Chicago recently ranked all 205 suburbs in the six-county Chicago area, and Highland Park was in the top 10. Incorporated as a city in March of 1869 with about 600 residents, a school, and a hotel, the town has certainly grown a lot since then. So what’s for sale here? Well, it’s not every day that a residence designed by modernist architects Keck & Keck hits the market, especially one that has never before been offered for sale. An official local landmark, the home is protected from demolition. Its secluded location close to the lake would otherwise have it vulnerable as a teardown. That home quickly went on and off market, but there’s lots more to find — including a house that has a connection to Edith Rockefeller McCormick.

829 Saint Johns Avenue Highland Park, $699,000

Photography by Melanie Wegner

This three-bedroom, two-bathroom house, spanning 1,900 square feet, has a charming exterior, but has been completely redone inside. I do love the enclosed entry porch, but I’m not sure how I feel about the openness of the new layout. Removing the walls has now opened up the staircase, which might not be to everyone’s liking, as now the office space is open to all the noise of the house. Even with the updates, the current owners didn’t install central air conditioning; there are only window units. But, perhaps, that’s not a major concern being close to the lake on the North Shore. The backyard is really lovely though, especially that paver stone patio.

1324 Golf Ave., Highland Park, $525,000

Photography by Vis-Home

Located on a dead-end street in the Briergate neighborhood that backs up to the 120-acre Sunset Valley Golf Club and the Skokie River, this Cape Cod-style home features three bedrooms, two full bathrooms, and a partially finished basement. The property last sold for $370,000 in 2004, reflecting a nearly 50% increase from its original asking price, though it has just been reduced by $25,000. The well-maintained home has a family room addition directly off the kitchen, with a vaulted ceiling and windows overlooking the large backyard. An EV car charger is included, a convenient amenity given the home’s proximity to Route 41 and the Edens/Interstate 94.

3107 Dato Ave., Highland Park, $725,000

Photography by One Bed Media

According to this bike tour map of historic homes put together by Highland Park’s Historic Preservation Commission, this Tudor Revival residence and its next-door neighbor were possibly the first model homes built by the Krenn-Dato Company in 1927-28. Obviously, the street was named after them, but unfortunately, the 1929 stock market crash and the Great Depression caused the termination of future construction plans for their new development. This nearly 2,000-square-foot, three-bedroom home, with its striking exterior half-timbering and dormer shapes, just sold a year ago and is being listed “as-is” by its owner. There is an offer to replace the original windows, bathrooms (do I spy pink tile?), and complete the unfinished basement for an additional $75,000-150,000.

3290 Brook Road, Highland Park, $1,375,000

Photography by Don Tinsley

Located just west of Sheridan Road, not far from our previous listing, sits a nearly 4,000-square-foot, five-bedroom residence on a little over half an acre of land. Just like the Keck & Keck design, this is another custom-built midcentury modern home, which was last on the market 10 years ago and is now looking for only its third owner since construction in 1969. What stands out here besides its architectural awesomeness? How about the exposed clinker brick, the sunken living room, the double-sided fireplace, and the floor-to-ceiling windows that help bring in the natural surroundings. And may I add that the outdoor space, with its patio, fire pit, and professional landscaping is truly a dream backyard.