Price: $425,000

“The little blue house on Schubert Avenue,” as locals know it, has been with one family since 1948. It had already been parceled into flats with the owner occupying the main level—a common thing in lean times. For the last few decades, two sisters have been at the helm as other family members have cycled in and out. A half-block from Clark and Diversey, this is prime Lincoln Park. Not surprisingly, there’s been little trouble renting out the ground floor three-bed apartment over the years. But with the decision to sell, that run is coming to an end.

The 1882 Victorian is picturesque and worn, particularly its insides. The apartment works for unfussy renters and boasts hardwood floors, a sensible layout, and high ceilings with a throwback glittery plaster popular in the 1950s. The ragged second level, accessible only by exterior stairs, makes a great low-rent or no-rent crash pad for grandchildren, nieces, and nephews—exactly its role for years. However, the home lacks a livable basement or attic or the potential for one. “The sellers [as sisters] grew up in the house and never thought about the basement or attic,” says listing agent Mirabel Selva of Coldwell Banker. “Today, we expect to live in them.”

One thing we can say for the low basement is that, according to the sellers, it has never taken water. The space sure does feel like 1882, with planked dirt floors and original old growth timber supports. Selva has started recommending a fill-in of the basement to interested parties, to rework the home on a slab foundation.

Preservationists will be happy to know that the home’s 25 x 52-foot alley-adjacent site makes a teardown a bad idea. With modern zoning restrictions, new construction could not resurrect the old house’s line-to-line footprint. Judging by the mega homes filling in portions of the block, your traditional luxury developer would take a pass. And so, Selva and her sellers are right to market the home to contractors and rehab developers willing to work within the existing envelope.

“We’ve had passionate interest from regular buyers with ideas to make a townhouse or guest house of the old frame,” says Selva. “When the scope of work becomes clear, they back out.”

The hassle isn’t for everyone. There’s a real chance to sink another $300,000 into the $425,000 property—but then you'd have a built-in garage, modern updates, and hopefully a much more special home than the nearby townhouses (which, by the way, go for about $725,000).

“It’s a no-brainer to buy the cheapest home in the most expensive neighborhood, if you have the time and drive,” says Selva. “If this was out East it would have sold a long time ago because people there are used to old spaces.”

Price Points: The sellers have shown their motivation. A few years ago, realtors gave inflated quotes—in the $600s. Basically, they figured the parcel alone warranted that price point. Then Selva posted the listing in June 2013 for $575,000 and the challenges to a sale became clear. By September, the price had cascaded down to $425,000, where it is expected to remain. It recently became the cheapest single-family in the area with the sale of this charming coach house in late July.