As prices in metropolitan cities increase, it's likely you'll be shopping for real estate a bit farther out from the city center, O'Leary says.
"Most of the time you're going to be looking in the suburbs because nobody can afford to live downtown," he explains.
Indeed, the cost to live in major cities versus right outside can be striking. In the U.S., homes in urban zip codes have a median value of $315,988, while homes in the suburbs have a median value of $234,443, according to real estate site Zillow.
Here's how that looks in a place like Denver: The median per-square-foot cost for a home with an urban zip code is $332.12, while the median per-square foot cost for a home with a suburban zip code is $236.63, Zillow's data show. That means for a 1,000 square foot house, you're looking at paying $332,120 in the city versus $236,630 a bit farther out.
But when buying in the suburbs, it is crucial to pay attention to what amenities are nearby, says O'Leary.
Ask yourself, "Is it close to good schools?" he advises. "Is it close to a bus or some kind of transit line or subway? That is also very useful. Is it close to a grocery and drug store?
"People that live in homes want to be close to the services they need."
However, don't stray too far outside of a city or popular area. "Being just outside of town is not so bad," he says, "but if it is a 20-minute drive into the country, that is going to be tougher to sell because fewer people are going to want that."
As a bonus tip: O'Leary suggests thinking of garages as a nice addition, but not a necessity.
"Frankly the way people are looking at cars in the future, they're going to Uber everywhere, they're probably not going to own one." O'Leary says. "Think about that, that's less important down the road."