This essay traces a personal and generational journey of middle-class housing in India, set against the backdrop of urban peripheral expansion. Through the lens of one family's pursuit of homeownership on Bangalore’s outskirts, it examines how emotional aspirations, financial pressures, and speculative real estate logics intersect to shape the built environment. The story reveals how decisions driven by dreams of security and belonging become entangled in broader urban processes, such as land speculation, infrastructural development, and shifting housing markets, ultimately transforming homes from intimate refuges into investment assets. The essay situates this experience within broader debates on urban sprawl, peripheral urbanisation, and the evolving meaning of domestic space in contemporary India.