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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 #12202654

1120 North Lake Shore Drive 12a, Chicago, IL - $512,500

Residential, Attached Single
  • 2 Beds
  • 2 Baths
  • 1,485 SQFT
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Enjoy Panoramic Lake And Sunrise Views From This Luxurious East-facing, High Floor 2 Bedroom, 2 Bath Coop! Highlights Include Beautiful Hardwood Floors, Newer Windows, A Gas Fireplace, And Crown Molding. Rather Than Drop Ceilings Or Install Unsigh...

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Photo of Listing #12343108

2600 North Lakeview Avenue 7e, Chicago, IL - $739,000

Residential, Attached Single
  • 2 Beds
  • 2 Baths
  • 2,300 SQFT
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Welcome To This One-of-a-kind, Oversized 2,300+ Sqft 2-bedroom, 2-bath Condo In The Iconic Marlborough Building, Designed By Robert Degolyer. This Fabulous Condo Is Larger Than Most Three-bedroom Residences! Situated In An Unbeatable Location Acro...

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Photo of Listing #12340255

3750 North Lake Shore Drive 2c, Chicago, IL - $600,000

Residential, Attached Single
  • 3 Beds
  • 3 Baths
  • 2,200 SQFT
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Vintage 1920s Building With Fabulous Views Of The Park (tennis, Golf, Restaurant, Beach, Belmont And Montrose Harbors, Play Ground Sanctuary...views Of Lake Michigan. **rare C Unit All Newly Remodeled. (250k ). Spectacular 3-bedroom/3-bath Residen...

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316 West Menomonee Street H, Chicago, IL - $775,000

Residential, Attached Single
  • 3 Beds
  • 2 Baths
  • 1,500 SQFT
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Nestled In The Charming Heart Of Old Town, This One-of-a-kind Coach House Lives Like A Single-family Home. Originally Built In 1932 As An Assyrian Church-once Claimed To Be The Tiniest Cathedral In The World-this Historic Gem Has Been Thoughtfully...

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257 East Delaware Place 7c, Chicago, IL - $450,000

Residential, Attached Single
  • 2 Beds
  • 2 Baths
  • 1,100 SQFT
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Live The Ultimate Chicago Dream At 257 E Delaware Place! Imagine Stepping Out Your Door And Being Moments From The Shimmering Waters Of Lake Michigan And The World-class Shopping And Dining Of Michigan Avenue. This Stunning 2-bedroom, 2-bathroom V...

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1242 North Lake Shore Drive 4n, Chicago, IL - $1,050,000

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 That Masterfully Blends Timeless Elegance With Modern Refinement. Spanning Approximately 2,000 Square Feet, The Finest Enhancements Are Showcased Throughout, Featuring Three ...

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1448 North Lake Shore Drive 19ab, Chicago, IL - $3,200,000

Residential, Attached Single
  • 5 Beds
  • 5 Baths
  • 5,000 SQFT
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Views, Views, Views From This Gorgeous Vintage Penthouse Co-op. Two Units Seamlessly Combined To Create A Fabulous 5 Bedroom, 4.5 Bath Home In The Sky At The Prestigious 1448 Co-op Building. Elevator Opens Directly Into The Unit With A Large Pr...

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Photo of Listing #12328444 CONTINGENT

64 East Elm Street 3, Chicago, IL - $2,095,000

Residential, Attached Single
  • 3 Beds
  • 4 Baths
  • 3,657 SQFT
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Live On One Of The Most Coveted Blocks In This Premier Gold Coast Locale! This Spacious Full Floor, One Level Home Offers 3600sf And Is The Perfect Single Family Home Alternative In A Gorgeous And Noteworthy Boutique Elevator Building. Bathed In N...

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Photo of Listing #12321047 CONTINGENT

1716 North Wells Street 3, Chicago, IL - $599,900

Residential, Attached Single
  • 3 Beds
  • 2 Baths
  • 1,507 SQFT
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Welcome To 1716 N Wells, Unit 3 - A Spacious And Beautifully Updated 3-bedroom, 2-bathroom Home In The Heart Of Chicago's Iconic Old Town Neighborhood. Perfectly Situated Just Steps From Lincoln Park, This Residence Offers The Best Of City Living ...

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Photo of Listing #12307906 CONTINGENT

1500 North Astor Street 7, Chicago, IL - $1,495,000

Residential, Attached Single
  • 3 Beds
  • 3 Baths
  • 3,700 SQFT
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Priced To Sell - Exquisite Luxury Full Floor Residence On Astor Street - Gold Coast Living At Its Finest! Discover The Timeless Elegance Of The Historic Patterson- Mccormick Mansion, Originally Designed In 1891 By Renowned Architect Stanford Whit...

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33 East Bellevue Place Ph-w7, Chicago, IL - $2,225,000

Residential, Attached Single
  • 3 Beds
  • 3 Baths
  • 3,425 SQFT
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Experience The Ultimate In Luxury Living In This Sensational Two Level True Penthouse, Nestled In The Heart Of The Best Gold Coast Locale. This Exquisite Residence Offers Exceptional Views From The 25x12 Terrace, As Well As A Sprawling 50x10 Deck,...

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Photo of Listing #12297304 CONTINGENT

1242 North Lake Shore Drive 13s, Chicago, IL - $1,050,000

Residential, Attached Single
  • 3 Beds
  • 5 Baths
  • 3,000 SQFT
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One Of The Most Elegant Buildings In The Gold Coast, 1242 Lsd Was Designed In 1929 By The Acclaimed Architect Robert Degolyer. The Larger Of Only Two Apartments On The 13th Floor, 13-s Offers Spectacular Views Of Lake Michigan And The Neighborhood...

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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 April 23rd, 2025 at 7:08am CDT.