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Built heritage constitutes an invaluable asset to be treasured and wisely managed in order to avoid loss of place identity, cultural and social degradation and loss of leisure and tourism opportunities. The present paper focuses on the modern built heritage of the Thessaly Region (Greece), giving special emphasis to the “konakia” monuments built during the late 19th and early 20th century that were once used as residences by the big landowners of the Thessalian agricultural plain (“tsiflikia”). Field research conducted, as well as a survey of secondary data, revealed that only fifteen (15) “konakia” remain in Thessaly, equally dispersed in Larisa, Trikala and Karditsa Prefectures. Given their use, all of the “konakia” are found within—or in the vicinity of—agricultural land and settlements. Most of them present severe signs of abandonment, while only four (4) of them are in use (either as second-homes or as spaces with cultural and administrative use). Starting in 1979 (until 2005), with the exception of the Averof “konakia”, all of the rest have been designated as part of the modern built heritage of Greece. Considering these facts—and that most of such properties are private—the paper proposes a six (6) step methodology, for their wise management and integration in the spatial and cultural landscape of Thessaly: (1) Selection of the proper type of (re)use of the monument(s), (2) selection (or reconsideration) of the protection status and zoning, (3) identification of the urban regeneration interventions, (4) introduction of the necessary amendments to the urban/local plan, (5) selection of the proper financial tools and (6) selection of the proper marketing strategy. The paper concludes by highlighting the need to address the “konakia” as a set of monuments, to achieve stakeholders’ engagement and local community involvement, without undermining either protection status or the private rights of owners over these cultural properties.