The decade's winners and losers in real estate

During the decade that just ended, the housing market in Chicago was slower to recover from the previous decade's boom and bust than those in most cities.

While the decade was mostly mild for the region overall, there are hot spots of remarkable growth, as well as ice-cold spots that saw especially deep declines as homebuyers' tastes and means made a pronounced shift.

Here's a look at some of the decade's gainers and losers.

GAINER: West Loop

At the start of the decade, the West Loop was grappling with an overhang of unsold condos from the 2007 housing bust, and with the impending departure of one of its longtime anchors, Oprah Winfrey's Harpo Studios, which was decamping for Los Angeles after 20 years operating out of an old armory on Washington Boulevard.

By the time the decade ended, it was the hottest neighborhood in town. That's both on the residential side, with 101 condos sold at $1 million including a record-setting $5.7 million sale, and on the commercial side, where developers, Crain's Alby Gallun wrote recently, "have been piling into the market," with numerous big buildings going up in the Fulton Market section of the West Loop.

GAINER: @properties

Over the course of the decade one major real estate brokerage grew out of proportion to the others.

Between 2010 and 2018, @properties' sales volume more than quadrupled, according to reports on the two years from Real Trends, a Colorado-based industry tracker. The firm reported a little more than $2 billion in volume in 2010 and 4.4 times that much, or $9.1 billion, in 2018. (Comparable data for 2019 is not yet available.)

That's more than double the growth in sales volume at two other major brokerages, Coldwell Banker (2018 volume was 1.5 times 2010) and Baird and Warner (1.9). Berkshire Hathaway HomeServices Chicago's 2018 sales volume was about 99 percent of the 2010 volume of its two predecessor firms, Koenig & Strey/Home Services and Prudential Rubloff.

The number of @properties agents grew from about 1,000 to more than 2,500 during the 2010s.

GAINER: South Side housing

The foreclosure crisis hit the city's South Side hard, and as the decade dawned, more than 1 in 20 properties were in foreclosure in neighborhoods including South Shore, Washington Park and West Pullman. That's compared to less than 1 in 30 citywide, according to data from the Institute for Housing Studies at De Paul University.

Two waves of upgrades have swept through the South Side in the decade since.

Rehabbers have fixed and flipped thousands of homes that were lost in foreclosure, making improvements and updates that the previous, cash-strapped owners couldn't have afforded. The result is a refresh of a large pool of affordably priced homes on the city's South Side.

In Bronzeville specifically, a building boom has been filling in long-vacant lots with new homes, which is fueling a stabilizing comeback for the historic neighborhood. In 2019 alone, 51 homes have sold for $500,000 or more, most of them new or newly rehabbed.

GAINER: The Milwaukee Avenue corridor

Reversing the flow of previous generations out of Milwaukee Avenue to the suburbs, a new generation of city-loving buyers and renters has helped revitalize every neighborhood that touches the avenue, from Fulton Market up to Edison Park. Bike lanes, breweries and boutiques have followed them in.

LOSER: Baby boomers' dream houses

Big suburban houses surrounded by a lot of lawn, the dream house of many a baby boomer, have turned into the real estate market's albatross, as the next generation of buyers turns its attention to smaller, more urban homes.

For a couple of years now, Crain's has been chronicling the homes, mostly in farther-out suburbs, that linger on the market and sell at sizable discounts from past sale prices.

It's likely to get worse. In November, the Wall Street Journal reported that over the next decade, aging baby boomers will sell one-quarter of the nation's single-family homes—or try to.

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.

LOSER: Prairie style

Sad as it is to say about a housing style that was born in Chicago, Prairie-style homes have lost buyers' attention in the past decade. In part, they've been swept out with all types of vintage homes by a homebuying public with a pronounced taste for new and modern.

Among the examples of hard-to-sell homes by Frank Lloyd Wright and his fellow Prairie-style architects:

A house in Glencoe that Wright designed for his attorney was on the market from July 2016 until selling in late December for $750,000, more than $1.1 million below the original asking price.

A piece of a Wright-designed estate in Riverside sold in February after more than eight years on the market. Its sale price appears to be less than the seller paid to buy and restore the home.

A home made out of a former women's club building designed by William Drummond in River Forest, which hit the market at just under $1.6 million in 2012, was marked down to $632,000 by October, when it went up for auction as a foreclosure. The results of that auction aren't yet in public records, but an attorney for the lender, Alliant Credit Union, told Crain's in December that a Cook County judge will consider a motion to approve a sale contract in early January.