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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$1,250,000

5954 N Paulina Street, Chicago

5 Beds 3.5 Baths 3,900 SqFt Residential MLS® # 12754178

$1,250,000

21 E Huron Street 2102, Chicago

2 Beds 2.5 Baths 1,786 SqFt Residential MLS® # 12742473

New

$1,250,000

2948 W Belden Avenue, Chicago

3 Beds 3.5 Baths 2,400 SqFt Residential MLS® # 12742185

$1,250,000

↓ $35,000

1000 W Washington Boulevard 141, Chicago

3 Beds 2.5 Baths 3,500 SqFt Residential MLS® # 12722285

$1,250,000

333 W Menomonee Street, Chicago

3 Beds 2 Baths 0 SqFt Residential MLS® # 12705653

$1,250,000

515 W 28th Place, Chicago

5 Beds 4.5 Baths 0 SqFt Residential MLS® # 12700722

$1,250,000

1548 W Ardmore Avenue 2c, Chicago

5 Beds 3 Baths 3,018 SqFt Residential MLS® # 12699561

$1,250,000

↓ $150,000

4950 S Chicago Beach Drive 11a, Chicago

3 Beds 4.5 Baths 4,000 SqFt Residential MLS® # 12670499

$1,250,000

25 E Superior Street 3601, Chicago

3 Beds 3 Baths 2,610 SqFt Residential MLS® # 12658344

$1,250,000

221 E Walton Place 13c, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12580535

$1,249,900

↓ $50,100

1300 N Claremont Avenue 1e, Chicago

5 Beds 3 Baths 3,500 SqFt Residential MLS® # 12757486

$1,249,900

↓ $50,000

1000 W Washington Boulevard 406, Chicago

3 Beds 2 Baths 2,400 SqFt Residential MLS® # 12657871

$1,249,000

↓ $26,000

1639 W Rascher Avenue, Chicago

6 Beds 0 Baths 0 SqFt Residential Income MLS® # 12763197

New

$1,249,000

21 E Huron Street 3204, Chicago

3 Beds 3.5 Baths 0 SqFt Residential MLS® # 12748390

$1,249,000

↓ $50,000

60 E Monroe Street 6703, Chicago

2 Beds 2.5 Baths 1,999 SqFt Residential MLS® # 12719368

$1,247,500

4937 N Bell Avenue, Chicago

7 Beds 0 Baths 0 SqFt Residential Income MLS® # 12722849

New

$1,240,000

1617 W Grand Avenue 1w, Chicago

4 Beds 3 Baths 3,500 SqFt Residential MLS® # 12763953

$1,225,000

2729 N Southport Avenue 1, Chicago

4 Beds 2.5 Baths 0 SqFt Residential MLS® # 12747223

$1,225,000

222 N Columbus Drive 4703, Chicago

3 Beds 2.5 Baths 1,790 SqFt Residential MLS® # 12692152

Open House

$1,223,000

850 N Lake Shore Drive 1805, Chicago

2 Beds 2 Baths 1,737 SqFt Residential MLS® # 12640555

$1,215,000

↓ $10,000

800 N Michigan Avenue 4703, Chicago

2 Beds 2.5 Baths 2,000 SqFt Residential MLS® # 12707596

New Open House

$1,200,000

21 E Huron Street 1802, Chicago

2 Beds 2.5 Baths 1,786 SqFt Residential

Open House

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

MLS® # 12777153

$1,200,000

4623 S Prairie Avenue, Chicago

9 Beds 0 Baths 0 SqFt Residential Income MLS® # 12770130

New

$1,200,000

250 E Pearson Street 1903, Chicago

2 Beds 2.5 Baths 0 SqFt Residential MLS® # 12765630

$1,200,000

907 W Fullerton Avenue, Chicago

4 Beds 2.5 Baths 4,000 SqFt Residential MLS® # 12763740

$1,200,000

1205 W Montana Street 1w, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12754695

New

$1,200,000

2428 N Rockwell Street, Chicago

5 Beds 0 Baths 0 SqFt Residential Income MLS® # 12748261

New Open House

$1,200,000

925 N Larrabee Street 2s, Chicago

3 Beds 2 Baths 2,200 SqFt Residential

Open House

Sun, Oct 11th, 2026 @ 1pm - 3pm

MLS® # 12743765

New

$1,200,000

1314 W Carmen Avenue, Chicago

6 Beds 0 Baths 0 SqFt Residential Income MLS® # 12737730

$1,200,000

326 W Concord Place, Chicago

5 Beds 0 Baths 0 SqFt Residential Income MLS® # 12728454

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