Following the decline of manufacturing at the end of the twentieth century, land and infrastructure speculation continued to drive suburban expansion at the edges of the city of Melbourne. Mass transit technologies allowed suburban sprawl in the 1870s through the construction of light and heavy rail, and again in the 1950s with the mass adoption of the private motor. These technologies significantly altered the urban landscape and shaped today’s city. Melbourne was laid out and developed in a way that projected where developments were going to be, such as along waterways, stock routes, rail corridors, and later, motorways. As the sprawl continues, it also appears ‘up’ is the new ‘out’. Increasing density in the inner city marks another phase in the reshaping of Melbourne. Speculation amongst the urban gentry surrounding the next suburbs to be gentrified accelerates the rate at which we see cranes claim the inner-city skyline; replacing warehouses with boutique cafes. Modest homes on long, narrow plots continue to be demolished, subdivided, and supplanted by modern townhouses. Is this at the expense of the low-density ‘Australian Dream’ and the cultural heritage associated with the urban frontier, or must we accept that taking to the skies is the way forward? Development occurred in four distinct phases of speculative development, dictated by changing technologies. Firstly, initial settlement along waterways in what would become the metropolitan area using traditional horse and cart modes of transport; the expansion of the walking-city with the installation of light and heavy rail; the explosion of suburban development with the mass adoption of the private motor; and finally the emergence of truly high-rise suburbs in the 21st century. Obsessed with all things speculative since its inception, this paper contends that Melbourne continues to do all it has ever known – remake itself.