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Douglas, Chicago, IL - homes for sale
69 of 69 results displayed
- Open Sat, 1 to 3pmNew
$164,999Active2 beds 2 baths1,100 sq. ft.3021 S Michigan Avenue #306, Chicago, IL 60616
MLS# 12673594Listed by: AIHOME REALTY GROUP LLC
- New
$304,999Active3 beds 2 baths1,500 sq. ft.3629 S Giles Avenue #4, Chicago, IL 60653
MLS# 12673213Listed by: REAL BROKER LLC - New
$549,000Active6 beds 4 baths3,389 sq. ft.3633 S Giles Avenue, Chicago, IL 60653
MLS# 12669141Listed by: COMPASS - New
$279,000Active2 beds 2 baths1,136 sq. ft.3506 S State Street #303, Chicago, IL 60609
MLS# 12653021Listed by: CENTURY 21 REALTY ASSOCIATES - New
$99,900Active0 Acres3808 S Wabash Avenue, Chicago, IL 60653
MLS# 12644489Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE - New
$585,000Active4 beds 4 baths1,656 sq. ft.3651 S Giles Avenue, Chicago, IL 60653
MLS# 12667250Listed by: UNITED REAL ESTATE - CHICAGO - New
$140,000Active-- beds 1 baths420 sq. ft.601 E 32nd Street #403, Chicago, IL 60616
MLS# 12668825Listed by: LUXESQUIRE REALTY - New
$224,900Active2 beds 2 baths1,500 sq. ft.25 E 26th Street, Chicago, IL 60616
MLS# 12667653Listed by: HOMES REALTY OF CHICAGO INC - New
$235,000Active2 beds 2 baths1,200 sq. ft.3560 S Giles Avenue, Chicago, IL 60653
MLS# 12559822Listed by: ESM REALTY GROUP - New
$359,000Active2 beds 2 baths1,121 sq. ft.2545 S Dearborn Street #331, Chicago, IL 60616
MLS# 12657789Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE - New
$342,000Active2 beds 2 baths1,288 sq. ft.317 E 25th Street #3E, Chicago, IL 60616
MLS# 12667098Listed by: JAMESON SOTHEBY'S INTL REALTY - New
$110,000Active-- beds 1 baths600 sq. ft.3001 S Michigan Avenue #1006, Chicago, IL 60616
MLS# 12665086Listed by: O W AUCTION GROUP LLC 
$439,900Pending4 beds 3 baths2,400 sq. ft.2733 S Michigan Avenue #A, Chicago, IL 60616
MLS# 12657426Listed by: COLDWELL BANKER REALTY
$574,900Pending5 beds 5 baths3,488 sq. ft.3640 S Prairie Avenue, Chicago, IL 60653
MLS# 12654600Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$0Active1 beds 1 baths800 sq. ft.606 E Woodland Avenue #211, Chicago, IL 60616
MLS# 12657841Listed by: PARKVUE REALTY CORPORATION
$144,000Active1 beds 1 baths750 sq. ft.2605 S Indiana Avenue #708, Chicago, IL 60616
MLS# 12654940Listed by: CENTURY 21 S.G.R., INC.
$3,500Active0 Acres50 E 26th Street #PU-61, Chicago, IL 60616
MLS# 12653043Listed by: AVENUE 1 REALTY GROUP
$259,000Active2 beds 1 baths1,020 sq. ft.3506 S State Street #308, Chicago, IL 60609
MLS# 12652714Listed by: CENTURY 21 REALTY ASSOCIATES
$119,000Active-- beds 1 baths440 sq. ft.2901 S Michigan Avenue #506, Chicago, IL 60616
MLS# 12651479Listed by: MAGIERA CITY LLC
$475,000Pending3 beds 3 baths2,156 sq. ft.3123 S Michigan Avenue, Chicago, IL 60616
MLS# 12585127Listed by: BAIRD & WARNER
$359,000Pending2 beds 2 baths1,100 sq. ft.2545 S Dearborn Street #705, Chicago, IL 60616
MLS# 12608580Listed by: BAIRD & WARNER
$115,000Active-- beds 1 baths460 sq. ft.3021 S Michigan Avenue #311, Chicago, IL 60616
MLS# 12618386Listed by: INFINITI PROPERTIES, INC.
