As measured by the Case-Shiller U.S. National Home Price Index, here: https://fred.stlouisfed.org/series/CSUSHPINSA
All time high for these purposes is the June '22 reading of 308.365. If at any time a 2023 reading returns at 277.528 or lower, this question resolves "Yes". Otherwise "No".
If no reading has resulted in a "Yes" resolution then the question will resolve "No" after the Dec '23 reading is reported around March '24. Betting will close EOY '23.
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277 would represent a -5% decline from today's index value of 293, which is a bigger drop than forecasted by all but one of the nine research firms in this forecast roundup (https://fortune.com/2023/05/10/housing-market-home-price-predictions/). So, as much as this Georgist/Yimby/soon-to-be-first-time-homebuyer would love it if your scenario came true, I am thinking that such a dramatic crash is rather unlikely this year, unless there is some kind of unexpected low-probability economic disaster (like a debt default or etc).