$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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New Open House
3441 N Springfield Avenue, Chicago

$1,050,000

3441 N Springfield Avenue, Chicago

4 Beds 4 Baths 0 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 12:30pm
MLS® # 12779226

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New
3517 W Diversey Avenue, Chicago

$1,050,000

3517 W Diversey Avenue, Chicago

6 Beds 0 Baths 0 SqFt Residential Income MLS® # 12774977

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New
3847 N Spaulding Avenue, Chicago

$1,050,000

3847 N Spaulding Avenue, Chicago

5 Beds 0 Baths 0 SqFt Residential Income MLS® # 12768674

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Open House
2012 W Shakespeare Avenue 1, Chicago

$1,050,000

2012 W Shakespeare Avenue 1, Chicago

4 Beds 3 Baths 2,800 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 1pm
MLS® # 12767134

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1357 N Maplewood Avenue, Chicago

$1,050,000

1357 N Maplewood Avenue, Chicago

8 Beds 0 Baths 0 SqFt Residential Income MLS® # 12765710

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Open House
2837 N Halsted Street 2n, Chicago

$1,050,000

2837 N Halsted Street 2n, Chicago

3 Beds 2 Baths 1,650 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 1:30pm
MLS® # 12759219

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4426 N Damen Avenue, Chicago

$1,050,000

↓ $150,000

4426 N Damen Avenue, Chicago

7 Beds 0 Baths 0 SqFt Residential Income MLS® # 12757528

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1420 N Elk Grove Avenue 2, Chicago

$1,050,000

1420 N Elk Grove Avenue 2, Chicago

3 Beds 2 Baths 0 SqFt Residential MLS® # 12735512

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1757 W Sunnyside Avenue A, Chicago

$1,050,000

1757 W Sunnyside Avenue A, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12732237

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1310 N Ritchie Court 10ad, Chicago

$1,050,000

↓ $99,000

1310 N Ritchie Court 10ad, Chicago

3 Beds 3 Baths 3,000 SqFt Residential MLS® # 12717753

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57 E Delaware Place 1805, Chicago

$1,050,000

↓ $20,000

57 E Delaware Place 1805, Chicago

3 Beds 2.5 Baths 1,855 SqFt Residential MLS® # 12633258

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3422 S Normal Avenue, Chicago

$1,050,000

↓ $30,000

3422 S Normal Avenue, Chicago

3 Beds 4.5 Baths 3,500 SqFt Residential MLS® # 12574749

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1345 W Grand Avenue 4n, Chicago

$1,049,999

1345 W Grand Avenue 4n, Chicago

2 Beds 2 Baths 0 SqFt Residential MLS® # 12764213

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New
3432 W Cortland Street, Chicago

$1,049,914

3432 W Cortland Street, Chicago

12 Beds 0 Baths 0 SqFt Residential Income MLS® # 12740995

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1346 W Walton Street 3w, Chicago

$1,049,900

1346 W Walton Street 3w, Chicago

3 Beds 2 Baths 1,875 SqFt Residential MLS® # 12771126

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1833 N Larrabee Street 2, Chicago

$1,049,000

↓ $76,000

1833 N Larrabee Street 2, Chicago

2 Beds 2 Baths 1,352 SqFt Residential MLS® # 12760212

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1648 W Division Street 110, Chicago

$1,049,000

1648 W Division Street 110, Chicago

3 Beds 2.5 Baths 2,430 SqFt Residential MLS® # 12753491

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211 N Harbor Drive 3803, Chicago

$1,049,000

↓ $51,000

211 N Harbor Drive 3803, Chicago

2 Beds 2 Baths 1,408 SqFt Residential MLS® # 12750150

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401 N Wabash Avenue 44f, Chicago

$1,049,000

↓ $101,000

401 N Wabash Avenue 44f, Chicago

2 Beds 2.5 Baths 2,022 SqFt Residential MLS® # 12611596

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New
211 N Harbor Drive 2404, Chicago

$1,045,000

211 N Harbor Drive 2404, Chicago

2 Beds 2 Baths 1,251 SqFt Residential MLS® # 12780458

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211 N Harbor Drive 2304, Chicago

$1,040,000

211 N Harbor Drive 2304, Chicago

2 Beds 2 Baths 1,251 SqFt Residential MLS® # 12696896

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Open House
2847 N Damen Avenue 1, Chicago

$1,039,000

2847 N Damen Avenue 1, Chicago

3 Beds 3 Baths 0 SqFt Residential
Sun, Oct 11th, 2026 @ 12pm - 1:30pm
MLS® # 12760308

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Open House
850 N Lake Shore Drive 905, Chicago

$1,039,000

↑ $19,000

850 N Lake Shore Drive 905, Chicago

2 Beds 2 Baths 1,737 SqFt Residential MLS® # 12634291

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Open House
850 N Lake Shore Drive 1807, Chicago

$1,032,000

850 N Lake Shore Drive 1807, Chicago

2 Beds 2 Baths 1,402 SqFt Residential MLS® # 12586543

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New
6743 N Oliphant Avenue, Chicago

$1,025,000

6743 N Oliphant Avenue, Chicago

3 Beds 3.5 Baths 3,094 SqFt Residential MLS® # 12762657

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New Open House
2625 N Wilton Avenue 3, Chicago

$1,000,000

2625 N Wilton Avenue 3, Chicago

2 Beds 2 Baths 1,328 SqFt Residential
Sat, Oct 10th, 2026 @ 11:30am - 1:30pm
MLS® # 12769807

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2135 W Barry Avenue, Chicago

$1,000,000

2135 W Barry Avenue, Chicago

7 Beds 0 Baths 0 SqFt Residential Income MLS® # 12757614

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1908 W Cuyler Avenue, Chicago

$1,000,000

1908 W Cuyler Avenue, Chicago

6 Beds 0 Baths 0 SqFt Residential Income MLS® # 12757516

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New
4713 N Damen Avenue 1n, Chicago

$1,000,000

4713 N Damen Avenue 1n, Chicago

4 Beds 2.5 Baths 2,800 SqFt Residential MLS® # 12750584

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New
2331 N Wayne Avenue, Chicago

$1,000,000

2331 N Wayne Avenue, Chicago

3 Beds 2.5 Baths 2,400 SqFt Residential MLS® # 12749153

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Posted by Leo Clark. on

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