Most Expensive Homes in Chicago IL

Interested in Chicago's most expensive homes for sale? If a luxury condo isn't your thing, you've probably noticed quite a few amazing single-family homes listed on the market at any given time. Neighborhoods like Lakeview, Roscoe Village, and Lincoln Park are where you'll find some of the city's largest and most expensive homes, but multi-million dollar homes and estates can also be found all over the city, as you'll see below. 

If you would like more information on any of the most expensive homes for sale in Chicago, our team can provide with with additional details, up-to-the-minute market data, disclosures associated with a property, and also a list of recently sold luxury homes to help you better determine an appropriate offer. And as always, we also encourage all luxury home buyers in Chicago to register for a free account, allowing you to stay one-step ahead of other home buyers considering a luxury home in the Chicago area. 

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New
353 W Belden Avenue, Chicago, 60614

$3,650,000

353 W Belden Avenue, Chicago, 60614

6 Beds 6.5 Baths 5,000 SqFt Residential MLS® # 12753419

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New
1437 N Dearborn Street, Chicago, 60610

$3,750,000

1437 N Dearborn Street, Chicago, 60610

5 Beds 4.5 Baths 5,500 SqFt Residential MLS® # 12750844

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New Open House
1524 N Astor Street, Chicago, 60610

$4,995,000

1524 N Astor Street, Chicago, 60610

3 Beds 5 Baths 6,500 SqFt Residential
Sun, Sep 13th, 2026 @ 11:30am - 1pm
MLS® # 12753134

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New
2018 N Seminary Avenue, Chicago, 60614

$7,250,000

2018 N Seminary Avenue, Chicago, 60614

5 Beds 8 Baths 7,200 SqFt Residential MLS® # 12743394

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New Contingent
2119 N Kenmore Avenue, Chicago, 60614

$3,590,000

2119 N Kenmore Avenue, Chicago, 60614

6 Beds 5.5 Baths 5,719 SqFt Residential MLS® # 12744849

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441 W Deming Place, Chicago, 60614

$5,595,000

441 W Deming Place, Chicago, 60614

5 Beds 4.5 Baths 5,664 SqFt Residential MLS® # 12740927

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2658 N Mildred Avenue, Chicago, 60614

$3,998,000

2658 N Mildred Avenue, Chicago, 60614

6 Beds 6 Baths 6,400 SqFt Residential MLS® # 12740854

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New
3024 N Lake Shore Drive, Chicago, 60657

$7,495,000

3024 N Lake Shore Drive, Chicago, 60657

6 Beds 8 Baths 9,100 SqFt Residential MLS® # 12737250

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New
3026 N Lake Shore Drive, Chicago, 60657

$5,450,000

3026 N Lake Shore Drive, Chicago, 60657

6 Beds 8 Baths 9,100 SqFt Residential MLS® # 12737336

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New
1019 N Wolcott Avenue, Chicago, 60622

$4,995,000

1019 N Wolcott Avenue, Chicago, 60622

6 Beds 7 Baths 9,740 SqFt Residential MLS® # 12737324

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Contingent
2107 W Bradley Place, Chicago, 60618

$3,100,000

2107 W Bradley Place, Chicago, 60618

6 Beds 5 Baths 6,300 SqFt Residential MLS® # 12734737

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Contingent
1857 N Burling Street, Chicago, 60614

$3,999,000

1857 N Burling Street, Chicago, 60614

5 Beds 4.5 Baths 5,500 SqFt Residential MLS® # 12723191

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1901 W Cornelia Avenue, Chicago, 60657

$6,500,000

1901 W Cornelia Avenue, Chicago, 60657

5 Beds 5 Baths 10,000 SqFt Residential MLS® # 12719016

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Contingent
2026 N Clifton Avenue, Chicago, 60614

$4,450,000

2026 N Clifton Avenue, Chicago, 60614

6 Beds 6 Baths 5,200 SqFt Residential MLS® # 12716461

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New Contingent
2119 N Seminary Avenue, Chicago, 60614

$4,300,000

2119 N Seminary Avenue, Chicago, 60614

6 Beds 6.5 Baths 5,200 SqFt Residential MLS® # 12716177

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New
1878 N Orchard Street, Chicago, 60614

$6,950,000

1878 N Orchard Street, Chicago, 60614

5 Beds 6.5 Baths 9,512 SqFt Residential MLS® # 12705896

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1870 N Burling Street, Chicago, 60614

$5,695,000

↑ $195,000

1870 N Burling Street, Chicago, 60614

6 Beds 5 Baths 5,500 SqFt Residential MLS® # 12698186

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22 E Elm Street, Chicago, 60611

$5,995,000

22 E Elm Street, Chicago, 60611

11 Beds 5.5 Baths 5,100 SqFt Residential MLS® # 12686438

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1646 N Leavitt Street, Chicago, 60647

$4,850,000

1646 N Leavitt Street, Chicago, 60647

7 Beds 6.5 Baths 0 SqFt Residential MLS® # 12680743

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460 W Huron Street, Chicago, 60654

$6,450,000

460 W Huron Street, Chicago, 60654

7 Beds 9.5 Baths 10,360 SqFt Residential MLS® # 12278123

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1331 W Wolfram Street, Chicago, 60657

$3,975,000

1331 W Wolfram Street, Chicago, 60657

7 Beds 4.5 Baths 5,000 SqFt Residential MLS® # 12667378

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New
79 E Cedar Street, Chicago, 60611

$6,900,000

79 E Cedar Street, Chicago, 60611

4 Beds 7 Baths 7,523 SqFt Residential MLS® # 12658057

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1944 N Fremont Street, Chicago, 60614

$4,550,000

1944 N Fremont Street, Chicago, 60614

5 Beds 5.5 Baths 5,000 SqFt Residential MLS® # 12643241

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32 E Bellevue Place, Chicago, 60611

$4,500,000

↓ $950,000

32 E Bellevue Place, Chicago, 60611

6 Beds 5.5 Baths 6,000 SqFt Residential MLS® # 12646807

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Are you planning to buy or sell a home or condo in Chicago? Contact the Chicago Condo Finder Team, Chicago's local condo experts, for help navigating the current market conditions. Call or text (312) 953-0961 now to schedule a showing for a unit you'd like to preview!

Contact Us For more Info About Luxury Homes & Real Estate in Chicago

Chicago is home to a number of world-class luxury homes and condominiums. To schedule a private tour of your preferred properties, please contact our team of real estate specialists.