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Douglas, Chicago, IL - homes for sale
81 of 81 results displayed
- New
$200,000Active2 beds 2 baths1,200 sq. ft.3100 S King Drive #602, Chicago, IL 60616
MLS# 12785885Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$997,000Pending4 beds 4 baths3,000 sq. ft.3245 S Calumet Avenue, Chicago, IL 60616
MLS# 12794098Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE- Open Sun, 12 to 2pmNew
$439,500Active2 beds 2 baths1,528 sq. ft.2545 S Dearborn Street #525, Chicago, IL 60616
MLS# 12793562Listed by: COMPASS - Open Fri, 12 to 1:30pmNew
$299,000Active2 beds 2 baths1,133 sq. ft.2545 S Dearborn Street #405, Chicago, IL 60616
MLS# 12792556Listed by: JAMESON SOTHEBY'S INTL REALTY - New
$1,500Active0 Acres50 E 26th Street #PU-61, Chicago, IL 60616
MLS# 12793121Listed by: AVENUE 1 REALTY GROUP 
$140,000Active1 beds 1 baths836 sq. ft.2605 S Indiana Avenue #1007, Chicago, IL 60616
MLS# 12778978Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE- New
$115,000Active1 beds 1 baths2901 S Michigan Avenue #1809, Chicago, IL 60616
MLS# 12790091Listed by: CHI REAL ESTATE GROUP LLC - New
$399,900Active3 beds 2 baths1,450 sq. ft.328 E 25th Place #3W, Chicago, IL 60616
MLS# 12789481Listed by: REALCOM REALTY, LTD 
$130,000Pending1 beds 1 baths870 sq. ft.2901 S Michigan Avenue #405, Chicago, IL 60616
MLS# 12778986Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE- Open Sat, 12 to 2pm
$550,000Active4 beds 4 baths2,560 sq. ft.3839 S Giles Avenue, Chicago, IL 60653
MLS# 12754286Listed by: COLDWELL BANKER REALTY 
$225,000Pending4 beds 3 baths2,100 sq. ft.601 E 32nd Street #310, Chicago, IL 60616
MLS# 12786785Listed by: SUITE 527 REALTY GROUP, LLC
$249,900Pending4 beds 2 baths1,773 sq. ft.3824 S Calumet Avenue, Chicago, IL 60653
MLS# 12778653Listed by: O W AUCTION GROUP LLC
$85,000Active0.07 Acres3714 S Wabash Avenue, Chicago, IL 60653
MLS# 12785714Listed by: ANDRE COLLINS
$225,000Active4 beds 3 baths3645 S Indiana Avenue, Chicago, IL 60653
MLS# 12784936Listed by: RE/MAX PREMIER
$124,900Active1 beds 1 baths700 sq. ft.2605 S Indiana Avenue #304, Chicago, IL 60616
MLS# 12784227Listed by: PAK HOME REALTY
$995,000Active5 beds 4 baths3,000 sq. ft.3319 S Prairie Avenue, Chicago, IL 60616
MLS# 12622017Listed by: COMPASS
$104,900Active-- beds 1 baths650 sq. ft.2901 S Michigan Avenue #308, Chicago, IL 60616
MLS# 12780609Listed by: REALTY OF AMERICA, LLC
$79,000Active0 Acres3343 S Prairie Avenue, Chicago, IL 60616
MLS# 12775300Listed by: MOVIN REALTY INC.
$129,000Active1 beds 1 baths750 sq. ft.2921 S Michigan Avenue #517, Chicago, IL 60616
MLS# 12773315Listed by: COLDWELL BANKER REALTY
$165,000Active1 beds 1 baths900 sq. ft.3021 S Michigan Avenue #407, Chicago, IL 60616
MLS# 12776581Listed by: CENTURY 21 CIRCLE
$119,000Active1 beds 1 baths800 sq. ft.3001 S Michigan Avenue #2105, Chicago, IL 60616
MLS# 12778303Listed by: BAIRD & WARNER
$150,000Active1 beds 1 baths695 sq. ft.345 E Eastgate Place #604, Chicago, IL 60616
MLS# 12773683Listed by: BEST CHICAGO PROPERTIES, LLC
$120,000Active1 beds 1 baths800 sq. ft.3001 S Michigan Avenue #809, Chicago, IL 60616
MLS# 12780469Listed by: SERHANT.
