When Zillow launched 20 years ago, the home-buying process happened almost entirely offline. The company’s digital listings, combined with its innovative “Zestimate”—an estimate of a home’s value, based on the kind of data typically only available to real estate professionals—marked a turning point for the housing market. Zestimates weren’t exact representations of value, but they put power back in the hands of prospective buyers (to sellers’ and agents’ chagrin).........

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