$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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3126 W Lyndale Street 2, Chicago

$1,099,000

3126 W Lyndale Street 2, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12666661

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225 N Columbus Drive 7201, Chicago

$1,099,000

↓ $26,000

225 N Columbus Drive 7201, Chicago

3 Beds 2.5 Baths 1,800 SqFt Residential MLS® # 12592409

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6106 N Hermitage Avenue, Chicago

$1,099,000

↓ $50,000

6106 N Hermitage Avenue, Chicago

2 Beds 3.5 Baths 3,300 SqFt Residential MLS® # 12532260

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3100 N Kenmore Avenue 3j, Chicago

$1,095,000

3100 N Kenmore Avenue 3j, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12765905

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1728 N Sawyer Avenue Rear, Chicago

$1,095,000

1728 N Sawyer Avenue Rear, Chicago

5 Beds 3.5 Baths 3,100 SqFt Residential MLS® # 12703999

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New
211 N Harbor Drive 3206, Chicago

$1,090,000

211 N Harbor Drive 3206, Chicago

2 Beds 2.5 Baths 1,384 SqFt Residential MLS® # 12780484

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211 N Harbor Drive 3209, Chicago

$1,090,000

211 N Harbor Drive 3209, Chicago

3 Beds 2 Baths 1,550 SqFt Residential MLS® # 12713659

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3547 N Reta Avenue 101, Chicago

$1,090,000

↓ $60,000

3547 N Reta Avenue 101, Chicago

4 Beds 2.5 Baths 2,800 SqFt Residential MLS® # 12712780

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1201 S Prairie Avenue 3303, Chicago

$1,090,000

1201 S Prairie Avenue 3303, Chicago

3 Beds 2 Baths 1,746 SqFt Residential MLS® # 12625837

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4945 W Berenice Avenue, Chicago

$1,085,000

↓ $15,000

4945 W Berenice Avenue, Chicago

5 Beds 3.5 Baths 3,099 SqFt Residential MLS® # 12751215

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211 N Harbor Drive 3009, Chicago

$1,080,000

211 N Harbor Drive 3009, Chicago

3 Beds 2 Baths 1,550 SqFt Residential MLS® # 12768188

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211 N Harbor Drive 3006, Chicago

$1,080,000

211 N Harbor Drive 3006, Chicago

2 Beds 2.5 Baths 1,384 SqFt Residential MLS® # 12735043

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New
5948 W Grace Street, Chicago

$1,079,800

5948 W Grace Street, Chicago

4 Beds 4.5 Baths 3,606 SqFt Residential MLS® # 12759188

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New
2014 N Whipple Street, Chicago

$1,079,000

2014 N Whipple Street, Chicago

7 Beds 0 Baths 0 SqFt Residential Income MLS® # 12767384

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New
1648 W Division Street 707, Chicago

$1,075,000

1648 W Division Street 707, Chicago

3 Beds 2.5 Baths 1,915 SqFt Residential MLS® # 12718681

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1120 N Lake Shore Drive 16b, Chicago

$1,075,000

↓ $100,000

1120 N Lake Shore Drive 16b, Chicago

3 Beds 3.5 Baths 0 SqFt Residential MLS® # 12716342

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New
3258 N Ridgeway Avenue, Chicago

$1,075,000

3258 N Ridgeway Avenue, Chicago

8 Beds 0 Baths 0 SqFt Residential Income MLS® # 12652801

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234 W Polk Street 3704, Chicago

$1,075,000

234 W Polk Street 3704, Chicago

2 Beds 2 Baths 1,535 SqFt Residential MLS® # 12538230

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401 N Wabash Avenue 37c, Chicago

$1,075,000

401 N Wabash Avenue 37c, Chicago

2 Beds 2.5 Baths 1,800 SqFt Residential MLS® # 12305200

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340 E Randolph Street 4802, Chicago

$1,074,999

↓ $24,001

340 E Randolph Street 4802, Chicago

2 Beds 2.5 Baths 1,647 SqFt Residential MLS® # 12725282

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1346 N Kedzie Avenue, Chicago

$1,074,000

1346 N Kedzie Avenue, Chicago

9 Beds 0 Baths 0 SqFt Residential Income MLS® # 12751936

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3739 N Clifton Avenue 3, Chicago

$1,065,000

↓ $35,000

3739 N Clifton Avenue 3, Chicago

2 Beds 2 Baths 0 SqFt Residential MLS® # 12703662

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2333 W Ohio Street, Chicago

$1,055,000

↓ $44,000

2333 W Ohio Street, Chicago

6 Beds 0 Baths 0 SqFt Residential Income MLS® # 12756776

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211 N Harbor Drive 2509, Chicago

$1,055,000

211 N Harbor Drive 2509, Chicago

3 Beds 2 Baths 1,550 SqFt Residential MLS® # 12744216

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New Open House
1938 N Sawyer Avenue 1, Chicago

$1,050,000

1938 N Sawyer Avenue 1, Chicago

4 Beds 3.5 Baths 3,200 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 12:30pm
MLS® # 12780386

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New Open House
2032 N Burling Street 3, Chicago

$1,050,000

2032 N Burling Street 3, Chicago

3 Beds 3 Baths 0 SqFt Residential
Sun, Oct 11th, 2026 @ 2pm - 3:30pm
MLS® # 12779960

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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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Posted by Leo Clark. on

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