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 Chicago Vintage Condos and Pre-War Co-op Apartments

Read more about co-ops

Chicago Vintage Condos for Sale

 Discover the world of Chicago's pre-war condominiums and co-ops. Designed by the most prominent architects of that time, the attention to detail is evident from the moment you enter the lobby. Inspired by European castles and chateaux, these luxury condos and co-ops feature rich wood paneling, imported stone floors, hand painted beams, and leaded windows..The apartments have house-like layouts with high ceilings, hardwood floors, fireplaces, and many with maid's room that serve as a perfect home office. If you are looking for a good value and a spacious home you won't quickly out-grow, take a look at vintage condos and pre-war co-ops.  

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

$250,000 - $500,000 $500,000 - $750,000 $750,000 - $1,000,000
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Photo of Listing #12542943

3300 North Lake Shore Drive 15a, Chicago, IL - $939,000

Residential, Attached Single
  • 3 Beds
  • 3 Baths
  • 2,300 SQFT
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Enjoy The Sweeping Views Of The Lake, Park, And Harbor From This Sophisticated, Elegant, And Completely Renovated And Beautifully Restored Pre-war Masterpiece On A High Floor Of An Elegant Pre-war Building In East Lakeview's Best Location. This Is...

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Photo of Listing #12491521 CONTINGENT

20 East Cedar Street 8a, Chicago, IL - $950,000

Residential, Attached Single
  • 3 Beds
  • 3 Baths
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Architecturally Significant And Rich With Character, This Dramatic Two-story Residence In A Classic Early 1920's Building Offers An Exceptional Opportunity To Create Your Dream Home. Unit 8a Features Incredible Light, Volume, And Square Footage, W...

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1120 North Lake Shore Drive 10c, Chicago, IL - $599,000

Residential, Attached Single
  • 2 Beds
  • 2 Baths
  • 1,435 SQFT
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Designer Inspired Co-op With The Charm Of The 1920's - Live At The Corner Of Elm And Lake Shore Drive In This Elegant 2-bedroom, 2 Bath Home With The Highest Level Of Finishes That Was Professionally Renovated In 2014. A Private Elevator Foyer Gre...

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Photo of Listing #12541669 CONTINGENT

26 East Scott Street 3, Chicago, IL - $835,000

Residential, Attached Single
  • 2 Beds
  • 3 Baths
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Experience The Charm Of A European-inspired Enclave On A Quiet, Tree-lined Gold Coast Street. This Intimate, Five-unit Elevator Building Offers A Rare Combination Of Privacy, Character, And Understated Elegance. Set On An Elevated First Floor, The...

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1120 North Lake Shore Drive 18cd, Chicago, IL - $949,500

Residential, Attached Single
  • 4 Beds
  • 4 Baths
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Step Into Elegance The Moment You Arrive At This Extraordinary 4-bedroom, 3.1-bathroom Penthouse Offering Breathtaking Views Of Lake Michigan. Designed By The Legendary Architect Robert Degolyer In 1924, This Stately All-brick Cooperative Is One O...

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Photo of Listing #12540347 CONTINGENT

73 East Elm Street 12d, Chicago, IL - $450,000

Residential, Attached Single
  • 2 Beds
  • 1 Baths
  • 1,200 SQFT
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Step Into Timeless Elegance With This Beautifully Preserved Vintage Condo, Located In A Classic Pre-war Boutique Building In The Heart Of The Gold Coast. A Welcoming Foyer Opens To Rich Dark Parquet Floors That Run Throughout The Unit. The Spaciou...

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880 North Lake Shore Drive 14cd, Chicago, IL - $650,000

Residential, Attached Single
  • 3 Beds
  • 2 Baths
  • 1,550 SQFT
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Step Into The Epitome Of Modernist Elegance With This Meticulously Rehabbed Southeast Facing Corner 3-bedroom, 2-bathroom Co-op At The Iconic Mies Van Der Rohe's 880 Lake Shore Drive. This Is Not Just A Home-it's A Masterpiece Of Timeless Design P...

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Photo of Listing #12544604 CONTINGENT

1430 North Lake Shore Drive 18, Chicago, IL - $2,599,000

Residential, Attached Single
  • 4 Beds
  • 5 Baths
  • 4,500 SQFT
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Experience Sweeping, Unobstructed Lake And Skyline Vistas From This 4,500 Sf Full-floor Home In A Premier Gold Coast Co-op Along Lake Shore Drive. This Residence Underwent A Complete Renovation In 2019, With Additional Updates In 2025 Making This ...

