of the sustainability of timber construction. This paper presents an experimental and numerical study on coupled balloon-type cross-laminated timber (CLT) shear walls with the aim of overcoming the capacity limitations of platform CLT shear walls. Using self-tapping screws to create innovative hold-down solutions, three two-storey coupled CLT shear walls were cyclically tested and the results demonstrated that the proposed coupled wall systems could achieve significantly higher lateral strength (over 400 kN) and initial stiffness (up to 14 kN/mm) compared to platform CLT shear walls in literature. The cyclic test results were used to validate a finite element CLT shear wall model in CLTWALL2D. The calibrated model was then used to run a parametric study of a series of balloon-type CLT shear walls up to twelve storeys (42 m) in height. This study provided evidence that coupled balloon-type CLT shear walls with high-capacity screwed connections have the potential of reaching high strength and stiffness with the displacement ductility factor μ = 2–4.