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Douglas, Chicago, IL - homes for sale
71 of 71 results displayed
- New
$409,900Active4 beds 3 baths2,330 sq. ft.2731 S Michigan Avenue, Chicago, IL 60616
MLS# 12706826Listed by: RE/MAX SUBURBAN
- Open Sun, 1 to 3pmNew
$499,999Active2 beds 2 baths2,080 sq. ft.2502 S Calumet Avenue, Chicago, IL 60616
MLS# 12707918Listed by: KALE REALTY - Open Sun, 12:15 to 1:45pmNew
$140,000Active1 beds 1 baths870 sq. ft.2901 S Michigan Avenue #405, Chicago, IL 60616
MLS# 12718501Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE - New
$150,000Active1 beds 1 baths900 sq. ft.3021 S Michigan Avenue #510, Chicago, IL 60616
MLS# 12717033Listed by: FROG CITY REALTY LLC - New
$225,000Active1 beds 1 baths900 sq. ft.2605 S Indiana Avenue #2205, Chicago, IL 60616
MLS# 12716689Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE - New
$179,900Active2 beds 2 baths1,325 sq. ft.2605 S Indiana Avenue #402, Chicago, IL 60616
MLS# 12716586Listed by: KELLER WILLIAMS PREFERRED RLTY - New
$425,000Active4 beds 3 baths2,400 sq. ft.2819 S Michigan Avenue, Chicago, IL 60616
MLS# 12526499Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE - New
$549,000Active3 beds 2 baths2,000 sq. ft.2545 S Dearborn Street #702, Chicago, IL 60616
MLS# 12715672Listed by: BERKSHIRE HATHAWAY HOMESERVICES CHICAGO - New
$125,000Active1 beds 1 baths800 sq. ft.2901 S Michigan Avenue #1610, Chicago, IL 60616
MLS# 12714851Listed by: KALE REALTY 
$525,000Pending3 beds 3 baths2,109 sq. ft.3343 S Michigan Avenue, Chicago, IL 60616
MLS# 12710439Listed by: EXP REALTY- New
$299,000Active2 beds 2 baths1,188 sq. ft.347 E 25th Place #2E, Chicago, IL 60616
MLS# 12711997Listed by: RICHLAND PROPERTIES AND HOMES - New
$139,000Active1 beds 1 baths800 sq. ft.3001 S Michigan Avenue #2105, Chicago, IL 60616
MLS# 12706994Listed by: BAIRD & WARNER - Open Sun, 11am to 12:30pmNew
$545,000Active3 beds 2 baths2,674 sq. ft.3330 S Indiana Avenue #2N, Chicago, IL 60616
MLS# 12697638Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE 
$275,000Active4 beds 3 baths2,100 sq. ft.601 E 32nd Street #310, Chicago, IL 60616
MLS# 12709629Listed by: SUITE 527 REALTY GROUP, LLC
$155,000Active1 beds 1 baths760 sq. ft.2605 S Indiana Avenue #1404, Chicago, IL 60616
MLS# 12706305Listed by: CONCENTRIC REALTY INC.
$1,198,000Active9 beds 9 baths3762 S Indiana Avenue, Chicago, IL 60653
MLS# 12706029Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE- Open Sun, 10:30am to 12pm
$145,000Active1 beds 1 baths836 sq. ft.2605 S Indiana Avenue #1007, Chicago, IL 60616
MLS# 12697797Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE 
$699,900Pending9 beds 5 baths3819 S Wabash Avenue, Chicago, IL 60653
MLS# 12697744Listed by: KELLER WILLIAMS ONECHICAGO
$2,500Active0 Acres50 E 26th Street #PU-61, Chicago, IL 60616
MLS# 12705666Listed by: AVENUE 1 REALTY GROUP
$139,900Active1 beds 1 baths700 sq. ft.2605 S Indiana Avenue #304, Chicago, IL 60616
MLS# 12700913Listed by: PAK HOME REALTY
$280,000Active2 beds 1 baths1,000 sq. ft.17 W 35th Street #304, Chicago, IL 60616
MLS# 12701011Listed by: CLOUD GATE REALTY LLC
$95,000Active-- beds 1 baths500 sq. ft.2901 S Michigan Avenue #403, Chicago, IL 60616
MLS# 12698008Listed by: ELLISON PARKER REALTY
$435,000Active2 beds 2 baths2545 S Dearborn Street #530, Chicago, IL 60616
MLS# 12683426Listed by: O W AUCTION GROUP LLC
$127,000Active2 beds 2 baths1,038 sq. ft.606 E Woodland Park Avenue #306, Chicago, IL 60616
MLS# 12692886Listed by: PEARSON REALTY GROUP
$130,000Active-- beds 1 baths513 sq. ft.3001 S Michigan Avenue #2406, Chicago, IL 60616
MLS# 12692230Listed by: PEARSON REALTY GROUP
$114,900Active-- beds 1 baths500 sq. ft.2901 S Michigan Avenue #903, Chicago, IL 60616
MLS# 12690540Listed by: REALTY EXECUTIVES ELITE
$210,000Pending2 beds 2 baths1,000 sq. ft.3001 S Michigan Avenue #2202, Chicago, IL 60616
MLS# 12683998Listed by: BERKSHIRE HATHAWAY HOMESERVICES CHICAGO
