Price: $920,000

I seriously doubt Walter L. Newberry had condos in mind when he bequeathed money to a school and a library on Dearborn Street nearly 150 years ago. The wealthy businessman died at sea in 1868, and his fortune, in addition to supporting his widow and daughters, was directed toward a location for a girls’ college prep school and a large circulation library. Reality came close to the mark: the landmark Newberry Library is a reference library, and the mansion at the southeast corner of Dearborn and Chestnut was built as the home of Miss Grant’s Seminary for Young Ladies, which for years prepared girls of means for women-only colleges.

In the 1980s the Newberry Mansion, as it’s now known, was converted to six condos. The largest of these, a 2,700-square-foot triplex, is new to market with an asking price of $920,000. Every unit has a personalized build-out and décor, and this one balances a whimsical and striking modern architectural retrofit with traditional finishes and furnishings. It may not make the most sense to buyers, but at least the part that stays with the sale is the part that can be adapted to contemporary tastes. The home has two very social floors with 12-foot ceilings connected by a gaping cutout and bizarre wood frame constructions that intervene in the open space. These abstract supports are complemented by tall church-like windows and a slender staircase to the lower living area.

On this lower floor (actually level with the street) you’ll find the primary living room with angular walls and a polished stone fireplace, a large designer kitchen, and a snug dining area in the corridor between the two. A private courtyard belonging to another unit teases through the kitchen windows, but not to worry—there is a common roof deck with very fine city views.

The middle floor is kind of the main floor even though it has less essential spaces. A second living area hangs above the primary one, and the sellers have a baby grand at the edge of the balcony. I asked if it could be part of the sale and listing agent Paul Gorney of KoenigRubloff didn’t say no. Behind the living area is a parlor space with a bar and bathroom that’s currently being used as office.

Finally, the upper bedroom level provides a sharp contrast to the hyperactive lower levels. Another long staircase shoots straight to the master bedroom. It and the two other bedrooms are large and plain, but again it’s a matter of décor. The space is here for you to play around with.

Price Points: Sellers Kathy and Gary Getz bought the unit three years ago and are relocating for work. They made minor upgrades and improvements but all the big-ticket stuff, including the custom build-out, has been in place for a decade or so. Their price paid in December 2011—$829,000—is $91,000 below the new asking price, but their ask is only $20,000 above what the previous sellers originally sought. In other words, it’s a conservative markup.

Another of the building’s units sold in June 2014 for $929,000. It’s a fair comp because it’s also a triplex, has very attractive modern interiors, but is 500 square feet smaller than today’s listing. “This is one of the most unique properties you’ll find,” says Gorney. “I think in this case it’s a positive; it can sometimes be negative.” He’s referring to the market for eccentric homes, which can easily turn against a seller. For proof look no further than Andrew Rebori’s nearby Fisher Studio Houses—sexy and awesome, but fairly impractical.