Vintage homes for sale & real estate in Downtown Chicago, IL

148 homes

Sort:

Recommended

ABOUT THIS HOME
Vintage Home for sale in Downtown Chicago, IL:
Located in the heart of River North, this 1 bed / 1 bath loft has a great layout featuring exposed brick, timber beams, and hardwood floors throughout giving it a cool urban vibe. The combined living and dining area is bright and inviting. The renovated kitchen boasts sleek quartz countertops with a waterfall edge, stainless steel appliances, a wine fridge, and modern lighting. The large bedroom fits a king bed and has a full wall of closets. The updated bath is spacious and features on-trend tile. Facing Franklin Street, the unit is thoughtfully equipped with soundproof windows and insulated walls, ensuring peaceful living above the city and train. Additional highlights: in-unit laundry, n

$329,900

1 bed1 bath899 sq ft

225 W Huron St #516, Chicago, IL 60610

Timber beams • Quartz countertops • Exposed brick

OPEN TODAY, 10AM TO 3PM3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Downtown Chicago, IL:
One, two, and three bedroom units available ranging from 1000-3700+ square feet. 1302 is a 1429 sq ft lake facing two-bedroom with multi-purpose den, 9' ceilings, tons of closet space, and kitchen with all new SS Bosch kitchen appliances and new, in-unit Whirlpool washer and dryer. This beautifully renovated historical building, nestled along Chicago's picturesque lakefront, seamlessly combines timeless elegance with contemporary luxury. Step into the magnificent lobby, and you'll instantly be transported to a modern take on a classic, surrounded by exquisite architectural details that showcase the craftsmanship of this iconic structure. From intricately carved moldings to soaring ceilings

$880,000

2 beds2 baths1,429 sq ft

850 N Lake Shore Dr #1302, Chicago, IL 60611

Magnificent lobby • Multi-purpose den • Historical building

OPEN TODAY, 10AM TO 3PM

ABOUT THIS HOME
Vintage Home for sale in Downtown Chicago, IL:
One, two, and three bedroom units available ranging from 1000-3700+ square feet. 606 is a 1069 sq ft one bedroom with northeast facing view, 8'-6" ceilings, kitchen with all new SS Bosch kitchen appliances and new, in-unit Whirlpool washer and dryer. This beautifully renovated historical building, nestled along Chicago's picturesque lakefront, seamlessly combines timeless elegance with contemporary luxury. Step into the magnificent lobby, and you'll instantly be transported to a modern take on a classic, surrounded by exquisite architectural details that showcase the craftsmanship of this iconic structure. From intricately carved moldings to soaring ceilings adorned with stunning chand

$450,000

1 bed1 bath1,069 sq ft

850 N Lake Shore Dr #606, Chicago, IL 60611

Magnificent lobby • Heated indoor pool • Soaring ceilings

ABOUT THIS HOME
Vintage Home for sale in Downtown Chicago, IL:
Live Big in the Historic Prairie District - Converted Kodak Factory Loft! If you love character, space, and a location that puts Chicago's best playground right outside your door - welcome home. This 1519 sq ft timber loft in the iconic former Kodak building delivers the kind of scale and charm you just can't recreate today. We're talking 12-foot ceilings, massive rooms, exposed brick, gleaming oak hardwood flooring, and sunlight pouring in - the kind of real loft people dream about. A layout built to breathe, not squeeze. Every room is oversized, and the closets? Both bedrooms have walk-ins - plus an additional storage unit down the hall. Both bathrooms are fresh, neutral, and feature o

$359,900

2 beds2 baths1,519 sq ft

1727 S Indiana Ave #320, Chicago, IL 60616

Exposed brick • Oversized vanities • 12 foot ceilings

ABOUT THIS HOME
Vintage Home for sale in Downtown Chicago, IL:
DEEDED PARKING CLOSE TO EVERYTHING: LAKE MICHIGAN, SHOPPING, THEATERS, & MILLENIUM PARK. Valet service only 24/7

