The Zestimate history for a condo I used to own is hilarious. There have been several sales of this property over 5 years, all at about the same price.
If you follow the Zestimate through time, it climbs rapidly until there is a sale, then it goes "oh shit" and plummets down to the sale price, which is barely different from the last time it was sold. This cycle repeats each time the property is sold.
Zillow is absolutely certain that this property should be rapidly increasing in value, no matter how many times it sells at about the same price it sold for last time.
When we sold the property, the agent told us it was in an awkward spot: too expensive for single people, not quite big enough for high-earning families. So it's stuck in price limbo as all the neighboring condos skyrocket.
Based on this experience, I remain convinced that there are micro-structural factors the fancy data science pricing models just can't seem to capture yet.