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This Quirky Logan Square House Used to Connect to Bootlegging Tunnels

The 1901 four-bed has a walled-off piece of bootlegger tunnel that once connected to a Prohibition-era underground infrastructure. It’s on the market for $749,000.

An early Logan Boulevard home in the middle of new neighborhood excitement.   Photo: Ian Spula

Price: $749,000

An entry-level Logan Boulevard single-family has hit the market, with almost unbelievable positioning next to restaurants, cafes, and the hippest farmer’s market in the Midwest. With a DIY aesthetic to match the neighborhood of a decade ago, the restored brick four-bed is refreshingly imperfect amidst Logan Square’s contemporary infill and upscale renovations to old housing stock.

When Kimberly Oliva bought the house in 2002 for $380,000, the blocks radiating from the square hosted halfway houses and dive bars and not one smart brunch spot. “Basically, everything has changed around us,” Oliva says. “The bars on the windows are the result of someone trying to break in our first week here.” 

The home she purchased was worn and tired, but Oliva and a cast of roommates built around 114-year-old hardwoods and stained glass, bricked up voids in the wall, and turned a raw basement into a colorful rec room. “All the key maintenance that you have to be mindful of with a building this age has been taken care of in the last couple years,” says listing agent Dan Sullivan of Conlon Real Estate.

This early boulevard home has just 1,816 square feet of living space, but a trend toward smaller city dwellings and energy footprints (see Smart Tech Homes or the condo projects of Panoptic Group) could give an assist to this listing. The partially-finished basement doesn’t count towards this figure but certainly expands usable space with a billiards lounge and bar. The floor is tiled and the stone foundation painted white rather than squared off by drywall. Off to the side is a curious passageway to nowhere. This, according to Oliva, was the mouth of a tunnel leading to a network of Prohibition-era bootlegging tunnels beneath the boulevard used for transport and storage. It was navigable when Oliva first arrived. “We put on our hard hats and pushed through, but it was a better plan to seal it off to the rat population.”

The kitchen is more uniformly new and high-end than the rest of the house, because it kind of needs to be. All four bedrooms are on the second level up a handsome but very narrow staircase, and one is used as an office. They have restored leaded glass and lovely dark hardwood floors and trim.

The clipped lot—cut short by intersecting alleys—is just 91 feet deep but manages a three-car garage perfect for extra storage. There is no backyard since the garage is flush to the house, but the previous owner compensated for this loss by building a large garage-top roof deck accessed directly from the home’s second floor. Miniature side and front yards, one large contorting tree, and a koi pond lend enough space for a couple of loungers, but privacy is at a premium. There was an opportunity to buy the side alley from the city several years ago for $141,000—at the time, too costly. No new structures would’ve been allowed but it had great potential as a side yard. Instead, the city piloted its first “green alley” here using permeable pavement and recycled materials.

Price Points: “When I moved here we had a bunch of people living together helping with the mortgage,” says Oliva. “We’ve gotten older and set out in different directions, so it’s best for me to move on.” She tested the market last fall in the $800,000s and $900,000s but the current asking price is probably more reflective of the house’s size and irregularities.

The boulevards don’t offer a ton of single-family inventory since many of the larger houses have been subdivided and those that haven’t are highly coveted. A four-bed bungalow on Palmer Boulevard, smaller but with a large lot, sold March 1 for $630,000; a 4,000-square-foot gut-renovated five-bed on Logan Boulevard closed for $1.03 million last July; and, also in July, a stately Kedzie Boulevard address went for $1.675 million. Neither is a fair comp, but together they give an approximate range of boulevard single-families.

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