$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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4616 N Claremont Avenue, Chicago

$2,199,000

4616 N Claremont Avenue, Chicago

6 Beds 5 Baths 4,200 SqFt Residential MLS® # 12690843

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211 N Harbor Drive Th01, Chicago

$2,199,000

211 N Harbor Drive Th01, Chicago

3 Beds 2.5 Baths 3,134 SqFt Residential MLS® # 12667572

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2057 N Oakley Avenue, Chicago

$2,195,000

2057 N Oakley Avenue, Chicago

4 Beds 3.5 Baths 3,260 SqFt Residential MLS® # 12760262

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2330 N Kedzie Boulevard, Chicago

$2,195,000

2330 N Kedzie Boulevard, Chicago

5 Beds 4 Baths 6,178 SqFt Residential MLS® # 12729706

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New
4923 S Greenwood Avenue, Chicago

$2,175,000

4923 S Greenwood Avenue, Chicago

8 Beds 4.5 Baths 5,000 SqFt Residential MLS® # 12752094

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2150 W Monroe Street, Chicago

$2,165,000

2150 W Monroe Street, Chicago

6 Beds 4.5 Baths 3,586 SqFt Residential MLS® # 12555696

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New
1811 W Superior Street, Chicago

$2,150,000

1811 W Superior Street, Chicago

6 Beds 5 Baths 4,200 SqFt Residential MLS® # 12755419

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2041 W Roscoe Street Ph, Chicago

$2,150,000

2041 W Roscoe Street Ph, Chicago

4 Beds 2.5 Baths 4,330 SqFt Residential MLS® # 12748181

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1942 N Orchard Street 1n, Chicago

$2,150,000

1942 N Orchard Street 1n, Chicago

3 Beds 3.5 Baths 0 SqFt Residential MLS® # 12723739

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Open House
2333 N Cambridge Avenue F, Chicago

$2,150,000

2333 N Cambridge Avenue F, Chicago

4 Beds 3.5 Baths 2,930 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 12:30pm
MLS® # 12723683

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New Open House
2333 N Cambridge Avenue E, Chicago

$2,100,000

2333 N Cambridge Avenue E, Chicago

4 Beds 3.5 Baths 2,930 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 12:30pm
MLS® # 12771590

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New Open House
2329 N Cambridge Avenue C, Chicago

$2,100,000

2329 N Cambridge Avenue C, Chicago

4 Beds 3.5 Baths 2,930 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 12:30pm
MLS® # 12771584

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New Open House
401 N Aberdeen Street 4n, Chicago

$2,100,000

401 N Aberdeen Street 4n, Chicago

3 Beds 3 Baths 3,100 SqFt Residential
Sat, Oct 10th, 2026 @ 12am - 1:30pm
MLS® # 12767483

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New
707 W Gordon Terrace, Chicago

$2,100,000

707 W Gordon Terrace, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12759815

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New Open House
2679 N Orchard Street 1n, Chicago

$2,100,000

2679 N Orchard Street 1n, Chicago

4 Beds 3.5 Baths 0 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 2pm
MLS® # 12753073

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New
2679 N Orchard Street 1s, Chicago

$2,100,000

2679 N Orchard Street 1s, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12753071

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2109 W Sunnyside Avenue, Chicago

$2,100,000

2109 W Sunnyside Avenue, Chicago

5 Beds 5 Baths 3,800 SqFt Residential MLS® # 12720002

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461 W Melrose Street, Chicago

$2,100,000

↓ $140,000

461 W Melrose Street, Chicago

6 Beds 4 Baths 5,246 SqFt Residential MLS® # 12594841

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3617 N Magnolia Avenue 2, Chicago

$2,100,000

3617 N Magnolia Avenue 2, Chicago

4 Beds 4.5 Baths 0 SqFt Residential MLS® # 12566596

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4100 N Oakley Avenue, Chicago

$2,099,988

4100 N Oakley Avenue, Chicago

5 Beds 5 Baths 4,000 SqFt Residential MLS® # 12753914

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New
1728 N Hudson Avenue, Chicago

$2,099,000

1728 N Hudson Avenue, Chicago

4 Beds 4.5 Baths 4,000 SqFt Residential MLS® # 12775199

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New Open House
1625 W Julian Street, Chicago

$2,099,000

1625 W Julian Street, Chicago

3 Beds 4 Baths 3,851 SqFt Residential
Sun, Oct 11th, 2026 @ 12pm - 2pm
MLS® # 12774089

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New
2323 N Lister Avenue, Chicago

$2,099,000

2323 N Lister Avenue, Chicago

11 Beds 0 Baths 0 SqFt Residential Income MLS® # 12766430

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New
2063 N Humboldt Boulevard, Chicago

$2,099,000

2063 N Humboldt Boulevard, Chicago

6 Beds 5 Baths 4,215 SqFt Residential MLS® # 12766322

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2243 N Halsted Street 3s, Chicago

$2,095,000

2243 N Halsted Street 3s, Chicago

4 Beds 2.5 Baths 0 SqFt Residential MLS® # 12755096

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New
2254 N Fremont Street, Chicago

$2,095,000

2254 N Fremont Street, Chicago

6 Beds 4 Baths 3,822 SqFt Residential MLS® # 12385258

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New
1728 N Sawyer Avenue, Chicago

$2,094,000

1728 N Sawyer Avenue, Chicago

10 Beds 0 Baths 0 SqFt Residential Income MLS® # 12763697

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401 N Wabash Avenue 86b, Chicago

$2,050,000

↓ $50,000

401 N Wabash Avenue 86b, Chicago

2 Beds 3 Baths 2,400 SqFt Residential MLS® # 12645566

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1839 N Dayton Street 101, Chicago

$2,000,000

1839 N Dayton Street 101, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12766840

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2426 N Burling Street, Chicago

$2,000,000

2426 N Burling Street, Chicago

3 Beds 3.5 Baths 3,000 SqFt Residential MLS® # 12758898

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Posted by Leo Clark. on

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