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

147 homes

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Recommended

$425,000

3 beds2 baths1,600 sq ft

860 N Lake Shore Dr Unit 8M, Chicago, IL 60611

On site management • 24 hr door staff • Lake michigan views

ABOUT THIS HOME
Vintage Home for sale in Downtown Chicago, IL:
* * 48 HOURS ADVANCED NOTICE REQUIRED TO TOUR OCCUPIED RESIDENCE. * * One, two, and three bedroom units available ranging from 1000-3700+ square feet. 709 is a 930 sq ft north facing 1 bedroom residence with 11' ceilings and 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 mol

$395,000

1 bed1 bath930 sq ft

850 N Lake Shore Dr #709, Chicago, IL 60611

Magnificent lobby • Heated indoor pool • Soaring ceilings

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. This spacious 3 bedroom plus family room and den lives like a single-family home in a full amenity building. 204 is a 3249 sq ft lake facing residence with 6 walk-in-closets, five fixture primary bath, 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 craftsmanshi

$1,455,000

3 beds2.5 baths3,249 sq ft

850 N Lake Shore Dr #204, Chicago, IL 60611

Magnificent lobby • Walk-in-closets • Soaring ceilings

ABOUT THIS HOME
Vintage Home for sale in Downtown Chicago, IL:
This spacious top-floor corner loft is located in the heart of the South Loop, one of Chicago's premier neighborhoods. Features include hardwood floors, soaring ceilings, an open floor plan, exposed brick, a gas fireplace, a private balcony, oversized windows, a walk-in closet, and in-unit washer/dryer. Ideally located-just a short walk to Lake Michigan, shopping, entertainment, restaurants, Mariano's, and express bus lines into the city. Garage parking is available for $25,000, and a storage cage is included. Pets welcome!

$255,000

1 bed1 bath934 sq ft

1528 S Wabash Ave #606, Chicago, IL 60605

Open floor plan • Exposed brick • Soaring ceilings

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. 1304 is a 1,040 sq ft one bedroom with lake views from every window, 9' ceilings, 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 stunni

