Everyone in real estate says "buy in the off-season." I wanted to know if the data actually backs it up.

So I pulled 4,896 single-family sales across Highland Park, Mac-Groveland, Union Park and West 7th - six years, October 2020 through September 2026 - and measured what buyers actually paid relative to asking price, by the month they went under contract.

The gap between the best and worst month to be a buyer is $32,503. That's 7.4% of the median sale.

December: 68% of buyers paid under asking. 19% paid over.

April: 23% paid under. 67% paid over.

The discount size is nearly constant year-round - $20K to $27K. Seasonality doesn't change how much you save. It changes your odds of saving anything.

The mechanism is simple: a December contract lands on a listing that's been sitting 36 days. An April contract lands on one that's six days old.

Two things I'd flag before anyone runs with this:

1. It held in five of the last six years - 2021 through 2025, through a boom, a rate shock and a normal market. 2026 has run slightly the other way so far. Five for six is the honest claim, not six for six.

2. This is negotiating leverage, not appreciation. A 7.4% seasonal edge is smaller than the ~8% it costs to transact. You can't flip on seasonality alone. But if you were buying this year anyway, buying in Q4 instead of Q2 is real money for a decision you were already making.

One more finding worth its own post: the edge is largest above $650K (a $33,325 swing) and smallest in the $450-650K range where most families buy. Timing matters most for investors and luxury buyers, least for move-up buyers.

Happy to share the full month-by-month data with anyone who wants it.