A multi-analytical approach has been employed to investigate the painting Natura Morta (1954–1955) by Andreina Rosa (1924–2019) to assess the state of conservation and to understand more about the painting materials and techniques of this artwork, which was recently donated by the painter’s heirs to the International Gallery of Modern Art Ca’ Pesaro (Venice-Italy). A comprehensive and systematic diagnostic campaign was carried out, mainly adopting non-invasive imaging and spectroscopic methods, such as technical photography, optical microscopy, Hyperspectral Imaging Spectroscopy (HIS), fiber optics reflectance spectroscopy (FORS), External Reflectance Fourier Transform Infrared (ER-FTIR), and Raman spectroscopies. Microsamples, collected from the edges of the canvas in areas partially detached, were studied by Attenuated Total Reflection Fourier Transform Infrared (ATR-FTIR) spectroscopy and Gas Chromatography-Mass Spectrometry (GC-MS). By crossing the information gained, it was possible to make inferences about the composition of the groundings and the painted layers, the state of conservation of the artwork, and the presence of degradation phenomena. Hence, the present study may be of interest for conservation purposes as well as for enhancing the artistic activity of Andreina Rosa. The final aim was to provide useful information for the Gallery which recently included this painting in its permanent collection.