We bought our dream house in late 2004. It was a seller's market, so we bought high, but not at the peak. We also sold the old house at a crazy-high price in early 2005. It sold twice post-2008 at significantly lower prices. Zillow has the current digs at a 26% premium to our 2004 purchase price, but that's about 90% of "cost," including major improvements that we made shortly after buying. So, we'll likely lose money when we sell, but we had no expectations to recover all that. At the depths of 2008-9, it never dropped much below our purchase price. Our area held up better than many parts of the country.
Zillow is reasonably accurate in our area. The houses are not cookie-cutter; they are large, late 60s unique designs, on 2-3 acre lots. A high percentage sell in a tight range around $90-100/ft2. Depending on condition, upgrades, lot size, etc, it might go a little higher or lower. When I look at Zillow values in our neighborhood, they're mostly in that range, and correspond closely to the county appraisal district's condition ratings.
In other parts of town, smaller investment-type houses are consistently selling for 10-20% above list and Zillow... all cash, and within a few days. Investors are squeezing out all the regular buyers in that market, which has been reported in the local news lately. Especially "fishy" is how certain investors manage to consistently bid a few hundred dollars higher than all the other bids. Our neighborhood generally takes several months to find a suitable buyer who wants a large, older house, on a large lot, with a pool, etc. But when they finally sell, it's very close to the Zillow estimate.