If you pledge to purchase at the Zestimate then people who reasonably think they can get more than the Zestimate on the open market don’t have an incentive to sell their house to Zillow (besides convenience). But people who think the Zestimate is an over estimate will of course sell to Zillow. So instead of a normal distribution of actual value:estimated value you end up with a skew towards the end where the estimate is over the actual value.
Trading housing is very different from normal market making because houses are not fungible commodities like most securities are. For most entities trading securities at low frequency it does not really matter whether a market maker skims off a few pennies on their trade; it’s worth it for the liquidity. Houses are less liquid (because they are non fungible) so the liquidity is more valuable, but the price improvement routing around a MM can also be many percentage points of a trade because there are not only so many factors affecting their valuation, but also just chance and random noise (bidding war, a particular buyer falling in love with the property, not-price-conscious buyers).