In this talk, I draw on theories of property, financial power, and the asset economy to analyze the intersection of big tech and big capital in the US housing market. During the COVID-19 pandemic, a market landscape already altered significantly by post-2008 depredations of financial actors wielding enhanced digital tools sustained new rounds of investor-fueled growth and record-breaking appreciation. I examine three interrelated examples of how the digital and the financial are jointly reconfiguring relations of inequality: the expansion of iBuyers; a major new wave of investment backing institutional-scale landlords in single-family rental, and; the growth of business models that offer a path to homeownership through renting or provide non-professional investors exposure to the home rental market. I also consider the implications of changing macroeconomic conditions for such market strategies and for inequalities of wealth and affordability.