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:
Rare Historic Gem on Prestigious Astor Street. Step into a piece of Chicago's architectural legacy with this remarkable corner rowhome, designed in 1887 by the iconic firm Burnham & Root. Originally one of four distinguished residences showcasing the bold elegance of the Richardsonian Romanesque style, this home sits next to 1310 N. Astor-once the personal residence of John Wellborn Root, a founding figure of the Chicago School architecture style. Offering a rare opportunity to restore and reimagine, this property invites you to create a one-of-a-kind modern residence within an irreplaceable historic shell. Situated on a corner, sunlight pours into the home from its north, east, and w

$1,750,000

5 beds4 baths5,991 sq ft

1312 N Astor St, Chicago, IL 60610

Grand staircase • 10 foot ceilings • Corner rowhome

ABOUT THIS HOME
Vintage Home for sale in Downtown Chicago, IL:
New offer to customize this Heart of Gold Cost corner building only if you want to. This beautiful house is ready to move in, but it is also ready to be customized by the owner/developer, before closing. You don't have to worry about construction or design, just give us your ideas. Some pictures are digitally altered for the purpose of sharing what could be done. Let's begin with uniquely engineered suspended steel staircase, which can be reconstructed or can be surrounded with tampered glass. Imagine the 5500 sq. ft. house with elevator, done to your taste. Lower level bar, can be also transitioned to your specifications. The fifth proposed bedroom with its private bath could be built her

$3,395,000

5 beds5.5 baths5,500 sq ft

1401 N Astor St, Chicago, IL 60610

Glass catwalks • Exotic kitchen • Garage rooftop patio

NEW 15 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Downtown Chicago, IL:
Fully renovated in 2019, this south-facing 1-bedroom condo offers bright natural light, a protected south-facing view, hardwood floors, and a smart open layout in a full-amenity South Loop Chicago building. Assessments include building amenities and services such as heat, A/C, water, internet, cable, door staff, fitness center, rooftop deck, hot tub, party room, bike room, laundry, commissary, on-site management, lawn care, scavenger, and snow removal. Prime South Loop/downtown Chicago location near Lake Michigan, Millennium Park, dining, CTA, trains, and the Loop. Move-in ready.

$179,000

1 bed1 bath600 sq ft

40 E 9th St #1313, Chicago, IL 60605

Rooftop deck • Fitness center • Hot tub

ABOUT THIS HOME
Vintage Home for sale in Downtown Chicago, IL:
This bright and open soft loft features 12-foot ceilings and large windows. The unit includes one bedroom plus a den that can be utilized as an office. The kitchen features granite countertops, and there is a generous walk-in closet and in-unit laundry for added convenience. Additionally, a 6x9 storage closet is located on the same floor. The location is ideal, with easy access to shops, restaurants, public transportation, and Millennium Park. Please note that parking is not available in the building, but monthly parking is available nearby at the Millennium Park Garage.

