Will 2008/2009 lows in real estate ever be broken? Adjusted for inflation, it certainly could happen again. Right now real estate is booming because the Fed is pumping a lot of money into the economy which is propping up the stock market and keeping interest rates at record low. However, if the Republicans lose the House, Senate and White House in the November election, they will do exactly what they did under Obama - vote against any discretionary spending increases and complain that it will increase the deficit. That could kill any recovery and trigger a major recession.
It will most likely happen in big cities like NYC or SF. They'll hit the 2009 lows for sure as people run for the hills. The rest of the country...unlikely. Unless of course there is a war on American soil. Then all bets are off.
In the Seattle area even regular plain vanilla houses are being bid up 10's of thousands of dollars during the pandemic. Might have slowed a tiny bit here and there in the region, but not really. I know someone that just sold their 70's non-descript average middle class house 2 months ago due to divorce bid up over a million dollars. We bought are little farm house in 1999 and paid it off a couple of years ago; it's up 50,000 from February of this year on Zillow and ReFin (FWIW). Just too much demand here.