Connect

Find us on...

Dashboard

Login using...

 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
$5,000,000 - $10,000,000
Map Save this Search
Sort listings by:Newest First
Photo of Listing #12511717

415 West Aldine Avenue 9d, Chicago, IL - $440,000

Residential, Attached Single
  • 2 Beds
  • 2 Baths
  • 1,811 SQFT
View details More Photos Save

Set In An Intimate Elevator Pre-war Building With Only Two Homes Per Floor, This Large Residence Offers Privacy, Scale, And Vintage Character In A Prime Lakeview East Location Steps From The Lakefront. A Gracious Barrel-vaulted Entry Gallery Leads...

Midwest Real Estate Data LLC Logo
Photo of Listing #12509564 CONTINGENT

229 East Lake Shore Drive 4w, Chicago, IL - $2,150,000

Residential, Attached Single
  • 3 Beds
  • 3 Baths
  • 3,600 SQFT
View details More Photos Save

This Completely Redesigned, Like-new Home Offers Sensational Living At A Prestigious East Lake Shore Drive Address! The Redesigned Interior, Completed By Hewitt Horn, Features Gracious Room Sizes And Modern Amenities, While Maintaining The Integri...

Midwest Real Estate Data LLC Logo
Photo of Listing #12509121

3800 North Lake Shore Drive 11e, Chicago, IL - $425,000

Residential, Attached Single
  • 3 Beds
  • 2 Baths
  • 2,150 SQFT
View details More Photos Save

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...

Midwest Real Estate Data LLC Logo
Photo of Listing #12508077 CONTINGENT

3530 North Lake Shore Drive 10a, Chicago, IL - $649,900

Residential, Attached Single
  • 3 Beds
  • 3 Baths
  • 2,400 SQFT
View details More Photos Save

Come Check Out The Breathtaking Views Of Lake Michigan From This Gorgeous Condo Housed Within A Stunning Vintage Elevator Building On Lake Shore Dr! With Just 2 Units Per Floor, This 3 Bed, 3 Bath, Corner Unit Has Everything That You're Looking Fo...

Midwest Real Estate Data LLC Logo

20 East Cedar Street 2c, Chicago, IL - $985,000

Residential, Attached Single
  • 2 Beds
  • 3 Baths
  • 2,450 SQFT
View details More Photos Save

Set In A Lush, Park-like Courtyard On Prestigious Cedar Street, This One-of-a-kind Duplex Residence Blends Pre-war Grandeur With Modern Updates. Enter Through A Gracious Foyer That Opens To A Soaring Two-story Living Room With Gas Fireplace And Dr...

Midwest Real Estate Data LLC Logo

1325 North Astor Street 2, Chicago, IL - $1,720,000

Residential, Attached Single
  • 3 Beds
  • 4 Baths
  • 4,300 SQFT
View details More Photos Save

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...

Midwest Real Estate Data LLC Logo
Photo of Listing #12486789 CONTINGENT

1658 North Sedgwick Street 3n, Chicago, IL - $439,000

Residential, Attached Single
  • 2 Beds
  • 1 Baths
  • 1,150 SQFT
View details More Photos Save

Beautiful Vintage North And East-facing Condo In Old Town Triangle That Has Not Been On The Market In Over 35 Years! This Two-bedroom, One-bathroom, Third Floor Walk-up Is In A Perfect Location. Steps Away From Lasalle Language Academy And A Short...

Midwest Real Estate Data LLC Logo

3534 North Lake Shore Drive 6d, Chicago, IL - $495,000

Residential, Attached Single
  • 3 Beds
  • 2 Baths
  • 1,800 SQFT
View details More Photos Save

You Simply Must See This Sprawling 3 Br/2ba Home Perfectly Situated Across The Lakefront With Lovely Tree Top Views And All The Vintage Pre-war Charm Your Heart Desires! Offering 1,800 Sq. Ft. Of Decadent Space, Soaring Ceilings, 3 Bedrooms, 2 Bat...

Midwest Real Estate Data LLC Logo

1329 North Dearborn Street 1, Chicago, IL - $995,000

Residential, Attached Single
  • 3 Beds
  • 3 Baths
  • 3,000 SQFT
View details More Photos Save

Open Canceled For 11/2, Seller Accepted Contract | Located In The Heart Of Chicago's Prestigious Gold Coast Along Picturesque Dearborn Parkway, This 3-bedroom, 3-bath Home Offers Timeless Character In One Of The City's Most Desirable Neighborhoods...

Midwest Real Estate Data LLC Logo

159 East Walton Place 6b, Chicago, IL - $699,999

Residential, Attached Single
  • 1 Bed
  • 2 Bath
  • 1,278 SQFT
View details More Photos Save

Welcome To The Palmolive Building, One Of Chicago's Most Iconic Addresses. This One-bedroom, One-and-a-half-bathroom Home At 159 E Walton Place, Unit 6b, Is The Ideal Mix Of Classic Elegance And Modern Convenience. Whether You're Looking For A Ref...

Midwest Real Estate Data LLC Logo

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

Residential, Attached Single
  • 2 Beds
  • 2 Baths
  • 1,530 SQFT
View details More Photos Save

Magnificent Drake Tower Stunning 2-bedroom Residence Featuring Views Of Oak Street And Lake Shore Drive North. It Is A Combination Of History And Vintage Charm Along With The Comforts Of New Spacepak Central Ac;closets By Design In Primary, Guest...

Midwest Real Estate Data LLC Logo

1255 North State Parkway 2e-3e, Chicago, IL - $624,000

Residential, Attached Single
  • 2 Beds
  • 3 Baths
  • 1,493 SQFT
View details More Photos Save

Luxury Living Awaits In This Unique Duplex In The Historic 1924 Churchill Building In The Heart Of The Gold Coast. Located At State And Goethe, Residents Have Easy Access To Lincoln Park, Upscale Shopping, And Top-rated Dining. This Spacious Two-b...

Midwest Real Estate Data LLC Logo

 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 November 6th, 2025 at 9:53pm CST.