Chicago Real Estate News & Neighborhood Notes

Since the record breaking sale of the penthouse at Trump Tower Chicago, it’s been a little while since we’ve checked in on some of downtown Chicago’s most expensive properties on the market.

As of today, just 10 listings are currently active on the Chicago real estate market for $10 million and over—appropriately enough—and as you can see below, some like the single-family mansion at 1547 N. Dearborn and the penthouse at 189 E. Lake Shore Drive are relatively familiar to those of us working in the industry every day, while others like the 7,100 square foot, full-floor condo at 9 W. Walton only just recently hit the MLS®.

Despite the luxury market being extremely hot right now in Chicago, when dealing with this sort of price level, it’s of course common for these and other ultra high-end properties to sit on the market a bit longer. But given the appeal, desirability, and overall spectacular nature that basically all of Chicago’s most expensive homes and condos offer, you never know when somebody might swoop in and make that life-changing investment.

For more information about luxury real estate in Downtown Chicago or to schedule a private showing for one the city’s elite property listings, contact one of our luxury home experts today at (312) 280-9600!

$10+ Million MLS® Listings Available in Chicago Right Now

Search $10+ Million MLS® Listings in Chicago, Over $1,000,000

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• Over $1,000,000

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$5,595,000

441 W Deming Place, Chicago

5 Beds 4.5 Baths 5,664 SqFt Residential MLS® # 12740927

$5,250,000

3026 N Lake Shore Drive, Chicago

6 Beds 8 Baths 9,100 SqFt Residential MLS® # 12737336

$5,250,000

3523 N Bosworth Avenue, Chicago

7 Beds 8 Baths 7,100 SqFt Residential MLS® # 12619988

New

$5,200,000

451 W Deming Place, Chicago

6 Beds 5 Baths 5,245 SqFt Residential MLS® # 12760503

$5,200,000

1515 N North Park Avenue, Chicago

7 Beds 5.5 Baths 8,400 SqFt Residential MLS® # 11755660

New

$5,000,000

920 W Monroe Street 1801, Chicago

3 Beds 3.5 Baths 3,657 SqFt Residential MLS® # 12777622

$4,995,000

1524 N Astor Street, Chicago

3 Beds 5 Baths 6,500 SqFt Residential MLS® # 12753134

$4,995,000

1109 W Washington Boulevard Ph8d, Chicago

5 Beds 4.5 Baths 5,110 SqFt Residential MLS® # 12676725

$4,995,000

1019 N Wolcott Avenue, Chicago

6 Beds 0 Baths 0 SqFt Residential Income MLS® # 12668130

New

$4,900,000

1447 N Dearborn Street 1n, Chicago

4 Beds 4.5 Baths 5,215 SqFt Residential MLS® # 12733434

$4,900,000

159 E Walton Place 28a, Chicago

3 Beds 2.5 Baths 5,400 SqFt Residential MLS® # 12654631

$4,800,000

363 E Wacker Drive 3101, Chicago

4 Beds 4 Baths 4,831 SqFt Residential MLS® # 12566071

$4,795,000

453 W Briar Place Ph-west, Chicago

5 Beds 5.5 Baths 0 SqFt Residential MLS® # 12594762

Open House

$4,695,000

1407 N Hoyne Avenue, Chicago

5 Beds 5.5 Baths 8,250 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 1pm - 3pm

MLS® # 12639287

$4,600,000

1455-59 N Sedgwick Street, Chicago

10 Beds 0 Baths 0 SqFt Residential Income MLS® # 12556436

$4,550,000

1734 N Wolcott Avenue, Chicago

6 Beds 7 Baths 6,000 SqFt Residential MLS® # 12612045

$4,500,000

435 N Michigan Avenue 2601, Chicago

2 Beds 2.5 Baths 0 SqFt Residential MLS® # 12684705

$4,495,000

21 N May Street 1103, Chicago

3 Beds 3.5 Baths 3,395 SqFt Residential MLS® # 12665090

$4,495,000

1811 N Howe Street, Chicago

5 Beds 4.5 Baths 5,900 SqFt Residential MLS® # 12595802

$4,350,000

363 E Wacker Drive 5801, Chicago

3 Beds 3 Baths 3,725 SqFt Residential MLS® # 11910436

New

$4,300,000

2119 N Seminary Avenue, Chicago

6 Beds 6.5 Baths 5,200 SqFt Residential MLS® # 12716177

$4,300,000

199 E Lake Shore Drive 8w, Chicago

3 Beds 3.5 Baths 4,000 SqFt Residential MLS® # 12623439

$4,300,000

435 N Michigan Avenue 1112, Chicago

4 Beds 3.5 Baths 3,444 SqFt Residential MLS® # 12454488

New

$4,250,000

920 W Monroe Street 504, Chicago

4 Beds 3.5 Baths 3,640 SqFt Residential MLS® # 12777609

$4,250,000

159 E Walton Place 22a, Chicago

3 Beds 4 Baths 5,500 SqFt Residential MLS® # 12677656

New

$4,200,000

1217 W Montana Street, Chicago

6 Beds 5 Baths 5,200 SqFt Residential MLS® # 12771589

$4,100,000

1447 N Dearborn Street 3n, Chicago

4 Beds 3.5 Baths 4,273 SqFt Residential MLS® # 12733402

New Open House

$4,000,000

1907 W Cuyler Avenue, Chicago

4 Beds 6.5 Baths 6,170 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 11am - 1pm

MLS® # 12774050

$4,000,000

111 S Peoria Street Ph03, Chicago

3 Beds 3.5 Baths 3,701 SqFt Residential MLS® # 12729476

$4,000,000

2719 N Dayton Avenue, Chicago

6 Beds 6.5 Baths 5,200 SqFt Residential MLS® # 12489324

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• Luxury Chicago Real Estate (36)
• Luxury Chicago Condos (14)