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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$3,299,990

2714 N Magnolia Avenue, Chicago

6 Beds 4.5 Baths 4,000 SqFt Residential MLS® # 12757125

New

$3,299,000

14 N Peoria Street 6h-7h, Chicago

4 Beds 4 Baths 5,100 SqFt Residential MLS® # 12679827

New

$3,250,000

800 N Michigan Avenue 4801, Chicago

3 Beds 2.5 Baths 4,200 SqFt Residential MLS® # 12634613

$3,249,000

2054 W Grand Avenue, Chicago

2 Beds 0 Baths 0 SqFt Residential Income MLS® # 12652644

$3,200,000

55 E Erie Street 5302, Chicago

3 Beds 3.5 Baths 4,200 SqFt Residential MLS® # 12755318

$3,200,000

1718 W Wrightwood Avenue, Chicago

4 Beds 5.5 Baths 8,000 SqFt Residential MLS® # 12724794

$3,195,000

132 E Delaware Place 6206, Chicago

3 Beds 3 Baths 2,750 SqFt Residential MLS® # 12745959

Open House

$3,175,000

435 N Michigan Avenue 1801, Chicago

3 Beds 3.5 Baths 3,374 SqFt Residential

Open House

Sun, Oct 25th, 2026 @ 12:30pm - 2:30pm

MLS® # 12192315

$3,025,000

21 N May Street 501, Chicago

3 Beds 3.5 Baths 3,557 SqFt Residential MLS® # 12646444

$3,000,000

180 E Pearson Street 5601, Chicago

3 Beds 3 Baths 3,300 SqFt Residential MLS® # 12709944

$3,000,000

1282 W Washington Boulevard Phb, Chicago

4 Beds 3.5 Baths 3,362 SqFt Residential MLS® # 12705933

$3,000,000

1282 W Washington Boulevard 2a, Chicago

5 Beds 4.5 Baths 3,433 SqFt Residential MLS® # 12615483

$3,000,000

415 E North Water Street 3205, Chicago

3 Beds 4 Baths 9,279 SqFt Residential MLS® # 12341284

$2,999,900

1211 S Prairie Avenue 5400, Chicago

4 Beds 4.5 Baths 9,542 SqFt Residential MLS® # 12759371

$2,995,000

840 N Lake Shore Drive 1801, Chicago

3 Beds 3.5 Baths 4,308 SqFt Residential MLS® # 12721318

$2,995,000

435 N Michigan Avenue 1803, Chicago

3 Beds 3.5 Baths 3,390 SqFt Residential MLS® # 12600975

$2,995,000

123 S Peoria Street P2, Chicago

5 Beds 5.5 Baths 3,859 SqFt Residential MLS® # 12540913

$2,995,000

416 W Deming Place 4, Chicago

3 Beds 3.5 Baths 3,430 SqFt Residential MLS® # 12313746

$2,990,000

2347 N Geneva Terrace, Chicago

5 Beds 3.5 Baths 4,500 SqFt Residential MLS® # 12724964

New

$2,950,000

460 W Superior Street 4-5, Chicago

3 Beds 4.5 Baths 6,400 SqFt Residential MLS® # 12766498

$2,950,000

211 N Harbor Drive 4301, Chicago

4 Beds 3.5 Baths 3,013 SqFt Residential MLS® # 12548620

$2,900,000

435 N Michigan Avenue 401, Chicago

3 Beds 3.5 Baths 2,900 SqFt Residential MLS® # 12742789

$2,900,000

65 E Goethe Street 3w, Chicago

3 Beds 3.5 Baths 4,390 SqFt Residential MLS® # 12651986

$2,900,000

363 E Wacker Drive 3608, Chicago

3 Beds 2.5 Baths 2,826 SqFt Residential MLS® # 12638404

New

$2,899,500

111 W Maple Street 3402-3404, Chicago

2 Beds 3.5 Baths 2,500 SqFt Residential MLS® # 12780897

New

$2,899,000

1834 N Hudson Avenue 2, Chicago

5 Beds 5 Baths 0 SqFt Residential MLS® # 12759621

$2,897,747

180 E Pearson Street 7203, Chicago

4 Beds 3.5 Baths 3,320 SqFt Residential MLS® # 12701195

$2,875,000

1816 N Hudson Avenue, Chicago

5 Beds 4.5 Baths 0 SqFt Residential MLS® # 12354016

New

$2,850,000

800 N Michigan Avenue 4201, Chicago

3 Beds 2.5 Baths 4,200 SqFt Residential MLS® # 12777451

$2,850,000

6 N Carpenter Street 5b, Chicago

5 Beds 4.5 Baths 3,767 SqFt Residential MLS® # 12753243

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