Housing scholars stress the importance of the information environment in shaping housing search behavior and outcomes. Rental listings have increasingly moved online over the past two decades and, in turn, online platforms like Craigslist are now central to the search process. Do these technology platforms serve as information equalizers or do they reflect traditional information inequalities that correlate with neighborhood sociodemographics? We synthesize and extend analyses of millions of US Craigslist rental listings and find they supply significantly different volumes, quality, and types of information in different communities. Technology platforms have the potential to broaden, diversify, and equalize housing search information, but they rely on landlord behavior and, in turn, likely will not reach this potential without a significant redesign or policy intervention. Smart cities advocates hoping to build better cities through technology must critically interrogate technology platforms and big data for systematic biases.