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

148 homes

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ABOUT THIS HOME
Vintage Home for sale in Downtown Chicago, IL:
Enjoy life in this iconic landmarked Mies Van Der Rohe Co-op building on Lake Shore Drive. Contemporary, minimalist design of glistening glass with stunning city views of the John Hancock in this spacious one bedroom and one bath corner unit will inspire you. There is a large bedroom suite with a beautiful mirrored wall of closets. Open dining area leads to an extra large living room with floor to ceiling corner windows. The white wood cabinetry and granite counters in the kitchen are perfect for the creative chef. Two closets and living room shelving provide great storage. This prime Streeterville location is walking distance to luxury shopping, fine restaurants, Northwestern Medical Cente

$137,000

1 bed1 bath785 sq ft

880 N Lake Shore Dr Unit 3H, Chicago, IL 60611

Open dining area • Large bedroom suite • $1,553 HOA

ABOUT THIS HOME
Vintage Home for sale in Downtown Chicago, IL:
Incredible opportunity to own or redevelop a historic, value-add property at the high-traffic corner of Wabash & Roosevelt in Chicago's vibrant South Loop. Formerly home to the iconic Wabash Tap and Koko Taylor's Blues Club, this three-story building offers approx. Ground floor is a fully built-out, second-generation bar/restaurant space with existing infrastructure, ideal for a new operator or concept. The upper floors are currently configured as apartments and can be converted into additional residential units, creative offices, or short-term rentals. Zoned DX-7, the site allows potential for residential, mixed-use, hospitality, office, or retail development. Located in a Transit-Or

$1,790,000

— beds— baths9,000 sq ft

1233 S Wabash Ave, Chicago, IL 60605

Zoned dx-7 • 4,275 sq ft lot • Built 1910

ABOUT THIS HOME
Vintage Home for sale in Downtown Chicago, IL:
Only Gold Coast offering of a grand and gracious pre-war co-op ready to customize into one of Chicago's finest residences. Located on the full and private twenty-second floor, this light-filled layout of 4,200 square feet enjoys lakefront vistas and views from four exposures. Indulge your every wish and create a stunning home steps to Michigan Avenue and walking distance to excellent private and public schools. One concept by Inspired Interiors features four en-suite bedrooms, a large kitchen that opens to a lakefront breakfast room, and an adjoining family room, and a laundry room. Additional features are three fireplaces with original marble mantles and 9'6" ceilings. There are only

$950,000

4 beds3.5 baths4,200 sq ft

1242 N Lake Shore Dr #22, Chicago, IL 60610

Lakefront vistas • Three fireplaces • Large kitchen

ABOUT THIS HOME
Vintage Home for sale in Downtown Chicago, IL:
Garage parking space for $30,000. Must be sold to resident in the building! The parking space is a deeded space but it is valet parking in this building.

$30,000

— beds— baths— sq ft

1445 N State Pkwy Unit P1-12, Chicago, IL 60610

Parking • Built 1960 • Listed 48 days

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. 206 is a 1658 sq ft two-bedroom with multi-purpose den, 9' ceilings, loads of closets, galley 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 s

$889,000

2 beds2 baths1,658 sq ft

850 N Lake Shore Dr #206, Chicago, IL 60611

Magnificent lobby • Multi-purpose den • Historical building

Property at 159 E Walton Pl Unit 5C, Chicago, IL 60611, 3 beds, 3.5 baths

$1,750,000

3 beds3.5 baths3,672 sq ft

159 E Walton Pl Unit 5C, Chicago, IL 60611

Property at 860 N Lake Shore Dr Unit 5M, Chicago, IL 60611, 3 beds, 2 baths

$597,000

3 beds2 baths1,600 sq ft

860 N Lake Shore Dr Unit 5M, Chicago, IL 60611

Property at 806 N Rush St, Chicago, IL 60611

$9,500,000

— beds— baths3,912 sq ft

806 N Rush St, Chicago, IL 60611

Property at 860 N Lake Shore Dr Unit 4M, Chicago, IL 60611, 2 beds, 2 baths

$595,000

2 beds2 baths1,600 sq ft

860 N Lake Shore Dr Unit 4M, Chicago, IL 60611

Property at 1447 N Dearborn St Unit 1N, Chicago, IL 60610, 4 beds, 4.5 baths

$4,900,000

4 beds4.5 baths5,215 sq ft

1447 N Dearborn St Unit 1N, Chicago, IL 60610

Property at 1447 N Dearborn St Unit 1S, Chicago, IL 60610, 4 beds, 4.5 baths

$3,500,000

4 beds4.5 baths3,725 sq ft

1447 N Dearborn St Unit 1S, Chicago, IL 60610

Property at 880 N Lake Shore Dr Unit 11D, Chicago, IL 60611, 1 bed, 1 bath

$235,000

1 bed1 bath— sq ft

880 N Lake Shore Dr Unit 11D, Chicago, IL 60611

Property at 880 N Lake Shore Dr Unit 19A, Chicago, IL 60611, 1 bed, 1 bath

$315,000

1 bed1 bath800 sq ft

880 N Lake Shore Dr Unit 19A, Chicago, IL 60611

Property at 1467 S Michigan Ave, Chicago, IL 60605

$2,900,000

— beds— baths20,000 sq ft

1467 S Michigan Ave, Chicago, IL 60605

Property at 124 W Polk St #707, Chicago, IL 60605, 2 beds, 1 bath

$325,000

2 beds1 bath1,200 sq ft

124 W Polk St #707, Chicago, IL 60605

Property at 1447 N Dearborn St Unit 2N, Chicago, IL 60610, 4 beds, 3.5 baths

$4,000,000

4 beds3.5 baths4,273 sq ft

1447 N Dearborn St Unit 2N, Chicago, IL 60610

Property at 159 E Walton Pl, Chicago, IL 60611, 4 beds, 4.5 baths

$8,900,000

4 beds4.5 baths7,880 sq ft

159 E Walton Pl, Chicago, IL 60611

Property at 229 E Lake Shore Dr Unit 10E, Chicago, IL 60611, 4 beds, 4 baths

$1,875,000

4 beds4 baths3,735 sq ft

229 E Lake Shore Dr Unit 10E, Chicago, IL 60611

Property at 900 N Lake Shore Dr #1211, Chicago, IL 60611, 1 bath

$255,000

0 beds1 bath645 sq ft

900 N Lake Shore Dr #1211, Chicago, IL 60611

Property at 159 E Walton Pl Unit 8C, Chicago, IL 60611, 2 beds, 2.5 baths

$1,350,000

2 beds2.5 baths— sq ft

159 E Walton Pl Unit 8C, Chicago, IL 60611

Property at 212 W Washington St Unit P5-28, Chicago, IL 60606

$27,000

— beds— baths— sq ft

212 W Washington St Unit P5-28, Chicago, IL 60606

Property at 812 N Dearborn St, Chicago, IL 60610

$3,950,000

— beds— baths10,084 sq ft

812 N Dearborn St, Chicago, IL 60610

Property at 880 N Lake Shore Dr Unit 14H, Chicago, IL 60611, 1 bed, 1 bath

$190,000

1 bed1 bath750 sq ft

880 N Lake Shore Dr Unit 14H, Chicago, IL 60611

Property at 8 W Monroe St Unit P-103, Chicago, IL 60603

$28,000

— beds— baths— sq ft

8 W Monroe St Unit P-103, Chicago, IL 60603

Property at 8 W Monroe St Unit P-94, Chicago, IL 60603

$28,000

— beds— baths— sq ft

8 W Monroe St Unit P-94, Chicago, IL 60603

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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.

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