$10+ Million Real Estate For Sale in Downtown Chicago

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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6418 S Vernon Avenue, Chicago

$1,299,900

↓ $25,100

6418 S Vernon Avenue, Chicago

14 Beds 0 Baths 0 SqFt Residential Income MLS® # 12741726

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550 N Kingsbury Street 610, Chicago

$1,299,900

550 N Kingsbury Street 610, Chicago

4 Beds 3 Baths 2,450 SqFt Residential MLS® # 12740917

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2725 N Wayne Avenue 1, Chicago

$1,299,000

2725 N Wayne Avenue 1, Chicago

4 Beds 2.5 Baths 0 SqFt Residential MLS® # 12771517

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3754 W Sunnyside Avenue, Chicago

$1,299,000

3754 W Sunnyside Avenue, Chicago

4 Beds 3.5 Baths 3,800 SqFt Residential MLS® # 12753249

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1400 W Monroe Street 2b, Chicago

$1,299,000

↓ $51,000

1400 W Monroe Street 2b, Chicago

3 Beds 2.5 Baths 1,846 SqFt Residential MLS® # 12750295

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New
1736 W Beach Avenue, Chicago

$1,299,000

1736 W Beach Avenue, Chicago

6 Beds 0 Baths 0 SqFt Residential Income MLS® # 12741301

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1955 N Halsted Street 2, Chicago

$1,299,000

1955 N Halsted Street 2, Chicago

3 Beds 2 Baths 1,830 SqFt Residential MLS® # 12687036

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New
2127 N Winchester Avenue, Chicago

$1,299,000

2127 N Winchester Avenue, Chicago

4 Beds 0 Baths 0 SqFt Residential Income MLS® # 12684082

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1513 W Addison Street, Chicago

$1,299,000

1513 W Addison Street, Chicago

8 Beds 0 Baths 0 SqFt Residential Income MLS® # 12666976

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New
840 N Lake Shore Drive 1002, Chicago

$1,299,000

840 N Lake Shore Drive 1002, Chicago

2 Beds 2.5 Baths 2,540 SqFt Residential MLS® # 12637619

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New
161 E Chicago Avenue 24-02, Chicago

$1,295,000

161 E Chicago Avenue 24-02, Chicago

2 Beds 2.5 Baths 2,000 SqFt Residential MLS® # 12770886

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900 W Washington Boulevard 301, Chicago

$1,295,000

900 W Washington Boulevard 301, Chicago

2 Beds 2.5 Baths 1,605 SqFt Residential MLS® # 12755155

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New
420 W Ontario Street 405, Chicago

$1,295,000

420 W Ontario Street 405, Chicago

4 Beds 4 Baths 3,500 SqFt Residential MLS® # 12753902

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1501 N State Parkway 12c, Chicago

$1,295,000

1501 N State Parkway 12c, Chicago

2 Beds 2 Baths 1,850 SqFt Residential MLS® # 12730093

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9101 S Hoyne Avenue, Chicago

$1,295,000

↓ $80,000

9101 S Hoyne Avenue, Chicago

6 Beds 6 Baths 5,042 SqFt Residential MLS® # 12690357

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2832 N Mozart Street, Chicago

$1,295,000

2832 N Mozart Street, Chicago

8 Beds 0 Baths 0 SqFt Residential Income MLS® # 12621086

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310 S Michigan Avenue 1705, Chicago

$1,295,000

310 S Michigan Avenue 1705, Chicago

3 Beds 3.5 Baths 2,706 SqFt Residential MLS® # 12621004

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340 E Randolph Street 5504, Chicago

$1,295,000

340 E Randolph Street 5504, Chicago

2 Beds 2.5 Baths 1,902 SqFt Residential MLS® # 12391514

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4127 N Ashland Avenue, Chicago

$1,279,000

↓ $20,000

4127 N Ashland Avenue, Chicago

8 Beds 0 Baths 0 SqFt Residential Income MLS® # 12696276

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New Open House
24 E Scott Street 2, Chicago

$1,275,000

24 E Scott Street 2, Chicago

3 Beds 2.5 Baths 2,600 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 2pm
MLS® # 12778834

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New
3248 N Oakley Avenue, Chicago

$1,275,000

3248 N Oakley Avenue, Chicago

8 Beds 0 Baths 0 SqFt Residential Income MLS® # 12737803

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6224 N Keystone Avenue, Chicago

$1,275,000

6224 N Keystone Avenue, Chicago

5 Beds 3.5 Baths 3,950 SqFt Residential MLS® # 12721216

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New
234 W Polk Street 3908, Chicago

$1,270,000

234 W Polk Street 3908, Chicago

3 Beds 2 Baths 1,517 SqFt Residential MLS® # 12756111

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New
1235 N Damen Avenue, Chicago

$1,269,000

1235 N Damen Avenue, Chicago

4 Beds 3 Baths 2,912 SqFt Residential MLS® # 12766467

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New Open House
513 W 28th Place, Chicago

$1,250,000

513 W 28th Place, Chicago

5 Beds 4.5 Baths 0 SqFt Residential
Sun, Oct 11th, 2026 @ 11am - 12:30pm
MLS® # 12779964

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New
155 N Harbor Drive 3301-3302-3314, Chicago

$1,250,000

155 N Harbor Drive 3301-3302-3314, Chicago

3 Beds 3.5 Baths 2,743 SqFt Residential MLS® # 12766825

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Open House
1355 N Dean Street 1w, Chicago

$1,250,000

1355 N Dean Street 1w, Chicago

4 Beds 2.5 Baths 0 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 2pm
MLS® # 12765951

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New
363 W Superior Street B, Chicago

$1,250,000

363 W Superior Street B, Chicago

3 Beds 3.5 Baths 3,300 SqFt Residential MLS® # 12761964

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New
915 W Lawrence Avenue, Chicago

$1,250,000

915 W Lawrence Avenue, Chicago

5 Beds 3.5 Baths 2,950 SqFt Residential MLS® # 12761851

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5650 S Dorchester Avenue 1, Chicago

$1,250,000

5650 S Dorchester Avenue 1, Chicago

5 Beds 2.5 Baths 4,561 SqFt Residential MLS® # 12758344

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Posted by Leo Clark. on

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