Chicago Vintage Condos For Sale

Vintage condos in Chicago offer an exceptional amount of charm and character, and the best part is that condo buyers should be able to find a vintage unit at nearly every single price range. If you're interested in vintage condos for sale in Chicago, check out what's currently on the market below, or narrow down your options by searching vintage condos by neighborhood using our vintage condo neighborhood directory below as well. 

Our vintage condo experts know the market inside and out and are happy to provide buyers with disclosures, past sales history, and dates and prices of vintage condos recently sold nearby, ensuring you're not only making the best decision but also getting the best price based on today's Chicago real estate market. View Chicago vintage condos by neighborhood.

Search Chicago Vintage Condos For Sale

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New

$679,900

1429 North Dearborn Street 2n, Chicago, 60610

2 Beds 2 Baths 0 SqFt Residential MLS® # 12495488

New

$158,000

5555 North Sheridan Road 130, Chicago, 60640

0 Beds 1 Bath 500 SqFt Residential MLS® # 12494683

New

$199,000

1157 East 56th Street 3, Chicago, 60637

2 Beds 1 Bath 0 SqFt Residential MLS® # 12494546

New

$420,000

6342 North Sheridan Road 5b, Chicago, 60660

3 Beds 2 Baths 1,950 SqFt Residential MLS® # 12491420

New

$800,000

3800 North Lake Shore Drive 2c, Chicago, 60613

3 Beds 3 Baths 2,800 SqFt Residential MLS® # 12487175

New

$249,000

11349 South Saint Lawrence Avenue Rowhse, Chicago, 60628

3 Beds 1 Bath 1,096 SqFt Residential MLS® # 12492728

$240,000

2649 West Haddon Avenue 2s, Chicago, 60622

1 Bed 1 Bath 0 SqFt Residential MLS® # 12489037

$499,000

5445 North Kenmore Avenue 1s, Chicago, 60640

3 Beds 3 Baths 1,700 SqFt Residential MLS® # 12492575

$245,000

7321 South South Shore Drive 8d, Chicago, 60649

3 Beds 3 Baths 2,000 SqFt Residential MLS® # 12488893

New

$369,000

106 North Aberdeen Street 5g, Chicago, 60607

1 Bed 2 Baths 0 SqFt Residential MLS® # 12491810

New Contingent

$299,000

4313 North Paulina Street 3, Chicago, 60613

2 Beds 1 Bath 1,000 SqFt Residential MLS® # 12490403

New

$2,900,000

1500 North Lake Shore Drive 23c, Chicago, 60610

3 Beds 4 Baths 4,000 SqFt Residential MLS® # 12482065

New

$259,000

1515 West Pratt Boulevard 1, Chicago, 60626

2 Beds 2 Baths 975 SqFt Residential MLS® # 12387040

New

$499,000

3826 North Fremont Street 1n, Chicago, 60613

2 Beds 2 Baths 0 SqFt Residential MLS® # 12483222

New

$1,295,000

2130 North Lincoln Park West Avenue 8n, Chicago, 60614

4 Beds 3 Baths 2,800 SqFt Residential MLS® # 12490806

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Search Chicago Condos By Type or Style

Continue searching the Chicago condo market and view listings by condo type or style using our popular search directory below. As Chicago condo experts, we know the local market and current market conditions better than anyone!

Continue Searching Chicago Vintage Condos

Not seeing a Chicago vintage condo listing that matches your search criteria here? Break down your search and browse vintage condos by neighborhood using our Chicago vintage condos directory below. 

What Makes a Vintage Chicago Condo So Desirable? 

Whether it’s a vintage courtyard building on Chicago’s north side or a vintage high-rise in the heart of downtown, vintage condos in Chicago have undeniable appeal, character, and desirability. While many low-rise and mid-rise vintage condo buildings in Chicago may lack all the fancy amenities you see in newer construction buildings, the upside is that they can be an affordable option for young and first-time home buyers looking for a longer-term solution over renting.

But suppose you’re a buyer who is still looking for a little luxury in a new place to call home. In that case, plenty of vintage condo buildings like The Palmolive or the countless co-ops lining Lake Shore Drive offer an upscale living experience that won’t disappoint. 

