For a closer look at the house, launch the photo gallery.

List Price: $9.95 million
The Property: The facades of many historical Gold Coast houses tell you right away that there’s magnificence inside. This one does something different. It’s camouflaged—covered with ivy so that you can’t even guess what you’re going to find inside.

Entering the home, the first space you encounter is a grand arrival parlor with a wood-paneled staircase that soars up three stories past columns and built-in benches. When built in 1896, it was the arrival point for the entire 10,000-square-foot house, home of Frederick S. Winston, an early member of the law firm that came to be known as Winston & Strawn. Over the years, the house and coach house were divided up into ten apartments; more recently that’s been taken back to six. The main residence, where the people who own the entire property live, is adjacent to the parlor and has much of its historical detail in place.

In the original music room is one detail that was never messed with: a tile mosaic on the fireplace (one of ten fireplaces in the building). Sandy Shelton, the home’s seller, says that when her now-deceased husband, John, first bought the house in the late 1970s, several other historical bits were hidden.

“In the living room, the beams on the ceiling had been painted over [and] there was a drop ceiling in there,” Shelton says. Flanking the fireplace are two round windows with leaded glass “that had also been covered over with drywall. [John] noticed them from the outside and came in and took the drywall down.”

With some historical details restored and a lot of space, “it’s a happy house,” she says. “With the vines [covering front and back], it’s like somebody has their arms around you. The house is a great place to entertain. We danced.” (And in the video, you’ll note, she does just that, with her tiny dog.)

When the house was first built, more of the dancing would have been done in the ballroom, which is behind the main living floor in what’s now called the coach house. It’s a separate rental now, but standing in the dining room of the main residence, I could imagine the sense of procession that guests would have had, as they came up from the sidewalk into the arrival parlor, and then through the living room and the large dining room.

That grand scale of living meant that the mansion’s kitchen was really meant only to be used by the servants. It’s not a whole lot bigger now and hasn’t been updated in a few decades, so a buyer will probably combine it with the room next door, now used as an office, into a larger and more informal space like what we’d expect today.

As it’s laid out now, the main home has just two bedrooms, a large master and another (as well as two baths) on the home’s second floor. But there is much more living space outside the bedrooms, in the form of a four-level deck.

At the moment, the other half of the floor is now a separate apartment, but there’s an easy solution for that. The master closet leads out to a hallway near a formal entrance to the other apartment. Take down a wall, and the space in that apartment can be joined to the main residence. Other options include retaking the the third floor, which is now an apartment accessed by the main staircase, or re-incorporating the coach house and ballroom into the main residence.

Price Points: A buyer who doesn’t re-claim any of the apartment space would have a steady stream of income from the rentals. They now bring in $10,700 a month, but Shelton’s listing agent, Karen Kass, believes they’re undervalued and could bring in more.

This house is one in a group of high-end listings I wrote about in the November issue of the magazine, which is out this week. Last week, I posted a tour of a suburban member of that group.

Listing Agent: Karen Kass of Prudential Rubloff, 312-968-9682,