
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 308.366 or higher, 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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Even the most bullish research firm in this forecast roundup (https://fortune.com/2023/05/10/housing-market-home-price-predictions/) only thinks the housing market will be able to rise by 4.6% from March 2023 to March 2024. The index is currently at 293, so a 4.6% rise in prices (even if it occurred entirely in the rest of 2023, rather than taking until March 2024) would only hit 306 on the index, not even quite reaching your 308 threshold. And that is the most bullish of nine different firms, most of which think the housing market will stay flat or crash! So, I am thinking that a new all-time high is very unlikely this year.