Preserving the built heritage, maintaining the original exteriors of historic apartment buildings, and achieving today’s living standards and ambitious environmental objectives require a multidisciplinary approach encompassing cultural, economic, legal, social, environmental and historical factors. This study aims to assess the need for renovation and the cultural and environmental value of historic apartment buildings. Architects, conservators and civil engineers have been involved to evaluate the authenticity of materials and forms, their technical condition and suitability to the historic urban milieu across 19 building components. Our findings reveal significant replacement activities in various elements such as roof coverings, roof eaves, façades, stairwell windows, stairwells, exterior doors, and window and frame distribution, with a particular focus on materials rather than geometry. Notably, there is often a lack of original materials of the windows. When comparing materials and geometries, we observed a higher frequency of material replacement. While the immediate need for intervention may not be urgent, many historic apartment buildings are at risk of imminent material deterioration, necessitating timely renovation. The deep renovation approach, which extends the service life, enhances energy efficiency and indoor climate and restores the exterior aesthetics, offers a threefold benefit. However, aligning the current reconstruction requirements with the preservation of milieu values may remain ambiguous, leading homeowners to resist or overlook these obligations. Consequently, a culture of step-by-step (staged) renovation emerges, contributing to an eclectic appearance of the historically valuable area and promoting the use of inappropriate materials. In conclusion, this research emphasizes the importance of a holistic approach to building renovation, which yields architecturally superior and technically sustainable outcomes. The current study underscores the necessity for a shift in the authorized heritage discourse in Estonia. Rather than primarily imposing restrictive measures on construction and renovation projects, the focus should pivot towards effective communication of historical values. It is crucial to provide support and guidance (not restrictions) to building owners, designers and builders in this regard.