$275,000

1 bed1 bath1,150 sq ft

5 N Wabash Ave #704, Chicago, IL 60602

Large windows • Walk-in closet • In-unit laundry

$485,000

2 beds2 baths1,545 sq ft

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

Corian counters • Miele appliances • Lake michigan views

Property at 1226 N Dearborn St Unit B, Chicago, IL 60610, 1 bed, 1.5 baths

$475,000

1 bed1.5 baths1,100 sq ft

1226 N Dearborn St Unit B, Chicago, IL 60610

Property at 55 E Elm St, Chicago, IL 60611, 4 beds, 4 baths

$2,185,000

4 beds4 baths4,222 sq ft

55 E Elm St, Chicago, IL 60611

Property at 1434 N Dearborn St, Chicago, IL 60610, 5 beds, 6 baths

$4,475,000

5 beds6 baths6,815 sq ft

1434 N Dearborn St, Chicago, IL 60610

Property at 900 N Kingsbury St #1025, Chicago, IL 60610, 2 beds, 2 baths

$449,900

2 beds2 baths1,256 sq ft

900 N Kingsbury St #1025, Chicago, IL 60610

Property at 161 W Harrison St Unit 1106-1108, Chicago, IL 60605, 3 beds, 3 baths

$660,000

3 beds3 baths2,800 sq ft

161 W Harrison St Unit 1106-1108, Chicago, IL 60605

Property at 1000 N Lake Shore Dr #2302, Chicago, IL 60611, 2 beds, 2 baths

$445,000

2 beds2 baths1,200 sq ft

1000 N Lake Shore Dr #2302, Chicago, IL 60611

Property at 1550 N Lake Shore Dr Unit 2A, Chicago, IL 60610, 2 beds, 2 baths

$429,900

2 beds2 baths1,327 sq ft

1550 N Lake Shore Dr Unit 2A, Chicago, IL 60610

Property at 300 W Grand Ave #209, Chicago, IL 60654, 2 beds, 2 baths

$549,000

2 beds2 baths1,300 sq ft

300 W Grand Ave #209, Chicago, IL 60654

Property at 159 E Walton Pl Unit 31A, Chicago, IL 60611, 3 beds, 3.5 baths

$5,995,000

3 beds3.5 baths5,500 sq ft

159 E Walton Pl Unit 31A, Chicago, IL 60611

Property at 1210 N Astor St Unit 1A, Chicago, IL 60610, 4 beds, 4 baths

$1,190,000

4 beds4 baths3,213 sq ft

1210 N Astor St Unit 1A, Chicago, IL 60610

Property at 1150 N Lake Shore Dr Unit 19A, Chicago, IL 60611, 2 beds, 2 baths

$544,900

2 beds2 baths1,400 sq ft

1150 N Lake Shore Dr Unit 19A, Chicago, IL 60611

Property at 310 S Michigan Ave #1900, Chicago, IL 60604, 3 beds, 3 baths

$849,000

3 beds3 baths2,000 sq ft

310 S Michigan Ave #1900, Chicago, IL 60604

Property at 801 S Wells St #608, Chicago, IL 60607, 1 bed, 1 bath

$265,000

1 bed1 bath950 sq ft

801 S Wells St #608, Chicago, IL 60607

Property at 680 N Lake Shore Dr #604, Chicago, IL 60611, 3 beds, 2.5 baths

$1,020,000

3 beds2.5 baths2,900 sq ft

680 N Lake Shore Dr #604, Chicago, IL 60611

Property at 850 N Lake Shore Dr #402, Chicago, IL 60611, 2 beds, 2 baths

$1,090,000

2 beds2 baths1,429 sq ft

850 N Lake Shore Dr #402, Chicago, IL 60611

Property at 850 N Lake Shore Dr #202, Chicago, IL 60611, 3 beds, 2.5 baths

$1,170,000

3 beds2.5 baths2,907 sq ft

850 N Lake Shore Dr #202, Chicago, IL 60611

Property at 253 E Delaware Pl Unit 14D, Chicago, IL 60611, 1 bath

$159,900

0 beds1 bath550 sq ft

253 E Delaware Pl Unit 14D, Chicago, IL 60611

Property at Sign in for address, Chicago, IL 60603, 2 beds, 2 baths

$330,000

2 beds2 baths1,100 sq ft

Property at 550 N Kingsbury St #316, Chicago, IL 60654, 2 beds, 1 bath

$417,900

2 beds1 bath1,030 sq ft

550 N Kingsbury St #316, Chicago, IL 60654

Property at 1445 N State Pkwy #1904, Chicago, IL 60610, 3 beds, 2 baths

$495,000

3 beds2 baths1,625 sq ft

1445 N State Pkwy #1904, Chicago, IL 60610

Property at 640 S Federal St #702, Chicago, IL 60605, 2 beds, 2 baths

$249,900

2 beds2 baths1,200 sq ft

640 S Federal St #702, Chicago, IL 60605

Property at 680 N Lake Shore Dr #1322, Chicago, IL 60611, 2 beds, 2.5 baths

$749,000

2 beds2.5 baths2,100 sq ft

680 N Lake Shore Dr #1322, Chicago, IL 60611

Property at 850 N Lake Shore Dr #301, Chicago, IL 60611, 1 bed, 1.5 baths

$594,000

1 bed1.5 baths1,416 sq ft

850 N Lake Shore Dr #301, Chicago, IL 60611

Property at 1252 N State Pkwy, Chicago, IL 60610, 5 beds, 6 baths

$1,999,000

5 beds6 baths5,000 sq ft

1252 N State Pkwy, Chicago, IL 60610

Property at 850 N Lake Shore Dr #608, Chicago, IL 60611, 1 bed, 1 bath

$646,000

1 bed1 bath1,286 sq ft

850 N Lake Shore Dr #608, Chicago, IL 60611

Property at 29 E Scott St, Chicago, IL 60610, 3 beds, 3.5 baths

$2,100,000

3 beds3.5 baths2,580 sq ft

29 E Scott St, Chicago, IL 60610

Property at 850 N Lake Shore Dr #305, Chicago, IL 60611, 2 beds, 2.5 baths

$1,395,000

2 beds2.5 baths2,179 sq ft

850 N Lake Shore Dr #305, Chicago, IL 60611

Property at 1632 S Indiana Ave #403, Chicago, IL 60616, 2 beds, 2 baths

$334,900

2 beds2 baths— sq ft

1632 S Indiana Ave #403, Chicago, IL 60616

Property at 1320 N State Pkwy Unit 14-15CD, Chicago, IL 60610, 5 beds, 6 baths

$3,595,000

5 beds6 baths7,750 sq ft

1320 N State Pkwy Unit 14-15CD, Chicago, IL 60610

Property at 1120 N Lake Shore Dr Unit 15A, Chicago, IL 60611, 3 beds, 2 baths

$750,000

3 beds2 baths1,800 sq ft

1120 N Lake Shore Dr Unit 15A, Chicago, IL 60611

Property at 431 S Dearborn St #1204, Chicago, IL 60605, 4 beds, 2 baths

$385,000

4 beds2 baths1,800 sq ft

431 S Dearborn St #1204, Chicago, IL 60605

Property at 680 S Federal St #903, Chicago, IL 60605, 1 bath

$150,000

0 beds1 bath600 sq ft

680 S Federal St #903, Chicago, IL 60605

Property at 888 S Michigan Ave #401, Chicago, IL 60605, 2 beds, 1 bath

$310,000

2 beds1 bath— sq ft

888 S Michigan Ave #401, Chicago, IL 60605

Property at 120 S State St #4, Chicago, IL 60603, 4 beds, 2 baths

$994,000

4 beds2 baths2,300 sq ft

120 S State St #4, Chicago, IL 60603

Property at 850 N Lake Shore Dr #1410, Chicago, IL 60611, 2 beds, 2 baths

$678,000

2 beds2 baths1,256 sq ft

850 N Lake Shore Dr #1410, Chicago, IL 60611

Property at 1150 N Lake Shore Dr Unit 9J, Chicago, IL 60611, 1 bath

$154,900

0 beds1 bath— sq ft

1150 N Lake Shore Dr Unit 9J, 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 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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