Chicago Real Estate News & Neighborhood Notes

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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• Over $1,000,000

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$1,900,000

1629 N Burling Street 3, Chicago

4 Beds 3.5 Baths 2,579 SqFt Residential MLS® # 12753736

New

$1,900,000

2026 N Orleans Street 1n, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12751795

$1,900,000

2235 W Oakdale Avenue 20-b, Chicago

5 Beds 3.5 Baths 3,885 SqFt Residential MLS® # 12628802

New

$1,899,000

800 N Michigan Avenue 5501, Chicago

3 Beds 3.5 Baths 4,200 SqFt Residential MLS® # 12772697

$1,897,747

180 E Pearson Street 3707, Chicago

3 Beds 3.5 Baths 2,754 SqFt Residential MLS® # 12686123

New

$1,895,000

180 E Pearson Street 6401, Chicago

3 Beds 3 Baths 2,754 SqFt Residential MLS® # 12774071

Open House

$1,895,000

2071 N Oakley Avenue, Chicago

4 Beds 3.5 Baths 0 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 12pm - 2pm

MLS® # 12770642

New

$1,895,000

1716 W Berwyn Avenue, Chicago

3 Beds 4.5 Baths 3,843 SqFt Residential MLS® # 12762354

$1,895,000

60 E Monroe Street 6102, Chicago

3 Beds 3 Baths 3,300 SqFt Residential MLS® # 12745267

$1,895,000

1844 W Barry Avenue, Chicago

4 Beds 3.5 Baths 3,689 SqFt Residential MLS® # 12728692

$1,895,000

443 W Aldine Street 3, Chicago

5 Beds 3 Baths 3,500 SqFt Residential MLS® # 12728602

$1,890,000

1529 W Adams Street, Chicago

4 Beds 4.5 Baths 4,950 SqFt Residential MLS® # 12740940

New Open House

$1,850,000

2029 W George Street, Chicago

4 Beds 3.5 Baths 4,689 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 11am - 1pm

MLS® # 12771301

$1,850,000

159 E Walton Place 8d, Chicago

3 Beds 3.5 Baths 3,157 SqFt Residential MLS® # 12719761

New

$1,849,000

2026 N Orleans Street 1s, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12771434

$1,849,000

3841 N Kenneth Avenue, Chicago

5 Beds 4.5 Baths 3,950 SqFt Residential MLS® # 12743447

$1,824,999

↓ $24,001

229 E Lake Shore Drive 10e, Chicago

4 Beds 4 Baths 3,735 SqFt Residential MLS® # 12566727

$1,800,000

2927 N Oakley Avenue, Chicago

4 Beds 4.5 Baths 3,197 SqFt Residential MLS® # 12755346

New

$1,800,000

111 E Chestnut Street 56ab, Chicago

2 Beds 2.5 Baths 2,600 SqFt Residential MLS® # 12754110

$1,800,000

111 S Peoria Street 313, Chicago

4 Beds 4.5 Baths 0 SqFt Residential MLS® # 12743577

$1,800,000

159 E Walton Place 7d, Chicago

3 Beds 3.5 Baths 3,157 SqFt Residential MLS® # 12723886

$1,800,000

175 E Delaware Place 7201-7202, Chicago

3 Beds 3 Baths 3,050 SqFt Residential MLS® # 12697463

$1,799,000

339 W Webster Avenue 1a, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12765810

New

$1,799,000

2135 W Montrose Avenue, Chicago

4 Beds 3.5 Baths 4,500 SqFt Residential MLS® # 12751655

New

$1,797,000

180 E Pearson Street 3807, Chicago

3 Beds 3 Baths 2,754 SqFt Residential MLS® # 12781063

New

$1,795,000

1310 W Roscoe Street, Chicago

6 Beds 4.5 Baths 4,000 SqFt Residential MLS® # 12777941

New Open House

$1,795,000

2520 W Shakespeare Avenue, Chicago

3 Beds 3.5 Baths 3,600 SqFt Residential

Open House

Sun, Oct 11th, 2026 @ 2pm - 4pm

MLS® # 12772230

$1,795,000

↓ $80,000

435 N Michigan Avenue 408, Chicago

2 Beds 2.5 Baths 1,949 SqFt Residential MLS® # 12750924

$1,789,000

↓ $40,000

450 E Waterside Drive 3409, Chicago

2 Beds 3 Baths 2,714 SqFt Residential MLS® # 12690367

New

$1,780,000

1415 W Augusta Boulevard, Chicago

9 Beds 0 Baths 0 SqFt Residential Income MLS® # 12755194

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• Luxury Chicago Real Estate (36)
• Luxury Chicago Condos (14)