$219,999Active2 beds 1 baths780 sq. ft.3506 S State Street #312, Chicago, IL 60616
MLS# 12647391Listed by: YOUMU VENTURES LLC
$149,900Active1 beds 1 baths790 sq. ft.2901 S Michigan Avenue #505, Chicago, IL 60616
MLS# 12641083Listed by: BERKSHIRE HATHAWAY HOMESERVICES CHICAGO
$225,000Active2 beds 2 baths1,500 sq. ft.601 E 32nd Street #800, Chicago, IL 60616
MLS# 12640596Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$342,000Pending2 beds 2 baths1,171 sq. ft.2545 S Dearborn Street #507, Chicago, IL 60616
MLS# 12642269Listed by: JAMESON SOTHEBY'S INTL REALTY
$496,000Active3 beds 3 baths2,469 sq. ft.3560 S Federal Street, Chicago, IL 60609
MLS# 12643445Listed by: CENTURY 21 REALTY ASSOCIATES
$299,900Active2 beds 2 baths1,500 sq. ft.19 E 26th Street #1, Chicago, IL 60616
MLS# 12640751Listed by: BEYCOME BROKERAGE REALTY LLC
$125,000Active-- beds 1 baths440 sq. ft.2901 S Michigan Avenue #1301, Chicago, IL 60616
MLS# 12639173Listed by: CIRCLE ONE REALTY- $79,000Active0 Acres
24 E 37th Place, Chicago, IL 60653
MLS# 12637869Listed by: STARWOOD REAL ESTATE LLC 
$139,500Active1 beds 1 baths727 sq. ft.2605 S Indiana Avenue #1208, Chicago, IL 60616
MLS# 12636667Listed by: DARKO TESANOVIC
$175,000Pending2 beds 2 baths1,100 sq. ft.3021 S Michigan Avenue #406, Chicago, IL 60616
MLS# 12631702Listed by: REAL BROKER LLC
$399,000Active2 beds 2 baths3105 S Giles Avenue #1S, Chicago, IL 60616
MLS# 12635115Listed by: COMPASS
$339,000Active3 beds 2 baths1,500 sq. ft.16 W 36th Street, Chicago, IL 60609
MLS# 12627182Listed by: KELLER WILLIAMS INFINITY
$125,000Active1 beds 1 baths800 sq. ft.2901 S Michigan Avenue #1610, Chicago, IL 60616
MLS# 12623380Listed by: KALE REALTY
$579,000Active2 beds 3 baths2,185 sq. ft.350 E Eastgate Place, Chicago, IL 60616
MLS# 12619160Listed by: CENTURY 21 CIRCLE
$165,000Active2 beds 1 baths1,200 sq. ft.3001 S Michigan Avenue #1707, Chicago, IL 60616
MLS# 12618807Listed by: COLDWELL BANKER REALTY
$160,000Active1 beds 1 baths760 sq. ft.2605 S Indiana Avenue #1008, Chicago, IL 60616
MLS# 12613517Listed by: COMPASS
$149,900Pending2 beds 2 baths1,325 sq. ft.2605 S Indiana Avenue #402, Chicago, IL 60616
MLS# 12618006Listed by: KELLER WILLIAMS PREFERRED RLTY
$1,248,888Active9 beds 9 baths3762 S Indiana Avenue, Chicago, IL 60653
MLS# 12606301Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$190,000Active2 beds 2 baths1,500 sq. ft.2605 S Indiana Avenue #302, Chicago, IL 60616
MLS# 12608656Listed by: REAL PEOPLE REALTY
$399,000Pending0 Acres300 E Pershing Road, Chicago, IL 60653
MLS# 12606489Listed by: CHICAGO REAL ESTATE RESOURCES
$299,900Pending2 beds 2 baths1,277 sq. ft.347 E 25th Place #1E, Chicago, IL 60616
MLS# 12572259Listed by: BAIRD & WARNER
$154,000Active1 beds 1 baths727 sq. ft.2605 S Indiana Avenue #1909, Chicago, IL 60616
MLS# 12599594Listed by: DARKO TESANOVIC
$90,000Active-- beds 1 baths600 sq. ft.2921 S Michigan Avenue #413, Chicago, IL 60616
MLS# 12597302Listed by: KALE REALTY
$200,000Active3 beds 2 baths1,700 sq. ft.601 E 32nd Street #1001, Chicago, IL 60616
MLS# 12591875Listed by: COLDWELL BANKER REALTY
$109,900Active0.05 Acres310 E Pershing Road, Chicago, IL 60653
