Conducted within the framework of Mykolaiv’s post-war reconstruction masterplan, this study offers a critical assessment of the city’s architectural heritage under the constraints of remote research and limited access to primary sources. It examines the narrow scope of Mykolaiv’s official Cultural Heritage List, which strongly emphasizes 18th- and 19th-century monumental architecture while underrepresenting the city’s diverse 20th-century built environment, particularly architecture from the Soviet era. The research identifies significant chronological and typological gaps, especially with socialist-period residential complexes, public institutions, and urban planning models. Drawing on comparative examples from other post-socialist and Ukrainian cities, the article calls for a more inclusive and comprehensive approach to heritage recognition. Based on a shortlist provided by the municipal authorities, the study analyzes a series of sites. It selects two pilot projects—the Shukhov Tower and the House of Naval Officers—as key case studies. These examples demonstrate how architectural heritage can work as a strategic tool for post-conflict urban regeneration. The article concludes by advocating for legislative reform, institutional engagement, and expanded scholarly inquiry to ensure that Mykolaiv’s layered and contested 20th-century heritage is properly acknowledged, protected, and incorporated into future urban development strategies.