LOSER: Lake Forest estates
Throughout much of the 20th century, Lake Forest was the province of Chicago's wealthiest people. Meatpackers, bankers, Mr. T and others who made it big bought country homes or primary residences there.
In recent years, the Lake Forest estate market has been in the doldrums. Two former Sears CEOs, a Discover Card CEO and a retired ITW CEO, among many others, have all sold homes at big losses.
In 2008, three Lake Forest mansions sold for $4 million or more. In 2019: zero. Two Lake Forest estates, one on the lakefront on Mayflower Road and one nearby on Illinois Road, have spent nearly all of the decade on the market.
The problem? Estate homes are too old and too big, with commutes that are too long for today's tastes.