$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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3726 N Ashland Avenue Ph, Chicago

$1,499,000

3726 N Ashland Avenue Ph, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12752459

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910 W Madison Street 904e, Chicago

$1,499,000

910 W Madison Street 904e, Chicago

3 Beds 3 Baths 2,500 SqFt Residential MLS® # 12745354

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3405 N Seminary Avenue, Chicago

$1,499,000

3405 N Seminary Avenue, Chicago

6 Beds 0 Baths 0 SqFt Residential Income MLS® # 12739752

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505 N Lake Shore Drive 4901-12, Chicago

$1,499,000

505 N Lake Shore Drive 4901-12, Chicago

3 Beds 3.5 Baths 3,000 SqFt Residential MLS® # 12737459

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Open House
3700 N Lake Shore Drive 104, Chicago

$1,495,000

3700 N Lake Shore Drive 104, Chicago

4 Beds 3 Baths 3,001 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 1pm
MLS® # 12769204

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New
1319 N Sandburg Terrace, Chicago

$1,495,000

1319 N Sandburg Terrace, Chicago

4 Beds 4 Baths 2,850 SqFt Residential MLS® # 12762102

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401 N Wabash Avenue 74f, Chicago

$1,495,000

↓ $105,000

401 N Wabash Avenue 74f, Chicago

2 Beds 2.5 Baths 1,952 SqFt Residential MLS® # 12618985

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1725 N Troy Street, Chicago

$1,490,000

↓ $70,000

1725 N Troy Street, Chicago

5 Beds 5.5 Baths 6,400 SqFt Residential MLS® # 12694881

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1347 W Granville Avenue, Chicago

$1,485,000

1347 W Granville Avenue, Chicago

10 Beds 0 Baths 0 SqFt Residential Income MLS® # 12748491

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10 E Ontario Street 5001-02, Chicago

$1,475,000

10 E Ontario Street 5001-02, Chicago

3 Beds 3 Baths 2,400 SqFt Residential MLS® # 12754794

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2040 N Damen Avenue 2, Chicago

$1,475,000

2040 N Damen Avenue 2, Chicago

3 Beds 2.5 Baths 2,900 SqFt Residential MLS® # 12743406

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1260 N Astor Street 7, Chicago

$1,475,000

1260 N Astor Street 7, Chicago

5 Beds 5 Baths 4,500 SqFt Residential MLS® # 12743102

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Open House
6144 N Nickerson Avenue, Chicago

$1,475,000

6144 N Nickerson Avenue, Chicago

6 Beds 3.5 Baths 4,219 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 2pm
MLS® # 12735782

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3739 N Clifton Avenue 1, Chicago

$1,465,000

↓ $35,000

3739 N Clifton Avenue 1, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12703271

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New
1346 W Addison Street 3e, Chicago

$1,450,000

1346 W Addison Street 3e, Chicago

3 Beds 3.5 Baths 2,800 SqFt Residential MLS® # 12772580

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New
600 N Lake Shore Drive 1011, Chicago

$1,450,000

600 N Lake Shore Drive 1011, Chicago

3 Beds 3 Baths 2,124 SqFt Residential MLS® # 12770732

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Open House
3921 N Greenview Avenue 1, Chicago

$1,450,000

3921 N Greenview Avenue 1, Chicago

5 Beds 3 Baths 3,409 SqFt Residential
Sun, Oct 11th, 2026 @ 1pm - 2:30pm
MLS® # 12767401

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New
1839 N Dayton Street 204, Chicago

$1,450,000

1839 N Dayton Street 204, Chicago

3 Beds 2 Baths 0 SqFt Residential MLS® # 12766833

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New
3721 N Kenmore Avenue 1, Chicago

$1,450,000

3721 N Kenmore Avenue 1, Chicago

3 Beds 3.5 Baths 0 SqFt Residential MLS® # 12764345

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2237 W Lyndale Street, Chicago

$1,450,000

2237 W Lyndale Street, Chicago

4 Beds 3.5 Baths 2,257 SqFt Residential MLS® # 12760956

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2908 N Burling Street 1, Chicago

$1,450,000

2908 N Burling Street 1, Chicago

4 Beds 2.5 Baths 3,400 SqFt Residential MLS® # 12755796

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1856 W Superior Street, Chicago

$1,450,000

1856 W Superior Street, Chicago

5 Beds 4.5 Baths 3,750 SqFt Residential MLS® # 12753041

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1901 W Berwyn Avenue, Chicago

$1,450,000

1901 W Berwyn Avenue, Chicago

6 Beds 0 Baths 0 SqFt Residential Income MLS® # 12748897

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344 W Scott Street, Chicago

$1,450,000

344 W Scott Street, Chicago

3 Beds 3.5 Baths 3,300 SqFt Residential MLS® # 12713927

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1808 W Armitage Street, Chicago

$1,450,000

1808 W Armitage Street, Chicago

7 Beds 0 Baths 0 SqFt Residential Income MLS® # 12705248

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815 N Milwaukee Avenue, Chicago

$1,450,000

815 N Milwaukee Avenue, Chicago

4 Beds 2.5 Baths 3,208 SqFt Residential MLS® # 12704009

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914 W Fletcher Street 1, Chicago

$1,450,000

914 W Fletcher Street 1, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12681838

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New
1919 S Prairie Avenue 3, Chicago

$1,449,000

1919 S Prairie Avenue 3, Chicago

3 Beds 2.5 Baths 3,700 SqFt Residential MLS® # 12766311

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New
600 N Lake Shore Drive 2411, Chicago

$1,449,000

600 N Lake Shore Drive 2411, Chicago

3 Beds 3 Baths 2,124 SqFt Residential MLS® # 12763928

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1454 N Wieland Street, Chicago

$1,445,500

↓ $49,500

1454 N Wieland Street, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12741980

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Posted by Leo Clark. on

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