While a growing number of researchers have provided series of tough critiques of the typology-led heritage value assessment over the recent years, the impacts have been constrained by the continued obsession with expanding the list of the predetermined value typologies rather than escaping its limitations. While these sustained debates have provided important insights, this article argues that operationalizing these predetermined ‘one-size-fits-all’ value typologies is symptomatic of a number of shortcomings, especially in the context of capturing the pluralities of values in contextualized heritage such as vernacular architecture. It also often undermines inclusivity and participation in the valuing processes. However, rather than simply rejecting the values-based paradigm, this article proposes a conceptual value assessment framework that is informed by the theorization of vernacular architecture as a contextualized heritage. The proposed Vernacular Value Model (VVM) puts forward the ‘when(s)’ and ‘how(s)’ of amalgamating both technical and normative processes to capture the range of contextual values present in built vernacular heritage. To this end, this article posits that by drawing on such a proposed flexible framework, the conservation strategy for built vernacular heritage can be propagated as an inclusive and participatory process which captures the wide range of values for a more sustainable practices for conservation.