Unreinforced masonry has been for centuries one of the most widespread constructive techniques for both massive structures and civil buildings (e.g., palaces, hospitals, houses), for the most still standing nowadays. Their future conservation relies on (i) their protection from main natural threats (e.g., earthquakes) and (ii) updating to current functionality and hygrothermal standards. In the former framework, existing masonry buildings proved to have some intrinsic vulnerabilities, depending on composition (units and binder) and structural typologies. Based on experience gathered from seismic events, various retrofitting techniques have been proposed. In such a context, the use of cross-laminated timber (CLT) components is a very promising solution, in terms of compatibility with built heritage and integration of seismic and hygrothermal performances. This paper aims at improving the knowledge of the structural performances of compound timber–masonry interventions by numerical simulations carried out at (i) pier scale and (ii) building full scale via finite element modeling and nonlinear static analyses (pushover). First, a coupled timber–masonry wall was simulated and underwent sensitivity analyses with the properties of both components varying; then, the optimized solution was applied to a case study to assess the intervention benefits, and the results were also cross-checked with those of more traditional interventions (e.g., grout injections).