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Browse Vintage Condos and Pre-War Co-ops For Sale, $500,000 - $750,000

$250,000 - $500,000 $500,000 - $750,000 $750,000 - $1,000,000
$1,000,000 - $2,000,000 $2,000,000 - $3,000,000 $3,000,000 - $5,000,000
$5,000,000 - $10,000,000
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431 W Oakdale Avenue 14a, Chicago, IL - $645,000

Residential, Attached Single
  • 2 Beds
  • 2 Baths
  • 1,718 SQFT
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Elegant High-floor 2br/2ba Vintage Condo In Distinguished Oakdale Towers. Flooded With Natural Light, This Beautifully Maintained Corner Home Features A Grand Foyer, Formal Living Room With Decorative Fireplace, Custom Mantle And Built-in Shelving...

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Photo of Listing #12739888 CONTINGENT

453 W Fullerton Parkway 2e, Chicago, IL - $625,000

Residential, Attached Single
  • 2 Beds
  • Baths
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Built In The Early 1900s By Acclaimed Chicago Architect Paul Gerhardt And Nestled On A Beautiful Tree-lined Street In The Heart Of East Lincoln Park, This Breathtaking Vintage 2-bedroom/1.5 Bath Home Showcases An Extraordinary Collection Of Origin...

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Photo of Listing #12707919 CONTINGENT

507 W Aldine Avenue 1b, Chicago, IL - $580,000

Residential, Attached Single
  • 2 Beds
  • 2 Baths
  • 1,250 SQFT
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Vintage Charm Meets Modern Luxury In This Beautifully Renovated Two-bedroom, Two-bath Home In A Classic East Lakeview Courtyard Building. Original Architectural Details - Including Arched Doorways, French-pane Windows, Crown Molding And Oak Hardwo...

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Photo of Listing #12732915

3750 N Lake Shore Drive 2c, Chicago, IL - $525,000

Residential, Attached Single
  • 3 Beds
  • 3 Baths
  • 2,200 SQFT
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Are You Ready To Own A Meticulously Updated Unit In One Of Chicago's Most Iconic And Sought After 1920s Vintage Co-op Buildings, Well Here's Your Chance! This Rarely Available, Fully Renovated C-unit Offers An Expansive 3-bedroom, 3-bath Layout De...

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Photo of Listing #12719736

1200 N Lake Shore Drive 404, Chicago, IL - $699,000

Residential, Attached Single
  • 1 Bed
  • 1 Bath
  • 1,166 SQFT
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Fabulous Recent Renovation Of This Corner One Bedroom In Iconic Benjamin Marshall Building. High End Kitchen Renovation Features A Jennair Induction Stove And A Fisher Paykel Refrigerator And A Charming Breakfast Nook. The Exquisite Marble Bath Ha...

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1448 N Lake Shore Drive 5b, Chicago, IL - $587,000

Residential, Attached Single
  • 3 Beds
  • Baths
  • 2,691 SQFT
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Rarely Available Home With Stunning Lake Views In One Of The Gold Coast's Premier Co-op Buildings. After Exiting Your Semi-private Elevator, Barrel Ceilings Greet You In The Spacious Entryway Of This 3 Bedroom, 3.5 Bath Home. Each Bedroom Has Ens...

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179 E Lake Shore Drive 19s, Chicago, IL - $525,000

Residential, Attached Single
  • 2 Beds
  • 2 Baths
  • 1,530 SQFT
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An Upper East Side Apartment In The Drake Tower - Benjamin Marshall's Masterpiece On East Lake Shore Drive. Elegantly Spacious 2-bedroom/2 Bath Is The Perfect Pied-a-terre. Flooded With Light, Soaring Ceilings W/crown Moldings, Hardwood Floors, ...

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3800 N Lake Shore Drive 3g, Chicago, IL - $560,000

Residential, Attached Single
  • 2 Beds
  • 2 Baths
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Experience Timeless Elegance In This East Lakeview Vintage Residence, Nestled Within An Intimate Pre-war Elevator Building With Just Two Homes Per Floor. Rich Herringbone Hardwood Floors Flow From The Gracious Foyer Into The Formal Living And Dini...

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Photo of Listing #12680701 CONTINGENT

1448 N Lake Shore Drive 3c, Chicago, IL - $589,000

Residential, Attached Single
  • 3 Beds
  • Baths
  • 2,520 SQFT
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Extraordinary Value In This Prestigious Gold Coast Co-op. Wonderful 3-bedroom 2.5 Bath Floorplan. Updated In A Clean And Classic Style With Stunning Vintage Features Still Intact. This Home Is In Pristine Move-in Condition, Flooded With Light From...

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227 E Delaware Place 8c, Chicago, IL - $575,000

Residential, Attached Single
  • 3 Beds
  • 3 Baths
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Set Within A Classic 1923 Cooperative Building In The Heart Of Streeterville, Just Steps From Chicago's Magnificent Mile, This Beautifully Maintained Residence Blends Vintage Character With Thoughtful Updates. A Gracious Reception Hall Welcomes Yo...

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Midwest Real Estate Data LLC Logo The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Sotheby's International Realty are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Listing information last updated on September 8th, 2026 at 7:30am CDT.