Price: $440,000

Though he gets far less attention, architect John S. Van Bergen did a fair job of pacing Frank Lloyd Wright in Oak Park with some two-dozen works. Contrary to his mentor, he relished in modest commissions. His Oak Park projects were mainly at the start of his career and often presented as pristine, pint-sized Prairies. The George R. Hemingway House is an excellent example. Ernest Hemingway’s uncle was a realtor and it appears his name stuck to this house only because it passed through his office. It’s more likely that Van Bergen may have self-commissioned the home on spec, as newspaper ads from the day seem to suggest.

The 1914 George R. Hemingway House is just 1,730 square feet with three bedrooms on the smaller side. A lot of that square footage makes up the living-dining-veranda combo. This is also where the fine woodwork, heavy and handsome windows, and roman brick concentrates. “In Oak Park, if anybody says they’re going to replace windows we talk them out of it,” quips listing agent Mary Carlin of Baird & Warner. None of it is overly ornate—that wouldn’t befit a spec home originally priced at $7,000. Rather, the brick hearth and oak trim are yesterday’s middle-class signifiers. The home has low ceilings, likely because Van Bergen was still closely aping Wright.

One spot where you don’t notice the tight headspace is the window-wrapped veranda. “The ceiling is barely seven feet, but we love being out there getting enveloped by the weather,” says owner Miriam Howe. She and husband Dean Stackler spent more time in this room than any other during their seven years. Originally a three-seasons space, they insulated the floors and refitted storm windows. Howe doesn’t feel they bought a fixer-upper, exactly, but there wasn’t one functioning appliance either. The house had been foreclosed and vacant for year. “It’s a good feeling to think we may have saved this important piece of Oak Park,” she says.

Someone had been mowing the front yard after the bank took ownership, but the backyard was a jungle. Howe and Stackler, who are retiring to coastal Carolina, did more yard work than interior work, and now the back boasts a patio and a highly productive garden. Fun fact: More than a century ago, the lot was stables for the towering Victorian next door. Today, as a result, it has the best soil Howe has ever encountered.

This property’s big anomaly is its four-car garage with running water and a chimney. Clearly, at one point some kind of workshop operated out of the garage. It can happen again, particularly were you to install a wood stove and punch out skylights in the pitched roof.

As for challenges, you have the low ceilings and limited space. There are two more: no central air conditioning and no second bathroom. Investment can fix both, but the fact that the lone bath is upstairs deters some buyers—particularly older people and families. You could take a portion of the front office for a second bathroom, but that sacks prized living space. “A lot of young families walk through and look to what has to be done to expand or alter the home,” says Howe. “A somewhat older set sees it a little differently.” A landmark district protects the integrity of the façade, but an owner is free to build an addition off the back.

Price Points: Listing in late March, the sellers had a contract for close to asking price by early June. It fell apart because the buyers, a couple in their 40s, had trouble selling their home first. “We normally don’t like to work with contracts that are contingent on buyers selling a property,” says Carlin, “but sometimes you just want someone who loves your home to buy it. They definitely loved it.”

The contract took the home off the market during prime selling season, because if you bring the listing right back online people tend to suspect problems with the inspection. It re-listed at the end of August, still just $15,000 above the foreclosed purchase price and $110,000 below what a previous owner paid in 2006.