From the North Side all the way down to Hyde Park and South Shore, Chicago is home to hundreds of historic prewar apartment buildings located near the lakefront. In an era dominated by open-concept spaces lacking walls, these vintage spaces hold a certain romantic appeal for some buyers. So, what defines a prewar apartment? Essentially, it is any multi-unit residential building constructed before World War II, when layouts were more formal and featured clearly defined rooms. After the mid-1940s, designs became more open and modern, often without staff rooms and separate kitchens for live-in help. Beaux Arts, Tudor, and Georgian styles were among the more common of prewar designs, but some were also influenced by the emerging Art Deco style of the 1920s, as you’ll see with one of our listings. One architect stands out as the master of these buildings: Robert S. De Golyer, who designed three of our properties for sale. While condos in pre-war structures generally offer more overall space with their square footage (even if divided into individual rooms) and are constructed of solid materials, they do not align with today’s design trends. Despite the lower asking prices of some of our properties, they often come with high HOA fees, which might explain why they do not always sell immediately.
3750 N Lake Shore Dr APT 16H, $575,000
Our smallest listing, spanning 1,700 square feet, just so happens to be a two-bed, two-bath penthouse perched atop Robert S. De Golyer’s 1920s Beaux-Arts masterpiece on Lake Shore Drive, between Montrose and Belmont harbors. As described on the building’s website: “Enter any apartment…to appreciate how the rooms are placed in the order most favorable for their use. They take every possible advantage of their site on Lake Shore Drive. Their forms and dimensions are elegant, comfortable and useful.” It’s a full-service building, so the nearly $2,500 monthly HOAs include 24-hour door staff, a fitness center, indoor pool, and other amenities.
3530 N Lake Shore Dr APT 11B, $600,000
A few blocks away in the same East Lake View neighborhood stands this pre-war, Georgian building, constructed between 1922-24 and designed by architects Rissman & Hirschfield. The future owner of this two-bedroom, two-bathroom condo with $2,011 monthly HOAs is guaranteed privacy, as there are only two residences per floor. “Fully updated with designer finishes” since it sold last year, the unit features a grand foyer with doorways that lead to various interior spaces, including the combined living and dining rooms with views of the lake. The kitchen and bathrooms have all been remodeled. The primary suite has a spa-inspired bath with marble finishes and a window that overlooks the park and lake.
5000 S East End Ave APT 23A, $314,900
This historic pre-war 28-story condominium with limestone exterior was originally built in 1927 and designed by architect Robert S. De Golyer. Located on the 23rd floor, the nearly 2,000-square-foot property offers views of the Kenwood and Hyde Park neighborhoods, as well as Lake Michigan. This three-bedroom, three-bathroom condo has been lingering on the market since the summer. Despite a recent price reduction, which lowered the asking price to just over $300,000, the monthly HOAs of nearly $2,500 per month remain a significant consideration for why it hasn’t sold.
4950 S Chicago Beach Dr #4A, $350,000
The Art Deco-style Powhatan is another design by De Golyer, created with Charles L. Morgan, who was an associate of Frank Lloyd Wright. Spanning almost 4,200 square feet, this four-bed, four-bath unit in the 22-story building last sold over a decade ago, yet remains a true time capsule: from the vintage kitchen, featuring painted tile by artist Jane Dickerman done in the 1950s, to the multiple vintage bathrooms (Who doesn’t love pink? That avocado tile along with the elaborate wallpaper is amazing!). Naturally, the assessments are high ($6,653 per month to be exact). However, they cover exterior maintenance of the colorful mosaics, as well as the historic lobby, indoor swimming pool, and rooftop ballroom — and taxes, which are a pretty significant expense!
220 E Walton Pl #5E, $1,249,000
We conclude with a property located in the heart of the Gold Coast and Streeterville area, a historic pre-war Fugard & Knapp design from 1919 that blends Gothic Revival architecture with modern elements. The boutique building offers 19 residences, with just two units per floor. Just over 3,000 square feet, this four-bedroom, four-bathroom condo with nearly $3,000 monthly HOAs is certainly impressive, justifying its high price. It was also upgraded three years ago and now includes a high-efficiency Unico HVAC system, designer lighting, motorized bed shades, and a new LG washer and dryer.