$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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2332 N Maplewood Avenue, Chicago

$1,699,000

2332 N Maplewood Avenue, Chicago

6 Beds 3.5 Baths 0 SqFt Residential MLS® # 12771997

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1340 W Chestnut Street 401, Chicago

$1,699,000

↓ $76,000

1340 W Chestnut Street 401, Chicago

5 Beds 4.5 Baths 4,200 SqFt Residential MLS® # 12756258

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New
2448 W Moffat Street, Chicago

$1,699,000

2448 W Moffat Street, Chicago

3 Beds 4.5 Baths 3,317 SqFt Residential MLS® # 12725030

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60 E Monroe Street 5601, Chicago

$1,698,000

60 E Monroe Street 5601, Chicago

3 Beds 3 Baths 2,450 SqFt Residential MLS® # 12740413

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New
505 N Lake Shore Drive 6801, Chicago

$1,695,000

505 N Lake Shore Drive 6801, Chicago

3 Beds 3 Baths 3,000 SqFt Residential MLS® # 12766791

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2657 W Belden Avenue, Chicago

$1,695,000

↓ $100,000

2657 W Belden Avenue, Chicago

5 Beds 3.5 Baths 3,800 SqFt Residential MLS® # 12753514

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Open House
4942 S Ellis Avenue, Chicago

$1,695,000

4942 S Ellis Avenue, Chicago

6 Beds 5 Baths 6,144 SqFt Residential
Sat, Oct 10th, 2026 @ 1pm - 2:30pm
MLS® # 12705893

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10 E Delaware Place 29e, Chicago

$1,690,000

↓ $110,000

10 E Delaware Place 29e, Chicago

3 Beds 3.5 Baths 2,161 SqFt Residential MLS® # 12721327

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New
401 N Wabash Avenue 30j, Chicago

$1,675,000

401 N Wabash Avenue 30j, Chicago

2 Beds 2.5 Baths 2,076 SqFt Residential MLS® # 12753886

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2333 N Cambridge Avenue B, Chicago

$1,675,000

2333 N Cambridge Avenue B, Chicago

3 Beds 3 Baths 2,390 SqFt Residential MLS® # 12723623

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1743 W Newport Avenue, Chicago

$1,675,000

1743 W Newport Avenue, Chicago

4 Beds 5 Baths 4,200 SqFt Residential MLS® # 12269352

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2215 W Roscoe Street, Chicago

$1,670,000

↓ $9,000

2215 W Roscoe Street, Chicago

4 Beds 3.5 Baths 2,800 SqFt Residential MLS® # 12731614

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New Open House
500 W Superior Street 2401, Chicago

$1,650,000

500 W Superior Street 2401, Chicago

3 Beds 2.5 Baths 3,550 SqFt Residential
Sun, Oct 11th, 2026 @ 12pm - 1:30pm
MLS® # 12769705

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New
828 W Lill Avenue, Chicago

$1,650,000

828 W Lill Avenue, Chicago

7 Beds 0 Baths 0 SqFt Residential Income MLS® # 12758878

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1000 W Washington Boulevard 538-539, Chicago

$1,650,000

1000 W Washington Boulevard 538-539, Chicago

4 Beds 4 Baths 3,300 SqFt Residential MLS® # 12750912

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New
1420 N Elk Grove Avenue 1, Chicago

$1,650,000

1420 N Elk Grove Avenue 1, Chicago

4 Beds 3.5 Baths 3,200 SqFt Residential MLS® # 12735488

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403 N Wabash Avenue 10b, Chicago

$1,650,000

403 N Wabash Avenue 10b, Chicago

3 Beds 3.5 Baths 2,517 SqFt Residential MLS® # 12716731

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914 W Fletcher Street Ph, Chicago

$1,650,000

914 W Fletcher Street Ph, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12681915

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3136 W Logan Boulevard, Chicago

$1,650,000

↓ $50,000

3136 W Logan Boulevard, Chicago

13 Beds 0 Baths 0 SqFt Residential Income MLS® # 12652469

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5844 N Navarre Avenue, Chicago

$1,649,000

5844 N Navarre Avenue, Chicago

4 Beds 4.5 Baths 4,992 SqFt Residential MLS® # 12762414

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310 S Michigan Avenue 1100, Chicago

$1,649,000

310 S Michigan Avenue 1100, Chicago

4 Beds 4 Baths 3,350 SqFt Residential MLS® # 12740439

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363 E Wacker Drive 3404, Chicago

$1,635,000

363 E Wacker Drive 3404, Chicago

2 Beds 2 Baths 1,711 SqFt Residential MLS® # 12728755

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New
3508 W Belden Avenue, Chicago

$1,630,000

3508 W Belden Avenue, Chicago

3 Beds 3.5 Baths 3,800 SqFt Residential MLS® # 12763307

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New
1325 N Astor Street 2, Chicago

$1,600,000

1325 N Astor Street 2, Chicago

3 Beds 4 Baths 4,300 SqFt Residential MLS® # 12772455

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2929 N Oakley Avenue 46-j, Chicago

$1,600,000

2929 N Oakley Avenue 46-j, Chicago

4 Beds 3.5 Baths 3,724 SqFt Residential MLS® # 12768582

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New
2205 N Talman Avenue, Chicago

$1,600,000

2205 N Talman Avenue, Chicago

4 Beds 3.5 Baths 2,866 SqFt Residential MLS® # 12767085

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New
1824 W Superior Street, Chicago

$1,599,900

1824 W Superior Street, Chicago

4 Beds 3.5 Baths 4,000 SqFt Residential MLS® # 12755189

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60 E Monroe Street 5301, Chicago

$1,599,900

↓ $95,100

60 E Monroe Street 5301, Chicago

3 Beds 3 Baths 2,450 SqFt Residential MLS® # 12572008

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New Open House
1000 W Washington Boulevard 202, Chicago

$1,599,000

1000 W Washington Boulevard 202, Chicago

4 Beds 4 Baths 3,036 SqFt Residential
Sat, Oct 10th, 2026 @ 1pm - 2:30pm
MLS® # 12778133

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403 N Wabash Street 15b, Chicago

$1,599,000

403 N Wabash Street 15b, Chicago

3 Beds 3.5 Baths 2,517 SqFt Residential MLS® # 12758679

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Posted by Leo Clark. on

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