Chicago Vintage Condo Resources & Ways to Search Vintage Condos For Sale

• 3 Under-The-Radar Buildings For Searching Vintage Condos in Chicago
• Downtown Chicago's Top Vintage Condo Buildings
• The 3 Most Luxurious Vintage Condo Buildings in Chicago's Gold Coast Neighborhood
• Is The Palmolive Chicago's Most Impressive Vintage High-Rise Condo Building?

What to Expect When Buying a Vintage Condo in Chicago

Vintage condos in Chicago offer architectural character, detailed craftsmanship, and layouts that reflect early 20th-century design. You’ll find units with crown molding, hardwood floors, built-ins, and formal dining rooms in walk-up or mid-rise buildings.

Many are located in neighborhoods like Lakeview, Edgewater, Lincoln Park, and Hyde Park. While finishes and floor plans vary, these condos often include larger room sizes and shared courtyards or rooftop decks.

Buyers should be prepared to review building systems, reserve funding, and renovation history. Some vintage buildings have updated plumbing and electrical systems, while others still carry original components.

Because these properties tend to fall under smaller associations, maintenance and repair responsibilities can differ from those in newer high-rises. Our team helps buyers assess building condition, monthly costs, and long-term upkeep when comparing listings.

Who Typically Buys Vintage Condos in Chicago?

Vintage condo buyers often include first-time homeowners, design-focused professionals, and anyone who values architectural detail not commonly found in newer construction.

Many buyers are drawn to the craftsmanship, charm, and neighborhood locations of these buildings. Others choose vintage condos for the square footage and floor plans that allow separate living, dining, and work spaces.

Some buyers are relocating from other parts of the city and looking for long-term value within established residential areas. Others are downsizing but still want style and walkability near shops, parks, or public transportation. Whether you're drawn to pre-war finishes or looking for a solid association in a quiet neighborhood, we’ll help you identify buildings that balance age, condition, and monthly costs.

FAQs About Buying and Living in Vintage Condos in Chicago

What qualifies as a vintage condo?

Vintage condos are typically located in buildings constructed before 1940. Common features include original hardwood flooring, plaster walls, crown molding, and architectural details like arched doorways or decorative fireplaces.

Are vintage buildings less expensive than new construction?

Not always. While vintage condos may offer lower cost per square foot, pricing depends on location, condition, and whether building systems have been updated. Some are priced competitively with modern units in the same area.

What should I check before buying a vintage condo?

Review the condition of electrical systems, plumbing, windows, and the roof. It’s also important to assess reserves, planned assessments, and the association’s maintenance history. We’ll help you request and interpret this information.

Do vintage condos include modern amenities?

Some vintage buildings have added amenities like fitness rooms, shared laundry, or rooftop decks. Others maintain a minimal footprint to keep assessments low. We’ll clarify what’s included with each listing.

How do monthly HOA fees compare?

Monthly fees vary by building size, included utilities, and shared services. Some vintage condos include heat, water, and maintenance in one fee. We’ll help you compare costs and review budgets from each association.

Are vintage condos good for resale?

Well-maintained vintage units in strong locations typically hold value, especially those with updated systems and desirable floor plans. Buyers looking for long-term ownership often target these buildings.

Can I renovate a vintage condo?

Yes, but interior changes may require board approval. Some updates, like bathroom or kitchen renovations, are common. We’ll guide you through board procedures and help you understand what’s feasible based on the building’s structure.

Are there financing differences when buying a vintage condo?

In most cases, traditional financing applies. However, if the building has fewer units or limited reserves, lenders may require additional documentation. We’ll connect you with lenders familiar with older properties.

Contact me for help searching vintage condos in Chicago

If you love the charm and character of a vintage condo building in Chicago and you’re also ready to take your condo search to the next level, contact us at your earliest convenience to set up showings for available vintage condos you would like to see in person.

The Chicago Condo Finder team knows the vintage condo market better than anybody, ensuring we’ll find the perfect building for your unique situation and also negotiate the best deal possible based on current market conditions. Calling or texting us now only takes a second, so contact us now and start viewing properties ASAP!