MLS# 12593016Listed by: NELLY CORP REALTY
$389,900Active6 beds 3 baths3,230 sq. ft.3143 S Giles Avenue, Chicago, IL 60616
MLS# 12591764Listed by: PARKVUE REALTY CORPORATION
$949,900Pending4 beds 4 baths3,285 sq. ft.Address Withheld By Seller, Chicago, IL 60616
MLS# 12588515Listed by: PAMELA HOLT- $175,000Active0 Acres
3423 S Calumet Avenue, Chicago, IL 60616
MLS# 12588286Listed by: COMPASS 
$150,000Pending1 beds 1 baths2901 S Michigan Avenue #1909, Chicago, IL 60616
MLS# 12584609Listed by: REDFIN CORPORATION
$330,000Active6 beds 2 baths2,204 sq. ft.3549 S Indiana Avenue, Chicago, IL 60653
MLS# 12581786Listed by: ILLINOIS REAL ESTATE PARTNERS
$349,900Active0 Acres3364 S Giles Avenue, Chicago, IL 60616
MLS# 12581356Listed by: COMPASS
$1,200,000Pending8 beds 10 baths11,108 sq. ft.3736 S Michigan Avenue, Chicago, IL 60653
MLS# 12580025Listed by: COMPASS
$110,000Pending1 beds 1 baths900 sq. ft.606 E Woodland Park Avenue #105, Chicago, IL 60616
MLS# 12567005Listed by: TAYLOR REALTY GROUP LLC
$150,000Active1 beds 1 baths695 sq. ft.345 E Eastgate Place #604, Chicago, IL 60616
MLS# 12547829Listed by: BEST CHICAGO PROPERTIES, LLC
$170,000Pending2 beds 2 baths1,244 sq. ft.2901 S Michigan Avenue #1803-4, Chicago, IL 60616
MLS# 12544810Listed by: CHICAGO REALTY PARTNERS, LTD
$131,900Pending2 beds 2 baths1,500 sq. ft.601 E 32nd Street #400, Chicago, IL 60616
MLS# 12524217Listed by: TAYLOR REALTY GROUP LLC
$360,000Active0 Acres3630 S Giles Avenue, Chicago, IL 60653
MLS# 12519863Listed by: RE/MAX 10
$230,000Active0 Acres3529 S Prairie Avenue, Chicago, IL 60653
MLS# 12519919Listed by: RE/MAX 10
$30,000Active0 Acres2545 S Dearborn Street #P-56, Chicago, IL 60616
MLS# 12480797Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$30,000Active0 Acres2545 S Dearborn Street #P-91, Chicago, IL 60616
MLS# 12481608Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$90,000Active0 Acres3333 S Indiana Avenue, Chicago, IL 60616
MLS# 12466069Listed by: COLDWELL BANKER REALTY- Open Sat, 10am to 12pm
$899,000Active4 beds 4 baths3249 S Calumet Avenue, Chicago, IL 60616
MLS# 12451617Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE 
$195,000Active3 beds 2 baths1,700 sq. ft.601 E 32nd Street #801, Chicago, IL 60616
MLS# 12430784Listed by: BETTER HOMES FOR AMERICA, LLC
$165,000Active2 beds 2 baths2605 S Indiana Avenue #2201, Chicago, IL 60616
MLS# 12584740Listed by: BAIRD & WARNER
$129,900Pending3 beds 3 baths1,000 sq. ft.3041 S Michigan Avenue #506, Chicago, IL 60616
MLS# 12367249Listed by: REALTY SERVICES CONSORTIUM
$549,000Pending3 beds 3 baths2,563 sq. ft.3330 S Indiana Avenue #2S, Chicago, IL 60616
MLS# 12574504Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$69,900Active0.08 Acres19 E 37th Place, Chicago, IL 60653
MLS# 12552242Listed by: BAIRD & WARNER
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Copyright 2026 Midwest Real Estate Data LLC. All rights reserved. The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of the Midwest Real Estate Data LLC. Listing information is deemed reliable but not guaranteed.
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© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.