This article presents the seismic assessment and retrofit design of an existing old building in Greece of great regional importance. The Building is the “Administration building of Kalamata” located in the city of Kalamata, capital of the Messinia Prefecture. The Building, the largest in the city, is a seven-floor reinforced concrete (r/c) structure with a basement built in 1974. The seismic assessment procedure is based on the provisions of the EN 1998-3 code and the Greek code for structural interventions “KAN.EPE.,” introducing several novelties that give solutions to difficult practical problems with respect to the modeling, the analysis methods, and performance evaluation framework. The article presents details of the Building’s modeling, description of the analyses, and the corresponding results, as well as the most efficient retrofitting schemes that fulfill the safety demands (i.e. performance level B or “Life safety” and performance level C or “Collapse prevention” according to KAN.EPE.), considering cost and minimal disturbance both for the superstructure and foundation interventions. While considering the various intervention solutions, it proceeds with new simplified ways that optimize the proposed solution. As such, it can be used as a paradigm for finding clever, practical, and at the same time economical solutions. An interesting characteristic of the Building is that it has been strengthened already after the damaging earthquake of 1986, but the new usage requirements raised questions about the adequacy of that earlier strengthening. Last, but not least, it must be mentioned that this building is unique in the sense that the main earthquake record (a strong motion accelerogram) obtained during the damaging 1986 Kalamata earthquake was at its basement. This record is also used for the assessment.