The rising tide of Chicago’s real-estate recovery—the price of the median single-family home in the metro area has risen 16 percent since August 2012, to $197,500, according to the Illinois Association of Realtors—has lifted some boats more than others.

In the past year, a Michigan Avenue condo sold for $15 million, and a couple of Winnetka mansions went for more than $12 million each—two of only three houses in the leafy village ever to surpass that mark.

“When the market was worse, a lot of [sellers] held back,” says Linda Levin, a vice president of Jameson Sotheby’s International Realty. “[Now] there’s more of a sense of confidence.”

Hence a recent wave of pricey listings, including the houses below.

LAKE BLUFF (above)

$9.9 million Boasts 7,000 square feet on three acres, plus a tram down the bluff to a private beach.


A high-end home in Hinsdale

Photo: @Properties


$9.5 million Includes an outdoor pool, wine cellar, and shared ownership of a private lake.


A high-end home in Gold Coast

Photo: Ratko Radojcic


$9.95 million Features 14 bedrooms, 10 full baths, and craftsmanship that dates back to 1896. Here's a bit more about this one.


A high-end home in Highland Park

Photo: Larry Malvin


$17.5 million Sits on a 25-acre farm that has horses and llamas in its 20-stall stables.