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List Price: $777,000
The Property: This house, in a part of Chicago called Wrightwood Neighbors, is a classic type of urban residence in its resemblance to a milk carton: tall and slender, with a peaked roof. And in this case, some of the contents are beyond their expiration date.

The exterior is appealing and the structure is sound, but the interior was last updated 20 years ago, with results that look ancient today. As you will see in today’s video, it’s the 1990s all over—which is why the home is priced as it is (see Price Points below). The seller, Freddi Friedman, and her listing agent, Michael Rosenblum, acknowledge that a buyer has a lot of updating to do.

One of the simplest tasks is to wipe out the blue sponge painting on the living room walls. That would return the visual emphasis to the room’s generous size and front bay of windows.

If the living room doesn’t shriek 1990s, then take a look at the baby aspirin–colored powder room—and then step into the kitchen and family room. Here you find a peninsula workspace set off at a jaunty angle that nobody would do today, as well as a fireplace whose explosion of tile mosaics is classic “zany” 1990s design.

Redesigning the space might also start at the conservatory that juts off the back of the family room. Its windows need replacing anyway, says Rosenblum, and the space is above foundation, so why not incorporate it into the main room? Renovations could include improving traffic flow by replacing the peninsula with an island and punching a hole through to the living room. But it’s possible to retain the kitchen’s ample cabinets, because they’re pretty cool—and keeping them would limit the scope of the work on this level.

That’s good, because the work would continue on the two upper levels, where a buyer can create up to four bedrooms. There are two now on the second floor—a front bedroom with its own bath and a balcony and, in the back, a large master suite. It has a big walk-through closet to a spacious master bath, where—hello, 1990s—the shower has a curved wall of glass block. Redoing that first-floor conservatory as a more conventional room would give it a flat roof; a master-bedroom balcony could be placed on top.

The third floor is now two large rooms and a bathroom. Re-allotting space here would depend on what happens to the basement. It’s now a rentable apartment, which means the main residence has no space for a playroom or TV room—these top-floor rooms serve those functions. But if that basement space were to be brought back into the main home, then one or both of the top-floor rooms might become bedrooms. Whatever happens up there would surely take advantage of the long strip of east-facing windows that bring in a lot of daylight.

Outside the top floor’s back room is a big balcony. Here’s where another 1990s design feature is showcased: the sculptural image created by a composition of windows and light fixtures. It’s nice to have this high-up balcony space, although the home also has a big deck as well as ground-level yard space and an alley garage (not to mention the front balcony). Those are all nice, but up here, the view takes in both the neighborhood, with new and old homes, as well as a stretch of downtown skyline that includes the Trump, Hancock, and Bloomingdale’s buildings.

Price Points: Rosenblum, the listing agent, has had inspectors and contractors in, and determined that renovating the interior may run about $150,000. That’s been factored into the asking price for this home, which stands in a neighborhood where comparably sized homes have recently sold for significantly more. This one went for $1.3 million in September, and this one got $1.875 million in November.

Listing Agent: Michael Rosenblum of Koenig & Strey; 312-893-8162 or