Chicago Luxury Real Estate

By The Numbers: Chicago's Biggest Sales of 2023

Craig Hogan | January 4, 2024

The Top Residential Sales of 2023 

By any standard the numbers were strong however not enough to outshine the results from 2022. Both in volume and units, Chicago’s luxury residential market in 2023 dropped considerably from previous years. Inventory concerns mixed with interest rate drama, local and global unrest created a sometimes challenging scenario that follows the boom seen in 2020. If it's true that Chicago is "the pulse of America" the last year was telling for many. While it's still too early to forecast 2024 with accuracy, it could be that we're off to a good start if the uptick in pending sales keeps tracking. As others have pointed out, a hold over from last year at One Chicago is still pending and could be the leader for a strong 2024. As reported in @TRDChicago the #1 2023 sale marks a 39 percent decrease from the previous year’s top spot: the $20.6 million sale of a penthouse at the St. Regis. 


691 Sheridan Road, Winnetka | $12.5M

The 12,500-square-foot home in Winnetka sold for $1,000 per square foot. The five-bedroom, seven-bathroom home was built in 2005 and sits on Lake Michigan beachfront. Jena Radnay with @properties Christie’s International Real Estate represented the sellers, and Edward Gobbo with Berkshire Hathaway HomeServices Chicago represented the buyers: 

445 Sheridan Road, Winnetka | $12.25M

The 6,000-square-foot home, sold for over $2,000 per square foot, was built in 1918 and sits on over 2 acres on Lake Michigan. The home was designed with old-school entertaining in mind and originally included a ballroom. The property includes an elevator, speakeasy-style cocktail bar in the basement, and a sauna. The property also has a two-story cabana with its own elevator, a custom bar and two full kitchens.

800 North Michigan Avenue, Penthouse 66, Chicago | $11.2M

The property closed for $1,400 per square foot in January. It sold at a 25 percent loss for the seller who purchased the five-bedroom, 8,000-square-foot unit for $15 million in 2012. The home was listed by Susan Miner with Premier Relocation and Katherine Malkin of Compass represented the buyers.

1956 North Orchard Street, Chicago | $10.6M

This home sold for almost $964 per square foot after a $2 million cut to its asking price made in May. The seven-bedroom, 11,000-square-foot home was built in 2001 and renovated in 2020. The property was built on three city lots and includes a rare-for-the-city side yard. It features a three-story staircase atrium, a mud room, pet shower and outdoor half basketball court. The home was listed by Suzanne Gignilliat with @properties Christie’s International Real Estate, and Sharyl Mackey of Baird & Warner represented the buyer.

1100 North Lake Shore Drive, Unit 40B, Chicago | $6.8M

This penthouse sold in an off-market deal for $850 per square foot in May. The condo was originally three units that were previously assembled into an 8,000-square-foot condo. The property was listed by Julie Busby and Pamela Moran of Compass, and Lisa Finks and Diana Radosta of Compass represented the buyer. 

363 East Wacker Drive, #6306, Chicago | $6.5M

The St Regis residential tower dominated 2022’s list of priciest residential deals. A $20.6 million penthouse set a record for the highest priced residential sale in Chicago.  This four-bedroom, 4,800-square-foot condo on the 63rd floor sold for a little over $1,350 per square foot in May. Leila Zammatta with Magellan Realty LLC represented the developer, and Danielle Dowell and Jaclyn Kelly with Berkshire Hathaway HomeServices Chicago represented the buyers.

54 East Scott Street, Chicago | $6.5M

A rare contemporary home in Chicago’s Gold Coast sold for $625 per square foot. The 10,400-square-foot, five-bedroom home was built in 2010. The home includes an elevator, private outdoor space, and an attached 5-car garage with a gated driveway. Engel & Voelkers broker Jenny Ames represented the seller and Mark Icuss with Compass represented the buyers, who were not identified in public records. It closed at a significant price cut from the $9.4 million it originally sought when it hit the market in the spring of 2022.

2026 North Mohawk Street, Chicago | $6.3M

This home sold for $572 per square foot. The 11,000-square-foot, seven bedroom Lincoln Park home was listed by Emily Sachs Wong of @properties Christie’s International Real Estate. Susan Miner with Premier Relocation represented the buyer.

451 East Grand Avenue, #5909, Chicago | $6.35M

This condo at One Bennett Park sold for about $1,270 per square foot over the summer, after less than a month on the market. Built in 2019, the 5,000-square-foot condo has four bedrooms and five bathrooms. One Bennett Park is in the Streeterville neighborhood and has 69 stories. The condo was listed by Bradley Brondyke and R. Matt Leutheuser with Jameson Sotheby’s International Realty, and Elizabeth Ballis and Deborah Ballis Hirt of Compass represented the buyer.

325 Shoreline Court, Glencoe | $6.25M

Designed by architect Tony Grunsfeld and built in 1997, sold for a little over $1,000 per square foot. The 6,000-square-foot house is on Lake Michigan, with views of the lake throughout the home and 130 feet of lake frontage. Radnay of @properties Christie’s International Real Estate represented the buyers and sellers.

In the end... the 2023 luxury market witnessed noteworthy price adjustments across its pinnacle. Dispelling the misconception that the affluent remain impervious to market fluctuations, those who dared to challenge this notion experienced a stark reality check. Myself included. While certain sectors in the Chicago market outperformed, the most influential market segments fell short of anticipated levels. Properties languishing for well over a year, some even longer, ultimately fetched prices that were 50% or more below their initial listings, imparting a cautionary narrative. This serves as a reminder that, despite the seeming anomaly, markets require healthy fluctuations. 

In the realm of real estate, where language is defined by data and figures, I am optimistic for a more prosperous 2024.



This top 10 list appears in and sourced via The Real Deal Chicago @TRDChicago @mirandadavis @adamfarence

The commentary is my own. 


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