$150,000Active2 beds 2 baths1,100 sq. ft.3021 S Michigan Avenue #306, Chicago, IL 60616
MLS# 12774258Listed by: AIHOME REALTY GROUP LLC
$1,349,000Active5 beds 4 baths4,500 sq. ft.204 E 32nd Street, Chicago, IL 60616
MLS# 12714208Listed by: COMPASS
$489,900Active3 beds 3 baths2,109 sq. ft.3343 S Michigan Avenue, Chicago, IL 60616
MLS# 12773182Listed by: EXP REALTY
$75,000Active0 Acres3635 S Giles Avenue, Chicago, IL 60653
MLS# 12772699Listed by: EJC REAL ESTATE SERVICES
$325,000Active4 beds 3 baths2,355 sq. ft.601 E 32nd Street #610, Chicago, IL 60616
MLS# 12741540Listed by: BERKSHIRE HATHAWAY HOMESERVICES STARCK REAL ESTATE
$230,000Active2 beds 1 baths780 sq. ft.3506 S State Street #312, Chicago, IL 60616
MLS# 12765942Listed by: YOUMU VENTURES LLC
$125,000Pending1 beds 1 baths900 sq. ft.3021 S Michigan Avenue #510, Chicago, IL 60616
MLS# 12764580Listed by: FROG CITY REALTY LLC
$202,000Pending2 beds 2 baths1,165 sq. ft.3100 S King Drive #601, Chicago, IL 60616
MLS# 12764217Listed by: REALTY OF AMERICA, LLC
$486,000Active3 beds 3 baths1,815 sq. ft.3560 S Federal Street, Chicago, IL 60609
MLS# 12763358Listed by: CENTURY 21 REALTY ASSOCIATES
$449,000Active3 beds 3 baths2,033 sq. ft.3541 S Prairie Avenue #4, Chicago, IL 60653
MLS# 12762308Listed by: REAL PEOPLE REALTY
$102,120Pending2 beds 1 baths1,200 sq. ft.601 E 32nd Street #407, Chicago, IL 60616
MLS# 12762680Listed by: PARKVUE REALTY CORPORATION
$430,000Active2 beds 2 baths1,132 sq. ft.2545 S Dearborn Street #533, Chicago, IL 60616
MLS# 12760133Listed by: REDFIN CORPORATION
$484,000Active3 beds 4 baths2,400 sq. ft.3544 S Federal Street, Chicago, IL 60609
MLS# 12734398Listed by: CONCENTRIC REALTY, INC
$250,000Pending6 beds 2 baths2,204 sq. ft.3549 S Indiana Avenue, Chicago, IL 60653
MLS# 12759576Listed by: ERA PARTNERS
$399,000Active2 beds 2 baths1,250 sq. ft.2545 S Dearborn Street #608, Chicago, IL 60616
MLS# 12755533Listed by: BERKSHIRE HATHAWAY HOMESERVICES CHICAGO
$149,000Active1 beds 1 baths759 sq. ft.2605 S Indiana Avenue #2304, Chicago, IL 60616
MLS# 12744601Listed by: LUXE GROUP REAL ESTATE
$145,000Active1 beds 1 baths760 sq. ft.2605 S Indiana Avenue #1507, Chicago, IL 60616
MLS# 12751636Listed by: REAL PEOPLE REALTY
$399,000Active2 beds 3 baths3143 S Michigan Avenue, Chicago, IL 60616
MLS# 12750775Listed by: CENTURY 21 S.G.R., INC.
