Despite being one of the world’s smallest countries by land area, Singapore ranks 6th globally in terms of land reclaimed. Increasing from 578 km2 to 719 km2 over two centuries, most of the land that houses top-performing global industries sit on reclaimed land - land that did not exist when the British first arrived on the island. Existing scholarship focuses on the research of land reclamation through a binary lens: either looking at early or contemporary Singapore. This research thus proposes to bridge this analytical gap by examining Singapore’s three distinct eras that form a complex interplay: from Singapore’s colonial founding to its early expansion during post-independence, and its contemporary transnational actions with regards to sand mining. Each era is examined through the lens of postcolonial theory – tracing material losses and impacts. The coastline becomes a physical and symbolic site of negotiation about authority and postcolonial identity. It prompts the question: How does Singapore use her own changing coastlines to legitimize authority and script its own historical and cultural identity? Through challenging the binaries of natural vs. constructed and colonized vs postcolonial, a new "freakosystem" - a term informally used by Ponsford (2025) to describe an accidental hybrid environment born of human intervention – begins to emerge from the Singapore landscape. Singapore’s sand story is a palimpsest that questions what it means to design this colonial-postcolonial-neocolonial "freakosystem" that does not overwrite the past but acknowledges and builds on it. In a truly postcolonial future, we stop asking whether our landscapes are pure but start asking how we might inhabit them more ethically and authentically.