Price: $895,000

The landmarked Donohue Building and Annex at 711-727 S Dearborn Street was a linchpin of Chicago’s early 20th century publishing boom. More recently, it was key to Printer’s Row’s flip to residential in the 1980s and 90s. As the historic plaque tells it, the main wing of the Donohue “became the first of the city’s factory lofts to undergo conversion into condominium” in 1979. The Annex, where we find today’s monstrous property, followed suit in 1986.

Ironically, the sellers Bing and Linda O’Meara bought unit 812 in the Donohue Annex in 2003 not as a place to live, but for the purpose of publishing their magazine, Lakeland Boating. It took them years to find the right live/work area. “I wanted a place where I could take my dog to work, and you can’t do that anywhere up north,“ says Bing. “And I don’t like commercial property. I just don’t like the squareness of it.”

The condo covers 3,500 square feet, making it one of the Annex’s largest. Unlike the 1883 parent structure’s timber floors and pillars, everything in the 1913 Annex is brick and concrete, and it's virtually soundproof. Numerous large windows and 10.5-foot ceilings open up three exposures. Most 8^th floor spreads downtown don’t claim commanding views, but this one has straight-on views of Old Dearborn Station and the South Loop beyond, as well as the close-up warehouse context that attracts people to Printer's Row in the first place.

Many of the loft’s elegant treatments—from the terra cotta kitchen and dining room flooring and the custom chef’s kitchen itself, to the curvature of interior walls and dividers—date to a previous owner who kept a law practice onsite. The O’Mearas kept up the dignified look, also enhanced by hardwood floors and sturdy furniture.

Depending on a future owner’s plans, there are a couple of snags in layout. The space is currently fitted with just one proper four-walled bedroom, though curtains partition off another two potential bedrooms. The bedroom had been nanny quarters, also for a previous owner, and it creates some weirdness in the layout in that the enormous master bathroom is flung to the opposite end of the unit—attached to no dedicated bedroom.

That was fine for the O’Mearas' use as an office—their primary residence is on the North Shore. But that long hour and a half commute, plus a sense that real estate is heating up in prime city areas, led them to decide to sell. “Publishing has changed, and the marine industry, while strong at the moment, goes up and down,” adds Linda.

The Donohue and Annex sound more stable by comparison—very few of its properties became distressed in the recession.

Price Points: The loft was briefly listed in late 2009 for $869,000, but otherwise hasn’t seen the light of day since 2003, when it sold to the O’Mearas for $718,000. Homeowner dues are $1,824/month.

Linda acknowledges the sticker shock, but emphasizes the roles played by building age, responsive janitorial and maintenance staff, the vintage birdcage elevator, and the inclusion of heating in inflating the assessment. "The tradeoff, we feel, is worthwhile between a higher assessment and not having to deal with problems that arise in newer and far less sturdy buildings—things like construction noise [from neighbors and the outside world].”

Parking spaces are leased a la carte and start at $200/month. Coldwell Banker’s Jenny Ames has the listing. One comp in the building, slightly larger at 4,000 square feet but far clumsier, has been on the market since August 2011 and is asking $888,800.