The Transfer of Property Act, 1882 remains the primary statute governing transfers of immovable property in India. However, its colonial origins create definitional ambiguities and rigid doctrines that are increasingly incompatible with modern economic and technological developments. Designed for an agrarian context, it inadequately addresses contemporary forms of property such as intangible assets, complex proprietary interests, and digital transactions. This research adopts a doctrinal approach, analysing statutory provisions, judicial precedents, and scholarly writings to identify structural gaps. It focuses on three key issues: the absence of a clear statutory definition of “property,” the rigidity of future interests under section 13, and limitations in provisions on alienability and ostensible ownership. Judicial decisions such as Shantabai v State of Bombay, Duncans Industries Ltd v State of UP, and Girjesh Dutt v Data Din, illustrate how courts rely on interpretative tools like the degree and object of annexation test to address legislative gaps. The study finds that such judicial reliance leads to inconsistency and reduced transactional certainty. It also highlights inadequate protection for dependent claimants under section 39, particularly regarding maintenance rights under the Hindu Adoptions and Maintenance Act, 1956, where transfers may defeat legitimate claims. Further, section 54’s requirement of registered instruments limits recognition of digital and blockchain-based transactions. The paper concludes that the Act requires reform through clearer definitions, flexibility in section 13, recognition of digital transfers, and stronger safeguards like section 39 to ensure relevance in contemporary legal and economic contexts.