$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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331 W Evergreen Avenue, Chicago

$1,435,000

↓ $64,000

331 W Evergreen Avenue, Chicago

4 Beds 3.5 Baths 3,100 SqFt Residential MLS® # 12753212

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3823 N Alta Vista Terrace, Chicago

$1,430,000

3823 N Alta Vista Terrace, Chicago

4 Beds 3 Baths 0 SqFt Residential MLS® # 12741737

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New
920 W Monroe Street 501, Chicago

$1,425,000

920 W Monroe Street 501, Chicago

2 Beds 2 Baths 1,428 SqFt Residential MLS® # 12777258

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New
1418 N Lake Shore Drive 28, Chicago

$1,400,000

1418 N Lake Shore Drive 28, Chicago

2 Beds 2.5 Baths 3,100 SqFt Residential MLS® # 12760630

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420 W Grand Avenue 5d, Chicago

$1,400,000

420 W Grand Avenue 5d, Chicago

2 Beds 2 Baths 2,500 SqFt Residential MLS® # 12700146

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New
4024 N California Avenue, Chicago

$1,399,900

4024 N California Avenue, Chicago

5 Beds 3.5 Baths 4,500 SqFt Residential MLS® # 12778602

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New Open House
2541 N Wayne Avenue 1n, Chicago

$1,399,900

2541 N Wayne Avenue 1n, Chicago

4 Beds 3.5 Baths 0 SqFt Residential
Sat, Oct 10th, 2026 @ 10am - 12pm
MLS® # 12778351

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New Open House
1951 W Dickens Avenue 1, Chicago

$1,399,000

1951 W Dickens Avenue 1, Chicago

3 Beds 2.5 Baths 0 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 12:30pm
MLS® # 12761588

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New
1327 W Walton Street, Chicago

$1,399,000

1327 W Walton Street, Chicago

7 Beds 0 Baths 0 SqFt Residential Income MLS® # 12740764

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1721 W Julian Street, Chicago

$1,399,000

1721 W Julian Street, Chicago

8 Beds 0 Baths 0 SqFt Residential Income MLS® # 12711707

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New
1826 W Farragut Avenue, Chicago

$1,399,000

1826 W Farragut Avenue, Chicago

4 Beds 3 Baths 2,400 SqFt Residential MLS® # 12670789

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481 N Clinton Street, Chicago

$1,399,000

↓ $51,000

481 N Clinton Street, Chicago

5 Beds 3.5 Baths 3,447 SqFt Residential MLS® # 12567829

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2743 N Greenview Avenue 1, Chicago

$1,395,000

2743 N Greenview Avenue 1, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12767404

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New
2314 N Lincoln Park West 11s, Chicago

$1,395,000

2314 N Lincoln Park West 11s, Chicago

3 Beds 3 Baths 0 SqFt Residential MLS® # 12758736

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57 E Delaware Place 3804, Chicago

$1,395,000

↓ $100,000

57 E Delaware Place 3804, Chicago

2 Beds 2.5 Baths 3,050 SqFt Residential MLS® # 12639998

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4020 N Francisco Avenue, Chicago

$1,395,000

4020 N Francisco Avenue, Chicago

3 Beds 3.5 Baths 4,000 SqFt Residential MLS® # 12618606

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310 S Michigan Avenue 1500, Chicago

$1,395,000

↓ $100,000

310 S Michigan Avenue 1500, Chicago

5 Beds 5 Baths 3,400 SqFt Residential MLS® # 12544545

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401 N Wabash Avenue 37k, Chicago

$1,390,000

↓ $110,000

401 N Wabash Avenue 37k, Chicago

2 Beds 2.5 Baths 2,063 SqFt Residential MLS® # 12594795

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New
211 N Harbor Drive 2808, Chicago

$1,385,000

211 N Harbor Drive 2808, Chicago

3 Beds 2.5 Baths 1,574 SqFt Residential MLS® # 12737705

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600 N Lake Shore Drive 2011, Chicago

$1,380,000

600 N Lake Shore Drive 2011, Chicago

3 Beds 3 Baths 2,124 SqFt Residential MLS® # 12765205

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2042 N Racine Avenue 101, Chicago

$1,380,000

↓ $39,000

2042 N Racine Avenue 101, Chicago

4 Beds 2.5 Baths 2,322 SqFt Residential MLS® # 12738892

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New
2745 N Greenview Avenue 1, Chicago

$1,375,000

2745 N Greenview Avenue 1, Chicago

4 Beds 3.5 Baths 2,750 SqFt Residential MLS® # 12777459

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New
900 W Washington Boulevard 504, Chicago

$1,375,000

900 W Washington Boulevard 504, Chicago

2 Beds 2.5 Baths 1,605 SqFt Residential MLS® # 12777400

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1400 W Monroe Street 5b, Chicago

$1,375,000

1400 W Monroe Street 5b, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12756966

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3045 W Ardmore Avenue, Chicago

$1,375,000

3045 W Ardmore Avenue, Chicago

5 Beds 3.5 Baths 3,500 SqFt Residential MLS® # 12742597

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1803 W Armitage Avenue 2, Chicago

$1,375,000

1803 W Armitage Avenue 2, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12730158

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4109 N Lawndale Avenue, Chicago

$1,375,000

↓ $50,000

4109 N Lawndale Avenue, Chicago

3 Beds 3.5 Baths 3,800 SqFt Residential MLS® # 12719274

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3820 N Damen Avenue 1, Chicago

$1,370,000

3820 N Damen Avenue 1, Chicago

4 Beds 3.5 Baths 2,800 SqFt Residential MLS® # 12769330

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New
211 N Harbor Drive 3208, Chicago

$1,370,000

211 N Harbor Drive 3208, Chicago

3 Beds 2.5 Baths 1,574 SqFt Residential MLS® # 12713650

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New
1461 W Winona Street, Chicago

$1,350,000

1461 W Winona Street, Chicago

6 Beds 0 Baths 0 SqFt Residential Income MLS® # 12774861

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Posted by Leo Clark. on

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