$225,000Active2 beds 1 baths800 sq. ft.345 E Eastgate Place #302, Chicago, IL 60616
MLS# 12749724Listed by: REALTY OF AMERICA
$275,000Active2 beds 2 baths1,300 sq. ft.3535 S Prairie Avenue #2N, Chicago, IL 60653
MLS# 12744178Listed by: COMPASS
$399,900Active4 beds 3 baths2,330 sq. ft.2731 S Michigan Avenue, Chicago, IL 60616
MLS# 12745333Listed by: RE/MAX SUBURBAN
$115,000Active1 beds 1 baths750 sq. ft.3001 S Michigan Avenue #1303, Chicago, IL 60616
MLS# 12744091Listed by: HOMETOWN REAL ESTATE GROUP LLC
$335,000Active3 beds 2 baths1,500 sq. ft.3745 S Michigan Avenue #2, Chicago, IL 60653
MLS# 12736911Listed by: HOMESMART REALTY GROUP
$119,900Active1 beds 1 baths800 sq. ft.2901 S Michigan Avenue #1704, Chicago, IL 60616
MLS# 12736538Listed by: NEWLIFE REALTY LLC
$117,900Active-- beds 1 baths513 sq. ft.3001 S Michigan Avenue #2406, Chicago, IL 60616
MLS# 12727710Listed by: PEARSON REALTY GROUP
$99,900Active0.08 Acres3821 S State Street, Chicago, IL 60609
MLS# 12724367Listed by: CITY SUBURBAN REAL ESTATE OF IL, INC.
$599,900Active0.41 Acres3739 S State Street, Chicago, IL 60609
MLS# 12724355Listed by: CITY SUBURBAN REAL ESTATE OF IL, INC.
$289,000Pending2 beds 2 baths1,188 sq. ft.347 E 25th Place #2E, Chicago, IL 60616
MLS# 12711997Listed by: RICHLAND PROPERTIES AND HOMES
$140,000Pending1 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
$95,000Pending-- beds 1 baths500 sq. ft.2901 S Michigan Avenue #403, Chicago, IL 60616
MLS# 12698008Listed by: ELLISON PARKER REALTY
$127,000Pending2 beds 2 baths1,038 sq. ft.606 E Woodland Park Avenue #306, Chicago, IL 60616
MLS# 12692886Listed 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
$309,900Active6 beds 4 baths3736 S Calumet Avenue, Chicago, IL 60653
MLS# 12674388Listed by: PEARSON REALTY GROUP
$429,000Pending6 beds 2 baths3,389 sq. ft.3633 S Giles Avenue, Chicago, IL 60653
MLS# 12669141Listed by: COMPASS
$289,000Pending2 beds 2 baths1,136 sq. ft.3506 S State Street #303, Chicago, IL 60609
MLS# 12653021Listed by: CENTURY 21 REALTY ASSOCIATES
$128,650Active-- beds 1 baths420 sq. ft.601 E 32nd Street #403, Chicago, IL 60616
MLS# 12668825Listed by: LUXESQUIRE REALTY
$169,900Pending2 beds 2 baths1,500 sq. ft.25 E 26th Street, Chicago, IL 60616
MLS# 12667653Listed by: HOMES REALTY OF CHICAGO INC
$70,560Pending1 beds 1 baths800 sq. ft.606 E Woodland Avenue #211, Chicago, IL 60616
MLS# 12657841Listed by: PARKVUE REALTY CORPORATION
$249,000Active2 beds 1 baths1,020 sq. ft.3506 S State Street #308, Chicago, IL 60609
MLS# 12652714Listed by: CENTURY 21 REALTY ASSOCIATES
$112,900Active-- beds 1 baths460 sq. ft.3021 S Michigan Avenue #311, Chicago, IL 60616
MLS# 12618386Listed by: INFINITI PROPERTIES, INC.- $79,000Active0 Acres
24 E 37th Place, Chicago, IL 60653
MLS# 12637869Listed by: STARWOOD REAL ESTATE LLC 
$579,000Active2 beds 3 baths2,185 sq. ft.350 E Eastgate Place, Chicago, IL 60616
MLS# 12619160Listed by: CENTURY 21 CIRCLE
$160,000Active1 beds 1 baths760 sq. ft.2605 S Indiana Avenue #1008, Chicago, IL 60616
MLS# 12613517Listed by: COMPASS
$109,900Active0.05 Acres310 E Pershing Road, Chicago, IL 60653
MLS# 12593016Listed by: NELLY CORP REALTY
$389,900Pending6 beds 3 baths3,230 sq. ft.3143 S Giles Avenue, Chicago, IL 60616
MLS# 12591764Listed by: PARKVUE REALTY CORPORATION- $155,000Active0 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
$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
$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
$90,000Active0 Acres3333 S Indiana Avenue, Chicago, IL 60616
MLS# 12466069Listed by: COLDWELL BANKER REALTY
$899,000Active4 beds 4 baths3249 S Calumet Avenue, Chicago, IL 60616
MLS# 12451617Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$89,900Active3 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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©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.