$581,000

1 bed1 bath1,040 sq ft

850 N Lake Shore Dr #1304, Chicago, IL 60611

Magnificent lobby • Galley kitchen • Heated indoor pool

Property at 159 E Walton Pl Unit 7G, Chicago, IL 60611, 2 beds, 2.5 baths

$1,075,000

2 beds2.5 baths2,400 sq ft

159 E Walton Pl Unit 7G, Chicago, IL 60611

Property at 850 N Lake Shore Dr #1501, Chicago, IL 60611, 2 beds, 2 baths

$739,000

2 beds2 baths1,432 sq ft

850 N Lake Shore Dr #1501, Chicago, IL 60611

Property at 1631 S Michigan Ave #410, Chicago, IL 60616, 2 beds, 2 baths

$485,500

2 beds2 baths1,425 sq ft

1631 S Michigan Ave #410, Chicago, IL 60616

Property at 1120 N Lake Shore Dr Unit 18CD, Chicago, IL 60611, 4 beds, 3.5 baths

$999,500

4 beds3.5 baths— sq ft

1120 N Lake Shore Dr Unit 18CD, Chicago, IL 60611

Property at 411 W Ontario St #323, Chicago, IL 60654, 1 bed, 1 bath

$389,900

1 bed1 bath1,112 sq ft

411 W Ontario St #323, Chicago, IL 60654

Property at 1528 S Wabash Ave #405, Chicago, IL 60605, 1 bed, 1 bath

$239,800

1 bed1 bath— sq ft

1528 S Wabash Ave #405, Chicago, IL 60605

Property at 1500 N Lake Shore Dr Unit 23C, Chicago, IL 60610, 3 beds, 3.5 baths

$2,900,000

3 beds3.5 baths4,000 sq ft

1500 N Lake Shore Dr Unit 23C, Chicago, IL 60610

Property at 880 N Lake Shore Dr Unit 16G, Chicago, IL 60611, 1 bed, 1 bath

$160,000

1 bed1 bath750 sq ft

880 N Lake Shore Dr Unit 16G, Chicago, IL 60611

Property at 850 N Lake Shore Dr #201, Chicago, IL 60611, 2 beds, 2.5 baths

$1,017,000

2 beds2.5 baths2,464 sq ft

850 N Lake Shore Dr #201, Chicago, IL 60611

Property at 850 N Lake Shore Dr #803, Chicago, IL 60611, 1 bed, 1 bath

$699,000

1 bed1 bath1,255 sq ft

850 N Lake Shore Dr #803, Chicago, IL 60611

Property at 818 N Dearborn St Unit 1R, Chicago, IL 60610, 2 beds, 2 baths

$485,000

2 beds2 baths1,000 sq ft

818 N Dearborn St Unit 1R, Chicago, IL 60610

Property at 5 N Wabash Ave #1201, Chicago, IL 60602, 2 beds, 2 baths

$525,000

2 beds2 baths1,616 sq ft

5 N Wabash Ave #1201, Chicago, IL 60602

Property at 1540 N Lake Shore Dr Unit 8N, Chicago, IL 60610, 3 beds, 2.5 baths

$3,095,000

3 beds2.5 baths4,100 sq ft

1540 N Lake Shore Dr Unit 8N, Chicago, IL 60610

Property at 801 S Wells St #503, Chicago, IL 60607, 2 beds, 1 bath

$335,000

2 beds1 bath— sq ft

801 S Wells St #503, Chicago, IL 60607

Property at 400 E Randolph St #906, Chicago, IL 60601, 1 bath

$205,900

0 beds1 bath650 sq ft

400 E Randolph St #906, Chicago, IL 60601

Property at 1160 N Lasalle St, Chicago, IL 60610, 9 beds, 8 baths

$1,895,000

9 beds8 baths— sq ft

1160 N Lasalle St, Chicago, IL 60610

Property at Sign in for address, Chicago, IL 60611, 3 beds, 2 baths

$949,000

3 beds2 baths2,550 sq ft

Property at 1727 S Indiana Ave #214, Chicago, IL 60616, 2 beds, 2 baths

$399,999

2 beds2 baths1,822 sq ft

1727 S Indiana Ave #214, Chicago, IL 60616

Property at 861 N Lasalle St, Chicago, IL 60610, 5 beds, 6 baths

$3,249,995

5 beds6 baths7,480 sq ft

861 N Lasalle St, Chicago, IL 60610

Property at 6 S Clark St, Chicago, IL 60603

$2,995,000

— beds— baths18,306 sq ft

6 S Clark St, Chicago, IL 60603

Property at 1310 N Clybourn Ave, Chicago, IL 60610

$1,000,000

— beds— baths3,820 sq ft

1310 N Clybourn Ave, Chicago, IL 60610

Property at 1430 N Lake Shore Dr #12, Chicago, IL 60610, 6 beds, 5 baths

$1,000,000

6 beds5 baths5,000 sq ft

1430 N Lake Shore Dr #12, Chicago, IL 60610

Property at 880 N Lake Shore Dr Unit 4E, Chicago, IL 60611, 1 bed, 1 bath

$195,000

1 bed1 bath750 sq ft

880 N Lake Shore Dr Unit 4E, Chicago, IL 60611

Property at 740 S Federal St #1204, Chicago, IL 60605, 1 bed, 1 bath

$229,900

1 bed1 bath956 sq ft

740 S Federal St #1204, Chicago, IL 60605

Property at 880 N Lake Shore Dr Unit 17G, Chicago, IL 60611, 1 bed, 1 bath

$140,000

1 bed1 bath800 sq ft

880 N Lake Shore Dr Unit 17G, Chicago, IL 60611

Property at 1425 N State Pkwy, Chicago, IL 60610, 7 beds, 7.5 baths

$4,395,000

7 beds7.5 baths7,607 sq ft

1425 N State Pkwy, Chicago, IL 60610

Property at 900 N Lake Shore Dr #1904, Chicago, IL 60611, 1 bed, 1 bath

$264,999

1 bed1 bath876 sq ft

900 N Lake Shore Dr #1904, Chicago, IL 60611

Property at 540 N Lake Shore Dr #420, Chicago, IL 60611, 3 beds, 2.5 baths

$950,000

3 beds2.5 baths3,400 sq ft

540 N Lake Shore Dr #420, Chicago, IL 60611

Property at 1260 N Astor St #3, Chicago, IL 60610, 4 beds, 5 baths

$1,299,000

4 beds5 baths4,500 sq ft

1260 N Astor St #3, Chicago, IL 60610

Property at 880 N Lake Shore Dr Unit 17D, Chicago, IL 60611, 1 bed, 1 bath

$199,000

1 bed1 bath740 sq ft

880 N Lake Shore Dr Unit 17D, Chicago, IL 60611

Property at 680 N Lake Shore Dr #716, Chicago, IL 60611, 2 beds, 1.5 baths

$387,000

2 beds1.5 baths1,594 sq ft

680 N Lake Shore Dr #716, Chicago, IL 60611

Property at 680 N Lake Shore Dr #1103, Chicago, IL 60611, 2 beds, 2.5 baths

$995,000

2 beds2.5 baths2,340 sq ft

680 N Lake Shore Dr #1103, Chicago, IL 60611

Property at 6 N Michigan Ave #1505, Chicago, IL 60602, 1 bed, 1 bath

$320,000

1 bed1 bath— sq ft

6 N Michigan Ave #1505, Chicago, IL 60602

Property at 880 N Lake Shore Dr Unit 3H, Chicago, IL 60611, 1 bed, 1 bath

$137,000

1 bed1 bath785 sq ft

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

Property at 910 N Lake Shore Dr #2220, Chicago, IL 60611, 3 beds, 2 baths

$520,000

3 beds2 baths1,436 sq ft

910 N Lake Shore Dr #2220, Chicago, IL 60611

Property at 910 N Lake Shore Dr #1620, Chicago, IL 60611, 3 beds, 2 baths

$649,000

3 beds2 baths1,400 sq ft

910 N Lake Shore Dr #1620, Chicago, IL 60611

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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 147 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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