While browsing real estate listings, sometimes it’s fun to see what pops up when playing around with the various features on Zillow. Like when you type in keywords “first time on the market” or “only owner.” It’s a good way to not just narrow results but also discover fresh properties located throughout Chicagoland. And by fresh, I mean these buildings have never been for sale since they were initially constructed, or haven’t been available in several decades. Right now there are some interesting residences that fall perfectly into this category, like an architect’s own home in the Northwest suburbs, a famous Mies van der Rohe design, and an entire four-flat in Lake View. 

415 W Surf St, Chicago, $4,599,000

It is not every day that you find a property on the open market for the first time in more than a half century. This 1910 four-flat with a Flemish and English-bond brick facade and ornate ironwork in East Lake View is extra special for two reasons. Not only is the whole building for sale (a total of almost 15,000 square feet) but it’s a time capsule with nearly intact historic interiors that’s a mix between Art Nouveau and the Prairie School. Three of the apartments have beautiful elements like art glass windows and curving forms in the pocket doors. Architect Samuel N. Crowen, best known for the Biograph Theater, designed a number of handsome apartment blocks with similar detailing around the city. 

313 Longacres Ln, Palatine, $435,000

The home of local architect Roy Paleta, who died at the age of 90 this past September, has everything you’d expect to find in a midcentury modern design from 1960. Located on a half acre in suburban Palatine, the J-shaped, one-story brick ranch is built around a courtyard. Its southern exposure helps bring lots of natural light into the home. The house’s most unique feature is the galley kitchen with angled wood cabinets. Just two weeks after it was first listed, the three-bedroom, two-bathroom residence is already contingent.

8118 Edgewater Rd, Riverside, $500,000

It’s hard to believe a house could be kept in the same family for almost a century, but that’s exactly what happened with this storybook-style cottage in North Riverside. On the market for the first time since its original construction in 1933, the home’s two owners of the same family have preserved many of its historic details like the textured ornamental plaster walls and ceilings, hardwood floors, custom built-ins, and stone fireplaces in the living room and wood-paneled basement. Whimsical designs were all the rage in the 1920s and 30s, so this residence is like truly stepping back in time to yesterday’s trends. It’s close to attractions like McCormick Woods and the Brookfield Zoo.

860 N Lake Shore Dr APT 26K, Chicago, $950,000

When architect Mies van der Rohe arrived in Chicago from Germany in 1938, he’d leave a lasting impact on the city’s architectural landscape. One of his best known designs is the commission for 860-880 Lake Shore Drive, a pair of steel-and-glass towers built in 1951 that introduced his trademark of the curtain wall. A penthouse with floor-to-ceiling views of Lake Michigan and Navy Pier is available in the landmark cooperative building for the first time in 40 years. Since it was originally listed for sale in January, the price of this three-bedroom, three-bathroom unit has been significantly reduced to less than a million dollars (but HOA monthly fees are $3,687).

5320 S University Ave, Chicago, $2,750,000

Just because a home hits the market for the first time ever doesn’t mean it’s an older building. Sometimes you’ll come across a house built in the 21st century, such as this custom design “dream home” by local architect Scott A. Rappe, currently for sale by its only owners. Although located on a block full of historic structures in Chicago’s Hyde Park, the 2004 home still has plenty of curb appeal. The angular brick facade is accented by mahogany and weathered zinc. Inside the five-bedroom, five-bathroom residence, you’ll see the curved theme continues with various shapes in the walls, floors, room shapes, and even the staircase. More than 6,000 square feet of living space is spread through four levels, which will cost you almost $3 million.