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Photo of Listing #12544233 CONTINGENT

3800 North Lake Shore Drive 11e, Chicago, IL - $400,000

Residential, Attached Single
  • 3 Beds
  • 2 Baths
  • 2,150 SQFT
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Estate Sale Opportunity - Spacious 3br Condo By The Lake! Welcome To Your New Home! This Jumbo-sized 3-bedroom, 2-bath Condo Offers Generous Living Space, Classic Vintage Charm, And Endless Potential To Make It Your Own. Featuring Hardwood Floors...

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1210 North Astor Street 1a, Chicago, IL - $1,190,000

Residential, Attached Single
  • 4 Beds
  • 4 Baths
  • 3,213 SQFT
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Vintage Character And Charm Enhanced With Complementary High End Finishes, This Impeccably Renovated And Restored 1897 Classic Maisonnette. Meticulous Floor To Ceiling Improvements Highlight This First Floor Duplex. Upon Opening The Massive Mahoga...

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Photo of Listing #12513591

220 East Walton Place 9w, Chicago, IL - $975,000

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 #12520717 CONTINGENT

3530 North Lake Shore Drive 11b, Chicago, IL - $600,000

Residential, Attached Single
  • 2 Beds
  • 2 Baths
  • 2,000 SQFT
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Modern Design Meets Timeless Pre-war Elegance In This Expansive 2 Bed + Den Home With Sweeping Views Of Lake Michigan And Belmont Harbor. Fully Updated With Designer Finishes, This Residence Offers The Rare Combination Of Historic Character, Conte...

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 Learn more about Chicago's luxury co-ops

What is a co-op apartment?
When you purchase a co-op apartment, you are purchasing shares of stock in a legal entity, usually an Illinois corporation, that owns the real estate. Along

Real estate

Chicago Streeterville Co-op Apartment Drake Tower

When it comes to understanding the full array of housing options in Chicago, you needn’t be confused when you are considering a choice among the “Big Three”— single-family homes, condominiums, and cooperative (co-op) apartments. Most people have a clear idea of what it means to buy a freestanding, single-family house; condominiums are a concept people can grasp in a simple phrase, “an apartment you own. Basically, a co-op is different from a condominium only in its legal and financial form— the essential idea of ownership is the same. But instead of being simply “an apartment you own,” you are purchasing shares of stock in a legal entity, usually an Illinois corporation, that owns the real estate. Along with the shares, you receive a Proprietary Lease that entitles you to occupy a certain unit. Instead of a deed, you own shares in the whole building. The concept for co-op apartments is rooted in historical notions of “economic democracy” that originated in European cities, promoting the idea that even in multi-unit buildings, monthly rent could be replaced with a possession and equity structure that mirrored the advantages of homeownership. In Chicago, co-ops were the first form of apartment ownership, built between 1911-1929. The first “high rises” along the lakefront, these classic high end vintage or pre-war buildings are renowned today for their grand and gracious floor plans and architecturally significant details, similar to the historical buildings and best addresses along New York’s Fifth and Park Avenues. A classic co-op conjures scale, grace, and elegance with lobbies and shared spaces that match the architecture and aesthetics of the homes within. High ceilings, classical millwork, original fireplaces with many still wood burning, formal dining and living rooms, lush libraries, bedroom suites, and large kitchens with butler’s pantries and maid’s rooms, the perfect size for today’s home office, hark back to a time when gracious living would not be compromised just because you resided twelve stories above ground. Square footage in co-ops rival that found in single family homes, and, with the lake, parks, and city skyline so near at hand, expansive views as well. The purchase options differ among co-ops, with a few cooperatives not permitting financing and others restricting borrowed amounts to 50% of appraised or purchase price. Further, banks don’t offer traditional mortgages on co-ops, but do have similar loan offerings that provide the same benefits. Shareholders in a cooperative also pay real estate taxes, but they do not receive individual tax bills. A single tax bill is issued to the corporation and shareholders’ proportional share of the total bill, based on the number of shares they own, is included in their monthly assessment, which explains why co-op assessments appear higher than condos. The co-op board approval process varies by building, but, in general, you will provide a confidential personal financial statement, sometimes, the first few pages of the most recent two years of tax returns, a narrative credit report, and several personal and professional letters of reference. After the co-op board has reviewed these documents, a personal interview is scheduled. As with the purchase of a condominium, co-op contracts also have an attorney approval and inspection contingency time frame and during this period you will receive all of the necessary documents to acquaint you with the structure and financial health of the cooperative. It is important to note, if you are considering the purchase of a co-op, that, in most cases, you will not be able to lease your apartment -Photo: Lobby of the Drake Tower Cooperative ~ 179 E Lake Shore Drive

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 February 6th, 2026 at 11:24pm CST.