Two penthouses just hit the market at the same time—one in Lincoln Park and the other in Gold Coast. They both sit atop 19th century landmarks, have more than 3,000 square feet, and are listed for more than $2 million. That's about where their similarities end, though. 

The first belongs to a retail and residential conversion of the 1888 40th police precinct building on Halsted Street near Webster Avenue, one of the oldest left in the city. It was only a precinct station until the 1930s and then became an American Legion Hall. Today a pilates studio takes the basement—right where the holding cells used to be—and the first level is vacant retail space. Gap did business here in the 1980s and 90s and the upper level was their storage. That ignoble use ended with All Access Group’s 2006 condo rebuild. The single unit, on the market for $2.2 million, has a whopping 4,000 square feet of living space on one level with 15-foot ceilings, impressively tall windows and doorways, and a cartoonish spiral staircase.

The building takes up two standard city lots, line to line, creating the enormous floor plates. Since the unit has sole possession of the nearly 50’ x 125’ roof, big things were inevitable in the right hands. When seller Andrew Benson, a trader and real estate investor, purchased the place in 2008 for $1.14 million he immediately set out to build a sensational spiral staircase to the roof and a 3,000-square-foot terrace designed to bring out the party animal in anyone. Everything you’d find at a swanky rooftop restaurant or bar is accounted for: cabanas; full bar; multiple flatscreen TVs; grills; chaise lounges; heaters; greenery; and a toilet. Oh, and a hot tub and shower for the hell of it. 

The stairs took a steelworker two months to construct and the Commission on Chicago Landmarks had to be satisfied that the roof terrace didn’t alter the historic sightlines from the street. To accomplish this, the deck had to be set back 10-12 feet from the front of the building.

Back inside, Benson also added an HD projection system and a wet bar. The couple of people who saw the listing in its first week were blown away by its proportions, says listing agent Luke Blahnik of Blahnik Properties. Two more showings are lined up in the next few days. Often such a large and personal space takes time to sell, but Blahnik feels good about the rooftop’s say in the matter. Based on the roof deck we’re probably looking at a young couple or an athlete… it rented to a Cubs player over the summer.” Blahnik wouldn’t say which player.

A decidedly more docile penthouse atop the Patterson-McCormick Mansion also just hit the market. The mansion, among the largest former single-family homes in the city, was built in 1893 by Chicago mayor and Tribune founder Joseph Medill as a gift for his daughter Elinor and her husband, Robert Wilson Patterson, Jr. Decades later, Cyrus Hall McCormick, Jr. purchased the mansion. Cyrus, Sr. trademarked the reaper and cashed in.

Converted to condos in 1978, the regal lobby and main stairs preserve the feeling that you’re in the company of titans of industry. The classical finishes of most of the building’s nine units (six condos and three attached town homes, one belonging to Billy Corgan until early 2013) further this experience, but the listed penthouse takes a turn toward the modern.

Shirley Young paid $1.25 million for the 3,000-square-foot duplex space in 2008, with three en suite bedrooms. Now looking to downsize, she leaves the unit in better shape than she found it: the HVAC system, light fixtures, windows, kitchen, and bathrooms are all new. A mosaic backsplash, large skylight, and pastel stools and counters make the eat-in kitchen a crisp and almost weightless space, and blue-and-white mosaic has a similar effect on the bathrooms.

What Young did to the walls and ceilings stands out most. The material is recycled linoleum plaster and the surfaces are rubbed in beeswax. It creates sheen without the use of paint that “captures reflections of the tree canopy,” says Young. It glistens at every angle, in fact, and to the touch feels a lot like lacquer cabinetry. I’ve never seen this treatment before, but Young informs me the practice is derived from Italy where it is much more common.

Young also covered one of two living room fireplaces with a wall of built-in bookshelves. For outdoor space, the comfortable back terrace isn’t much of a candidate for a GQ shoot; it’s really just an asset for everyday life. Sandra Matson of Baird & Warner has the listing. The asking price? $2 million.