When I was a kid, we almost moved to a house with an in-ground pool. Then we didn’t, and it’s been kind of like that ever since.
I even moved to Chicago, where there aren’t many. Zillow currently lists 789 houses with the keyword “pool” in the entire region, and lots of those are above-ground pools… which, you know, is fine. Check the “must have pool” box and you get fewer than 150.
And houses with in-ground pools tend to be pretty pricey in Chicagoland. On the other hand, that means they’re interesting, and perhaps none is more interesting than Scottie Pippen’s, which is on the market again, and would have been the coolest house on earth when I was a kid.
Yes, for $15 million you could have the GOAT’s Highland Park mansion, with its nine bedrooms, 19 bathrooms, full basketball court and gym, across more than 32,000 square feet. If your game is less showy, you might prefer the second-greatest Bull’s house. A perfectly respectable 8,228 square feet with seven beds and eight baths, gorgeous landscaping, tasteful wood shingles, and a centerpiece two-story living room with a bar. And like the homes of many hardworking Chicagoans before him, there’s a modest little basement bar. You’ll have to settle for a mere half-court gym, but it’s got the 33.
The reason this 7,000-square-foot mansion sprawls out so ranch-like is that it was built as a horse barn in 1910, so at least with this place the numerous Instagram-friendly sliding interior barn doors and exposed beams have some claim to authenticity. Rebuilt in 2007 and renovated in 2012, it looks back on its history with lots of hardwood, which continues into a gorgeous sauna. Right next to that is an indoor resistance pool with a sleek water feature that sends a shower of water down across the pool.
If you’re like me, you’ve probably missed the occasional hotel night this year. Sometimes it’s nice to have a martini at a bar and wander on up to bed. You can have that experience every night in this Gold Coast mansion, which… looks a lot like a hotel lobby, from the massive wet bar with a chairs-and-couches setup, to the marble floors, to the sunken conversation pit, to the huge wooden room divider, to the mezzanine office space that could even be the front desk if you really get into it. With five bedrooms, six bathrooms, and 10,000 square feet, it could just be a boutique hotel (check with your lawyer). The pool is just a lap pool, but you have to make some sacrifices to fit in a putting green.
Built in 1930 in a French manor style, this 11,494-square-foot house has all the amenities of an earlier era: a billiard (not pool, got it) room with a wet bar, tennis court, fountain, and a glass conservatory that connects the house to the driveway. The renovations have been appropriately genteel, with soft colors and richly patterned wallpaper—which makes the gilded dining room ceiling pop all the more. With 2.4 acres, there’s room to stretch out around the pool, or really lean into the already impressive landscaping.
It’s a lot cheaper, and much smaller than all the above—three beds, three baths, 2,091 square feet—but the gorgeous midcentury modern main room in this ranch house rivals any space in any of the mansions. The clever use of room dividers, like the two-story brick wall that holds a fireplace and separates the living room from the dining room, opens up the entire living area to the huge windows, skylights, and knotty hardwood ceiling. The result is a bit more of a cabin feel than your typical MCM ranch. Outside is a pool whose angles mirror the house, with a cute little MCM pool house.