$16,000

— beds— baths— sq ft

8 W Monroe St Unit P001, Chicago, IL 60603

Lake michigan • Theaters • Millenium park

Property at 310 S Michigan Ave #1907, Chicago, IL 60604, 2 beds, 2 baths

$489,000

2 beds2 baths1,350 sq ft

310 S Michigan Ave #1907, Chicago, IL 60604

Property at 850 N Lake Shore Dr #1201, Chicago, IL 60611, 2 beds, 2 baths

$718,000

2 beds2 baths1,432 sq ft

850 N Lake Shore Dr #1201, Chicago, IL 60611

Property at 850 N Lake Shore Dr #1207, Chicago, IL 60611, 2 beds, 2 baths

$925,000

2 beds2 baths1,402 sq ft

850 N Lake Shore Dr #1207, Chicago, IL 60611

Property at 431 S Dearborn St #507, Chicago, IL 60605, 1 bed, 1 bath

$224,990

1 bed1 bath1,100 sq ft

431 S Dearborn St #507, Chicago, IL 60605

Property at 1550 N Lake Shore Dr Unit 32C, Chicago, IL 60610, 1 bed, 1 bath

$248,999

1 bed1 bath800 sq ft

1550 N Lake Shore Dr Unit 32C, Chicago, IL 60610

Property at 680 N Lake Shore Dr #1219, Chicago, IL 60611, 3 beds, 2.5 baths

$575,000

3 beds2.5 baths2,039 sq ft

680 N Lake Shore Dr #1219, Chicago, IL 60611

Property at 1544 N State Pkwy Unit 3A, Chicago, IL 60610, 3 beds, 2 baths

$495,000

3 beds2 baths1,800 sq ft

1544 N State Pkwy Unit 3A, Chicago, IL 60610

Property at 900 N Kingsbury St #835, Chicago, IL 60610, 2 beds, 2 baths

$399,000

2 beds2 baths— sq ft

900 N Kingsbury St #835, Chicago, IL 60610

Property at 850 N Lake Shore Dr #710, Chicago, IL 60611, 1 bed, 1 bath

$447,000

1 bed1 bath1,059 sq ft

850 N Lake Shore Dr #710, Chicago, IL 60611

Property at 212 W Washington St #1807, Chicago, IL 60606, 4 beds, 4 baths

$800,000

4 beds4 baths2,300 sq ft

212 W Washington St #1807, Chicago, IL 60606

Property at 850 N Lake Shore Dr #1306, Chicago, IL 60611, 1 bed, 1 bath

$532,000

1 bed1 bath1,031 sq ft

850 N Lake Shore Dr #1306, Chicago, IL 60611

Property at 310 S Michigan Ave #1612, Chicago, IL 60604, 1 bed, 1 bath

$295,000

1 bed1 bath765 sq ft

310 S Michigan Ave #1612, Chicago, IL 60604

Property at 253 E Delaware Pl Unit 20G-E, Chicago, IL 60611, 2 beds, 2 baths

$299,000

2 beds2 baths1,238 sq ft

253 E Delaware Pl Unit 20G-E, Chicago, IL 60611

Property at 642 N Dearborn St, Chicago, IL 60654

$2,150,000

— beds— baths— sq ft

642 N Dearborn St, Chicago, IL 60654

Property at 850 N Lake Shore Dr #1005, Chicago, IL 60611, 2 beds, 2 baths

$1,025,000

2 beds2 baths1,737 sq ft

850 N Lake Shore Dr #1005, Chicago, IL 60611

Property at 780 S Federal St #1202, Chicago, IL 60605, 1 bath

$199,000

0 beds1 bath660 sq ft

780 S Federal St #1202, Chicago, IL 60605

Property at 1400 N State Pkwy Unit 18A, Chicago, IL 60610, 2 beds, 2 baths

$475,000

2 beds2 baths1,250 sq ft

1400 N State Pkwy Unit 18A, Chicago, IL 60610

Property at 1438 N Dearborn St, Chicago, IL 60610, 5 beds, 7 baths

$6,500,000

5 beds7 baths— sq ft

1438 N Dearborn St, Chicago, IL 60610

Property at 1550 N State Pkwy Unit LIB-ABC, Chicago, IL 60610, 6 beds, 8 baths

$4,995,000

6 beds8 baths8,500 sq ft

1550 N State Pkwy Unit LIB-ABC, Chicago, IL 60610

Property at 1000 N Lake Shore Dr #804, Chicago, IL 60611, 1 bed, 1 bath

$214,999

1 bed1 bath— sq ft

1000 N Lake Shore Dr #804, Chicago, IL 60611

Property at 225 W Huron St #403, Chicago, IL 60654, 1 bed, 1 bath

$250,000

1 bed1 bath— sq ft

225 W Huron St #403, Chicago, IL 60654

Property at 1448 N Lake Shore Dr Unit 9A, Chicago, IL 60611, 3 beds, 3 baths

$599,000

3 beds3 baths— sq ft

1448 N Lake Shore Dr Unit 9A, Chicago, IL 60611

Property at 1255 N State Pkwy Unit 2B, Chicago, IL 60610, 2 beds, 1 bath

$399,000

2 beds1 bath— sq ft

1255 N State Pkwy Unit 2B, Chicago, IL 60610

Property at 1500 N Astor St #6, Chicago, IL 60610, 2 beds, 2.5 baths

$3,300,000

2 beds2.5 baths3,700 sq ft

1500 N Astor St #6, Chicago, IL 60610

