Why Every 10-Year Window in Real Estate Creates Wealth — Even If You Buy at the “Worst” Time
In a recent meeting of The Diversified Investors Group Philadelphia (DIG Philly)- special guest, Gary Jonas of The How Group shared the following advice:
For decades, real estate investors have argued over timing the market. Should you wait for a dip? Buy during a crash? Sit on cash until conditions feel “safe”?
But data from every tracked market cycle points to one simple truth:
There has never been a 10-year period in modern housing history where a property wasn’t worth more than when you bought it.
Not one.
The Worst Time to Buy Still Wins After 10 Years
Take one of the most notorious examples:
Buying at the absolute peak in 2006–2007, right before the Great Recession.
If you held that property and sold around 2016, you didn’t just break even —
you were significantly ahead.
Even investors who "bought wrong" at the top of the cycle still captured meaningful appreciation once they held through a full decade.
The Best Time to Buy Also Wins
Now flip it.
Imagine you bought at the perfect moment — say 2014, near the bottom of that cycle.
Even if you sold in 2024, one of the toughest seller environments in recent years due to high rates and buyer fatigue, your property would still be worth far more than when you bought it.
Good timing?
Nice bonus.
But time in the market is the real engine of wealth.
The 10-Year Rule Investors Can’t Ignore
Across all cycles:
- Booms
- Busts
- Recessions
- Recoveries
- High-rate eras
- Low-rate eras
There has not been a single tracked 10-year period where real estate values didn’t rise.
That doesn’t mean every market behaves identically. Appreciation rates vary, demand changes, and demographics shift.
But the long-term trend never breaks.
What This Means for Today’s Market
The current environment is unusual:
- High interest rates
- Limited inventory
- Investors hesitant to deploy capital
- Many people burned on deals from 2020–2022
But that hesitation is creating the exact thing savvy investors look for: reduced competition.
And here’s the kicker:
If you believe real estate goes up every 10 years — and history says it does — and you can buy assets today for less than replacement cost, the smartest move is to buy as much as you reasonably can.
The Bottom Line
You can't control timing.
You can't predict the perfect entry point.
But you can control your hold period.
And if you hold for 10 years, the data is clear:
Real estate wins—every single time.
