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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
$1,000,000 - $2,000,000 $2,000,000 - $3,000,000 $3,000,000 - $5,000,000
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Photo of Listing #12208920

1325 North Astor Street 2, Chicago, IL - $1,799,900

Residential, Attached Single
  • 3 Beds
  • 4 Baths
  • 4,300 SQFT
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A Truly Exquisite Vintage Home On One Of The Most Coveted Streets In Chicago. This Immaculate Gold Coast Condo Lives Like A Single Family Home With Approximately 4300 Sf Of Living Space All On One Level And Beautiful Tree-top Views From Every Wind...

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Photo of Listing #12421552

435 West Roslyn Place 2e, Chicago, IL - $850,000

Residential, Attached Single
  • 3 Beds
  • 2 Baths
  • 1,800 SQFT
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Sophistication Meets Modern Comfort In This Fully Remodeled East Lincoln Park Penthouse Duplex, Nestled In A Stunning Greystone On A Historic, Tree-lined Street. Just A Half Block From Lincoln Park, North Pond, And The Lakefront Path, This Sun-dre...

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Photo of Listing #12417897

2319 North Commonwealth Avenue 2e, Chicago, IL - $449,900

Residential, Attached Single
  • 2 Beds
  • 1 Baths
  • 1,000 SQFT
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This Turn Key 2-bedroom, 1-bathroom East Lincoln Park Condo Offers Approximately 1,000 Square Feet Of Comfortable Living Space In A Charming Vintage Building With South-facing Exposure And Peaceful Courtyard Views. The Well-appointed Kitchen Featu...

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Photo of Listing #12420681

189 East Lake Shore Drive Ph18, Chicago, IL - $7,250,000

Residential, Attached Single
  • 5 Beds
  • 6 Baths
  • 7,462 SQFT
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Amazing, Dramatic Penthouse In A Classic Vintage Building On East Lake Shore Drive! This Home Has Been Completely Renovated With Over 7400 Square Feet Of Luxurious Finishes And Offers Expansive Lake & City Views Plus 2 Terraces With 550 Square Fee...

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Photo of Listing #12419557

1120 North Lake Shore Drive 18cd, Chicago, IL - $999,500

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 Degoyer In 1924, This Stately All-brick Cooperative Is One Of...

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Photo of Listing #12412597

159 East Walton Place 5c, Chicago, IL - $1,750,000

Residential, Attached Single
  • 3 Beds
  • 4 Baths
  • 3,672 SQFT
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Extremely Large Floorplan At The Palmolive! 3672 Sq Ft Of Expansive Living.this 3 Bed 3.5 Bathroom Plus Den Is An Unbelievable Value And Looks North On To The Historic Drake Hotel. Gracious Double Door Entry Foyer Greets You Upon Entering This Uni...

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1500 North Lake Shore Drive 5b, Chicago, IL - $1,575,000

Residential, Attached Single
  • 2 Beds
  • 4 Baths
  • 3,200 SQFT
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Luxury Living At Chicago's Premier And Iconic Co-op, Designed By New York City Architect Rosario Candela Of Park Avenue Fame, The 1500 Lsd Building Is Truly Best In Class. The Apartment Has Large Grand Flowing Rooms With Treetop Lake Views, Stunni...

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1242 North Lake Shore Drive 4n, Chicago, IL - $925,000

Residential, Attached Single
  • 3 Beds
  • 3 Baths
  • 2,035 SQFT
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Move Right Into This Impeccably Renovated, Mint-condition Pre-war Co-op .....may Be Purchased Turn-key.......a Masterful Blend Of Timeless Elegance With Modern Refinement. Spanning Approximately 2,000 Square Feet, The Finest Enhancements Are Showc...

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1550 North State Parkway 801, Chicago, IL - $675,000

Residential, Attached Single
  • 2 Beds
  • 2 Baths
  • 2,200 SQFT
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Extraordinary Opportunity In The Gold Coast's Most Beautiful And Revered Condo Building. Designed By Benjamin Marshal This Iconic And Classic Stone And Terra Cotta Structure Sits At The Foot Of Lincoln Park. The 8th Floor Unit Has A Marvelous Floo...

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3750 North Lake Shore Drive 16h, Chicago, IL - $499,999

Residential, Attached Single
  • 2 Beds
  • 2 Baths
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Nestled Atop The Historic 1920s Beaux-arts Coop At 3750 N Lake Shore Drive, This Top-floor Penthouse Unit Is A Masterpiece For Art Deco Enthusiasts. Designed By Michelle Herman Of Marvin Herman & Associates Architectural Firm, This Residence Epito...

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2912 North Commonwealth Avenue 10cd, Chicago, IL - $1,100,000

Residential, Attached Single
  • 4 Beds
  • 4 Baths
  • 4,500 SQFT
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Welcome To 2912 North Commonwealth Avenue, Unit 10cd, A Rarely Available Private Full Floor 1920's Midrise Residence Located In Lakeview East. This Remarkable 4,500-square-foot Home Occupies An Entire Floor, Offering 4 Bedrooms And 3.1 Bathrooms, ...

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Photo of Listing #12405513 CONTINGENT

31 East Elm Street 3b, Chicago, IL - $900,000

Residential, Attached Single
  • 3 Beds
  • 2 Baths
  • 1,800 SQFT
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Welcome To This Beautifully Updated Top-floor Condo In The Heart Of Chicago's Gold Coast- Conveniently Located Near The Lakefront Path And Rush Street's Dining Scene. This Home Has Been Remodeled To Blend Modern Updates With Vintage Charm, Featuri...

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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 July 17th, 2025 at 11:24am CDT.