Chicagoland Luxury Home Sales Continue to Soar

In a blockbuster year for the upper-end housing market in Chicagoland, Crain’s Chicago Business reports there have been a record-setting 104 homes that have sold for $4 million or more in the first three quarters of 2022. Strong price appreciation over the past 2+ years has motivated sellers to list their homes. Meanwhile, luxury buyers have been undeterred by rising mortgage interest rates, often choosing to pay cash. Christie’s International Real Estate reported on this trend in its 2022 Luxury Trends Report, noting that high inflation and stock market volatility have also prompted affluent buyers to move money into hard assets like real estate.

While inventory remains historically low, luxury buyers from the city to the North Shore to the western suburbs still have plenty of options to take lavish living to the next level. Here is a sampling of what is currently available to upper-bracket buyers.

445 Sheridan Rd. – Winnetka, IL – $15,850,000

Winnetka accounts for 10 home sales over $5 million this year – already double last year’s total. This lakefront estate in the tony North Shore suburb is another listing that could keep that figure climbing. Sitting on 2.2 acres with over 165 feet of Lake Michigan shoreline, the Spanish-influenced villa will have you feeling like you’ve escaped to an exclusive resort. The manicured grounds feature the main residence, plus a two-story cabana house, pool, and fountain. The lake side of the property has a sweeping terrace and steps leading down the private beach. And that’s just the outside.

Inside, the grand foyer entrance allows for picturesque views of the lake with a double atrium staircase accented with braided columns, matching arched cases, and fireplace. The home’s four levels are all accessible by elevator, and on the lower level, a surprise awaits: a hidden speakeasy bar with an intricately painted undulating ceiling. This historic five-bedroom, five-full bath, four-half bath estate is ready for its next chapter to be written.


337 N. Deere Park Dr. East – Highland Park, IL – $6,800,000

Built in 2007, this contemporary showstopper has floor-to-ceiling windows with views of Lake Michigan from every main room. Outfitted with top-of-the-line appliances and limestone counters, the kitchen also has views of the outdoor patio and lake. The first floor features a guest bedroom and full bath, while the remaining five bedrooms, including a luxe primary suite, are on the second floor. The third floor has a multi-purpose space with an outdoor deck overlooking the lake. Other features of the home include a large lower-level family room, a half basketball court, abundant storage, an elevator, and a three-car garage.


2238 N. Dayton St. – Chicago, IL – $5,900,000

This extra-wide single-family residence is an exceptional opportunity in the heart of Lincoln Park. In addition to 8,000 square feet of living space including six bedrooms, seven full bathrooms and a half-bath, the home boasts a backyard patio, lawn, rooftop deck, and three-car garage. Full of character, this updated beauty has all the amenities of new construction with the charm of an older home – including a limestone fireplace, oversized windows with stained glass detailing, crown moldings, and pocket doors. A traditional butler’s pantry connects a spacious kitchen to a large dining room for easy entertaining. The home is also equipped with a full mudroom with storage, as well as a lower-level wine cellar. A rare find in the city, this home will offer its new residents a quiet, tree-lined street in a sought-after neighborhood just steps from parks, shopping, and dining.


323 Hillcrest Ave. – Hinsdale, IL – $4,999,000

Stately is the perfect word to describe this 12,076 square foot Hinsdale mansion. Situated on 1.8 acres, the sprawling Georgian Colonial features one of the largest lots in the area. The home has been completely renovated and impeccably maintained with modern conveniences including a state-of-the-art chef’s kitchen. All four levels are accessible by elevator. In addition to six bedrooms, eight bathrooms, three half baths, and fireplaces throughout, the home has a guest house and pool surrounded by blue stone tile and lush landscaping. A wood-paneled office, traditional billiard room, second kitchen in the lower-level guest quarters and five-car garage further add to the opulence of this Southeast Hinsdale compound.


275 S. Arlington Ave. – Elmhurst, IL – $4,250,000

Amenities abound in this 8,303-square-foot newer construction home. A library, custom built-in bar, theater, wine cellar, gym, playroom, billiard area, vaulted ceilings, and four-car heated garage are just some of the extras that make this residence an epic find. Five bedrooms upstairs, a guest suite on the main level, five full baths and two half baths contribute to the expansive space in this modern home filled with every imaginable convenience. The outdoor space has been updated to include an oversized patio complete with a built-in Wolf grill, Sub Zero refrigerator and fire pit – with plenty of yard remaining for a potential play area or pool. Chances are you won’t want to leave the comfort of this suburban palace, but when you do, you’ll be within walking distance of town.

For more information on these listings or other homes in Chicago, visit and reach out to your @properties Christie’s International Real Estate agent.

Written by @properties
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