$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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6638 S Woodlawn Avenue, Chicago

$1,200,000

6638 S Woodlawn Avenue, Chicago

11 Beds 0 Baths 0 SqFt Residential Income MLS® # 12726785

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3518 W Cortland Street 1, Chicago

$1,200,000

↓ $99,000

3518 W Cortland Street 1, Chicago

3 Beds 3.5 Baths 3,437 SqFt Residential MLS® # 12721332

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2040 W Charleston Street, Chicago

$1,200,000

2040 W Charleston Street, Chicago

8 Beds 0 Baths 0 SqFt Residential Income MLS® # 12688343

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6 N Bishop Street 206, Chicago

$1,200,000

6 N Bishop Street 206, Chicago

3 Beds 2 Baths 0 SqFt Residential MLS® # 12660925

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1908 S Loomis Street, Chicago

$1,200,000

↓ $200,000

1908 S Loomis Street, Chicago

9 Beds 0 Baths 0 SqFt Residential Income MLS® # 12603566

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3736 S Michigan Avenue, Chicago

$1,200,000

3736 S Michigan Avenue, Chicago

8 Beds 10 Baths 11,108 SqFt Residential MLS® # 12580025

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3231 N Octavia Avenue, Chicago

$1,200,000

3231 N Octavia Avenue, Chicago

6 Beds 3.5 Baths 4,000 SqFt Residential MLS® # 12493815

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New Open House
4217 S Indiana Avenue, Chicago

$1,199,999

4217 S Indiana Avenue, Chicago

9 Beds 0 Baths 0 SqFt Residential Income
Sat, Oct 10th, 2026 @ 1pm - 2pm
MLS® # 12768124

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2821 W Walnut Street, Chicago

$1,199,999

2821 W Walnut Street, Chicago

9 Beds 0 Baths 0 SqFt Residential Income MLS® # 12752232

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1812 W Erie Street, Chicago

$1,199,999

1812 W Erie Street, Chicago

8 Beds 0 Baths 0 SqFt Residential Income MLS® # 12749625

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6732 N Oxford Avenue, Chicago

$1,199,900

6732 N Oxford Avenue, Chicago

5 Beds 3.5 Baths 3,700 SqFt Residential MLS® # 12761721

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1730 N Wilmot Avenue, Chicago

$1,199,900

1730 N Wilmot Avenue, Chicago

2 Beds 3 Baths 2,600 SqFt Residential MLS® # 12760765

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5100 N Long Avenue, Chicago

$1,199,900

↓ $65,000

5100 N Long Avenue, Chicago

6 Beds 3.5 Baths 5,000 SqFt Residential MLS® # 12754087

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Open House
1540 N North Park Avenue 3s, Chicago

$1,199,900

1540 N North Park Avenue 3s, Chicago

3 Beds 2 Baths 0 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 2pm
MLS® # 12738427

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New Open House
942 W Hubbard Street, Chicago

$1,199,000

942 W Hubbard Street, Chicago

4 Beds 3.5 Baths 0 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 1pm
MLS® # 12779135

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New
2481 N Milwaukee Avenue 401, Chicago

$1,199,000

2481 N Milwaukee Avenue 401, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12775359

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New
3244 W Potomac Avenue, Chicago

$1,199,000

3244 W Potomac Avenue, Chicago

5 Beds 0 Baths 0 SqFt Residential Income MLS® # 12773705

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2321 W Belden Avenue 1, Chicago

$1,199,000

2321 W Belden Avenue 1, Chicago

3 Beds 2.5 Baths 3,105 SqFt Residential MLS® # 12772117

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425 W Briar Place 1e, Chicago

$1,199,000

↓ $51,000

425 W Briar Place 1e, Chicago

5 Beds 3 Baths 3,700 SqFt Residential MLS® # 12765537

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New
3657 N Hermitage Avenue, Chicago

$1,199,000

3657 N Hermitage Avenue, Chicago

5 Beds 0 Baths 0 SqFt Residential Income MLS® # 12758512

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30 W Erie Street 501, Chicago

$1,199,000

↓ $51,000

30 W Erie Street 501, Chicago

3 Beds 2.5 Baths 2,775 SqFt Residential MLS® # 12695714

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Open House
850 N Lake Shore Drive 1605, Chicago

$1,199,000

↑ $19,000

850 N Lake Shore Drive 1605, Chicago

2 Beds 2 Baths 1,737 SqFt Residential MLS® # 12588487

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New
6109 S Greenwood Avenue, Chicago

$1,198,988

6109 S Greenwood Avenue, Chicago

8 Beds 0 Baths 0 SqFt Residential Income MLS® # 12749117

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3762 S Indiana Avenue, Chicago

$1,198,000

3762 S Indiana Avenue, Chicago

9 Beds 0 Baths 0 SqFt Residential Income MLS® # 12706029

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New
5338 W Montrose Avenue, Chicago

$1,195,000

5338 W Montrose Avenue, Chicago

9 Beds 0 Baths 0 SqFt Residential Income MLS® # 12775394

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60 E Monroe Street 4002, Chicago

$1,195,000

60 E Monroe Street 4002, Chicago

3 Beds 2 Baths 2,141 SqFt Residential MLS® # 12765843

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New Open House
1000 W Washington Boulevard 517, Chicago

$1,195,000

1000 W Washington Boulevard 517, Chicago

3 Beds 3 Baths 2,500 SqFt Residential
Sat, Oct 10th, 2026 @ 1pm - 3pm
MLS® # 12761541

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New
4913 N Damen Avenue 3, Chicago

$1,195,000

4913 N Damen Avenue 3, Chicago

3 Beds 2.5 Baths 2,100 SqFt Residential MLS® # 12754633

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4724 N Sacramento Avenue, Chicago

$1,195,000

4724 N Sacramento Avenue, Chicago

9 Beds 0 Baths 0 SqFt Residential Income MLS® # 12752430

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New
25 E Superior Street 3701, Chicago

$1,195,000

25 E Superior Street 3701, Chicago

3 Beds 3 Baths 2,650 SqFt Residential MLS® # 12725530

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Posted by Leo Clark. on

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