Property at 6 E Monroe St #1403, Chicago, IL 60603, 1 bed, 1 bath

$229,000

1 bed1 bath700 sq ft

6 E Monroe St #1403, Chicago, IL 60603

Property at 124 W Polk St #100, Chicago, IL 60605, 3 beds, 2 baths

$625,000

3 beds2 baths2,200 sq ft

124 W Polk St #100, Chicago, IL 60605

Property at 330 S Michigan Ave #2006, Chicago, IL 60604, 2 beds, 2.5 baths

$499,000

2 beds2.5 baths1,600 sq ft

330 S Michigan Ave #2006, Chicago, IL 60604

Property at 915 N Dearborn St, Chicago, IL 60610, 6 beds, 6 baths

$18,500,000

6 beds6 baths13,400 sq ft

915 N Dearborn St, Chicago, IL 60610

Property at 53 E Division St, Chicago, IL 60610, 5 beds, 7 baths

$3,999,000

5 beds7 baths7,500 sq ft

53 E Division St, Chicago, IL 60610

Property at 910 N Lake Shore Dr #1415, Chicago, IL 60611, 1 bed, 1 bath

$280,000

1 bed1 bath841 sq ft

910 N Lake Shore Dr #1415, Chicago, IL 60611

Property at 40 E 9th St #1303, Chicago, IL 60605, 1 bed, 1 bath

$199,000

1 bed1 bath900 sq ft

40 E 9th St #1303, Chicago, IL 60605

Property at 850 N Lake Shore Dr #807, Chicago, IL 60611, 2 beds, 2 baths

$895,000

2 beds2 baths1,402 sq ft

850 N Lake Shore Dr #807, Chicago, IL 60611

Property at 531 S Plymouth Ct #602, Chicago, IL 60605, 2 beds, 2 baths

$535,000

2 beds2 baths2,400 sq ft

531 S Plymouth Ct #602, Chicago, IL 60605

Property at 154 W Hubbard St #603, Chicago, IL 60654, 2 beds, 2 baths

$1,450,000

2 beds2 baths2,284 sq ft

154 W Hubbard St #603, Chicago, IL 60654

Property at 360 W Illinois St #614, Chicago, IL 60654, 2 beds, 2 baths

$725,000

2 beds2 baths— sq ft

360 W Illinois St #614, Chicago, IL 60654

Property at 189 E Lake Shore Dr Ph 18, Chicago, IL 60611, 5 beds, 5.5 baths

$7,250,000

5 beds5.5 baths7,462 sq ft

189 E Lake Shore Dr Ph 18, Chicago, IL 60611

Viewing page 2 of 4

Based on information submitted to the MLS GRID as of Tue Dec 23 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in Downtown Chicago

There are currently 148 vintage homes for sale in Downtown Chicago at a median listing price of $499K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Downtown Chicago stay on the market for 88 days and receive 2 offers. Popular neighborhoods include Lincoln Park, Lake View, Bucktown, Wicker Park, and West Loop. This map is refreshed with the newest listings in Downtown Chicago every 15 minutes.

In the past month, 227 homes have been sold in Downtown Chicago. In addition to houses in Downtown Chicago, there were also 1366 condos, 32 townhouses, and 1 multi-family unit for sale in Downtown Chicago last month. Find your dream home in Downtown Chicago using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Downtown Chicago are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Downtown Chicago. If you're looking to sell your home in the Downtown Chicago area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Downtown Chicago with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Downtown Chicago, IL

Nearby Neighborhoods

Cities

Nearby Neighborhoods with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in Downtown Chicago, IL

How to buy a house in Downtown Chicago, IL

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Illinois

Chicago homes for sale
$335,000
Naperville homes for sale
$699,000
Schaumburg homes for sale
$299,000
Arlington Heights homes for sale
$439,000
Glenview homes for sale
$719,000
Oak Park homes for sale
$349,500
Evanston homes for sale
$407,500
Des Plaines homes for sale
$385,000
Orland Park homes for sale
$368,900
Downers Grove homes for sale
$487,450
Mount Prospect homes for sale
$409,999
Glen Ellyn homes for sale
$524,500
St. Charles homes for sale
$449,995
Skokie homes for sale
$449,000
Lombard homes for sale
$375,000

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.