$127,500Pending1 beds 1 baths900 sq. ft.2901 S Michigan Avenue #1404, Chicago, IL 60616
MLS# 12679275Listed by: BAIRD & WARNER
$389,000Pending2 beds 2 baths3105 S Giles Avenue #1S, Chicago, IL 60616
MLS# 12682712Listed by: COMPASS
$309,900Pending6 beds 4 baths3736 S Calumet Avenue, Chicago, IL 60653
MLS# 12674388Listed by: PEARSON REALTY GROUP
$168,999Active2 beds 2 baths1,100 sq. ft.3021 S Michigan Avenue #306, Chicago, IL 60616
MLS# 12673594Listed by: AIHOME REALTY GROUP LLC
$549,000Active6 beds 3 baths3,389 sq. ft.3633 S Giles Avenue, Chicago, IL 60653
MLS# 12669141Listed by: COMPASS
$279,000Active2 beds 2 baths1,136 sq. ft.3506 S State Street #303, Chicago, IL 60609
MLS# 12653021Listed by: CENTURY 21 REALTY ASSOCIATES
$99,900Pending0.08 Acres3808 S Wabash Avenue, Chicago, IL 60653
MLS# 12644489Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$134,500Active-- beds 1 baths420 sq. ft.601 E 32nd Street #403, Chicago, IL 60616
MLS# 12668825Listed by: LUXESQUIRE REALTY
$199,900Active2 beds 2 baths1,500 sq. ft.25 E 26th Street, Chicago, IL 60616
MLS# 12667653Listed by: HOMES REALTY OF CHICAGO INC
$230,000Active2 beds 2 baths1,200 sq. ft.3560 S Giles Avenue, Chicago, IL 60653
MLS# 12559822Listed by: ESM REALTY GROUP
$342,000Pending2 beds 2 baths1,288 sq. ft.317 E 25th Street #3E, Chicago, IL 60616
MLS# 12667098Listed by: JAMESON SOTHEBY'S INTL REALTY
$70,560Pending1 beds 1 baths800 sq. ft.606 E Woodland Avenue #211, Chicago, IL 60616
MLS# 12657841Listed by: PARKVUE REALTY CORPORATION
$259,000Active2 beds 1 baths1,020 sq. ft.3506 S State Street #308, Chicago, IL 60609
MLS# 12652714Listed by: CENTURY 21 REALTY ASSOCIATES
$104,000Active-- beds 1 baths440 sq. ft.2901 S Michigan Avenue #506, Chicago, IL 60616
MLS# 12651479Listed by: MAGIERA CITY LLC
$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
$199,999Active2 beds 2 baths1,500 sq. ft.601 E 32nd Street #800, Chicago, IL 60616
MLS# 12640596Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$484,000Pending3 beds 3 baths2,469 sq. ft.3560 S Federal Street, Chicago, IL 60609
MLS# 12643445Listed by: CENTURY 21 REALTY ASSOCIATES
$294,999Active2 beds 2 baths1,500 sq. ft.19 E 26th Street #1, Chicago, IL 60616
MLS# 12640751Listed by: BEYCOME BROKERAGE REALTY LLC- $79,000Active0 Acres
24 E 37th Place, Chicago, IL 60653
MLS# 12637869Listed by: STARWOOD REAL ESTATE LLC 
$136,500Active1 beds 1 baths727 sq. ft.2605 S Indiana Avenue #1208, Chicago, IL 60616
MLS# 12636667Listed by: DARKO TESANOVIC
$579,000Active2 beds 3 baths2,185 sq. ft.350 E Eastgate Place, Chicago, IL 60616
MLS# 12619160Listed by: CENTURY 21 CIRCLE
$165,000Pending2 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
$90,000Active-- beds 1 baths600 sq. ft.2921 S Michigan Avenue #413, Chicago, IL 60616
MLS# 12597302Listed by: KALE REALTY
$200,000Pending3 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- $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
$330,000Pending6 beds 2 baths2,204 sq. ft.3549 S Indiana Avenue, Chicago, IL 60653
MLS# 12581786Listed by: ERA PARTNERS
$1,200,000Active8 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
$150,000Pending1 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
$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 
$190,000Pending3 beds 2 baths1,700 sq. ft.601 E 32nd Street #801, Chicago, IL 60616
MLS# 12430784Listed by: BETTER HOMES FOR AMERICA, LLC
$159,900Active2 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
$69,900Active0.08 Acres19 E 37th Place, Chicago, IL 60653
MLS# 12552242Listed by: BAIRD & WARNER
Local realty services provided by:CENTURY 21 Affiliated
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. MLSNI Member Broker: David Try
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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 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.
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 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.