Density values are essential for the characterization of wood elements in existing structures. A new method for the in-situ density estimation of timber pieces is proposed based on weighting the residue generated by conventional drilling. This research includes the design and development of a residue collector device coupled to a conventional drill and testing on four Spanish coniferous species: Laricio pine, Scots pine, Radiata pine and Maritime pine (Pinus nigra Arn., Pinus sylvestris L., Pinus radiata D. Don. and Pinus pinaster Ait., respectively). For each species, 44 specimens (except Scots pine, with 42) 60 × 90 mm cross-section and 150 mm length (half radial and half tangential orientation) were tested. Specimen density was obtained by mass/volume ratio. Three 8 mm diameter 46.5 mm deep holes were drilled in each specimen using a brad point bit. The drilling residue was weighed and density was calculated as a ratio to bore volume. Although only slightly smaller, residue density statistically differs from average specimen density. But the specimen density can be inferred by the correlation, statistically significant, with residuals drilling density (R2 = 80.7%) and even better with residual drilling mass (R2 = 84.4%).