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Browse Vintage Condos and Pre-War Co-ops For Sale

$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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Photo of Listing #12692009 CONTINGENT

1210 N Astor Street 1b, Chicago, IL - $785,000

Residential, Attached Single
  • 3 Beds
  • 2 Baths
  • 1,985 SQFT
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Premiere Gold Coast Updated Vintage 3 Bedroom Condo! Positioned Along One Of The Most Iconic Residential Streets, This Exceptional Home Resides Within A Historic Boutique Building Originally Designed By Celebrated Chicago Architects William Holabi...

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Photo of Listing #12665122 CONTINGENT

2948 N Pine Grove Avenue 2, Chicago, IL - $825,000

Residential, Attached Single
  • 4 Beds
  • 2 Baths
  • 2,000 SQFT
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Absolutely Stunning 4 Bedroom, 2 Bath Duplex-up Penthouse In East Lakeview And Nettelhorst Elementary, Filled With Natural Light From A Two-story Wall Of Windows Facing Green Treetops Of A Quiet Side Street And In One Of The Most Coveted Locations...

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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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Photo of Listing #12485530 CONTINGENT

230 E Delaware Place 5e, Chicago, IL - $799,000

Residential, Attached Single
  • 3 Beds
  • 2 Baths
  • 2,550 SQFT
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A Classi Vintage Apartment In A Boutique Building. Nestled Off Of Michigan Avenue In Streeterville This Property Has One Of The Last Gardens In The Neighborhood. The Unit's Layout Is Perfectly Aligned With No Wasted Space. A Gracious Foyer Leads...

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1120 N Lake Shore Drive 18cd, Chicago, IL - $899,995

Residential, Attached Single
  • 4 Beds
  • Baths
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Experience The Pinnacle Of Refined City Living In This Extraordinary Penthouse Residence Overlooking Lake Michigan. Situated Within A Distinguished 1924 Cooperative Designed By Renowned Architect Robert Degolyer, This Remarkable 4-bedroom, 3.1-bat...

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3500 N Lake Shore Drive 3c, Chicago, IL - $1,000,000

Residential, Attached Single
  • 4 Beds
  • 3 Baths
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This Impeccably Maintained Home Exudes Elegance And Character With A Sprawling 3500 Sf Floor Plan And Exquisite Details At Every Turn Of This Meticulous Restoration Boasting Lovely Green Treetop Views In The Se Corner -the Most Premiere Tier In Th...

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199 E Lake Shore Drive 8w, Chicago, IL - $4,300,000

Residential, Attached Single
  • 3 Beds
  • Baths
  • 4,000 SQFT
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A Residence Curated Rather Than Renovated. This Extraordinary Residence Evolves The Elegance Of A Grand European Apartment Of Rare Refinement And Enduring Elegance. This Exceptional Duplex At 199 East Lake Shore Drive Evokes The Quiet Grandeur, E...

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Photo of Listing #12634167

1120 N Lake Shore Drive 18ab, Chicago, IL - $895,000

Residential, Attached Single
  • 4 Beds
  • 3 Baths
  • 3,500 SQFT
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Rarely Available! Northeast Corner Penthouse With Private Entrance In Highly Desired Vintage Gold Coast Building. Fabulous East And North Views Of The Lake And Lakefront From Many Rooms And The Terraces. Grand Unit With Cathedral Carved Wood Cei...

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Photo of Listing #12623681

2000 N Lincoln Park West Avenue 312, Chicago, IL - $385,000

Residential, Attached Single
  • 1 Bed
  • 1 Bath
  • 1,100 SQFT
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Exceptional Tier #12 Corner Residence Offering Approximately 1,100 Sq. Ft. Of Refined Living Space In One Of Lincoln Park's Most Distinguished Vintage Buildings. This Great Home Features Expansive Treetop Exposures, Abundant Natural Light, And Cla...

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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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Photo of Listing #12607479 CONTINGENT

220 E Walton Place 9w, Chicago, IL - $799,000

Residential, Attached Single
  • 4 Beds
  • 4 Baths
  • 2,965 SQFT
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Charming And Elegant 3000 Sq. Foot Vintage Home In The Historic Fugard And Knapp Building. Only Two Condos Per Floor In This Very Special 19 Unit Residence. This Spacious 4-bedroom Residence Offers An Ideal Split Floor Plan, With All Bedrooms Feat...

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Photo of Listing #12617349 CONTINGENT

1500 N Astor Street 6, Chicago, IL - $2,995,000

Residential, Attached Single
  • 2 Beds
  • Baths
  • 3,700 SQFT
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Experience The Ultimate Gold Coast Living In The Historic Patterson-mccormick Mansion! Just Featured In A 14-page Spread Of Traditional Home Magazine, This Home Does Not Disappoint! Spanning Nearly 3700 Square Feet, This Home Is The Epitome Of Cla...

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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 August 13th, 2026 at 12:47pm CDT.