(1) The assessment of the mechanical properties of old timber is essential for the proper maintenance of wooden structures. (2) Among the non-destructive properties, the dynamic modulus of elasticity is one of the best predictors of the mechanical characteristics of the members, but it requires the determination of wood density to be determined. (3) Thus, wood density was estimated by drilling resistance measurements, developing species-specific prediction equations for silver fir, chestnut and poplar. (4) The estimated density was combined with the stress wave velocity propagating longitudinally through the wooden piece, and the dynamic modulus of elasticity was calculated. (5) Medium-high coefficient determinations (R2 from 0.79 to 0.94) were found for density estimation, and medium coefficient determinations (R2 from 0.53 to 0.60) were found for the estimation of the static modulus of elasticity using the dynamic modulus.