House RegretsThe house you didn’t buy.

The index-fund rebuttal

Waterbury-Shelton, CT, 1988: the year the spreadsheet people were right.

$60,000 as a down payment$767,976 equity$60,000 in an S&P 500 index fund$3.71MWinnerthe index fund

Take the same $60,000 in 1988. Route one: 20% down on a $300,000 Waterbury-Shelton, CT house, thirty-year loan at that year’s average rate. Route two: an S&P 500 index fund (the TSP C Fund), dividends reinvested, no tenants, no roof.

Route one is worth about $767,976 of equity today. Route two was worth about $3.71M at the end of August 2026, the latest month the fund has reported at tsp.gov. The leverage that makes house regret spectacular in Austin and San Francisco cuts the other way in the metros and years where prices went sideways: you paid interest for the privilege of standing still.

The calculator puts the same index-fund line beside every metro’s numbers for any purchase year from 1988 on, so you can test your own year against it.

Check 1988 Waterbury-Shelton, CT yourself

House figures are estimates for the whole metro market, from the FHFA index. Not financial advice.