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Douglas, Chicago, IL - homes for sale
76 of 76 results displayed
- New
$399,000Active2 beds 2 baths1,250 sq. ft.2545 S Dearborn Street #608, Chicago, IL 60616
MLS# 12755533Listed by: BERKSHIRE HATHAWAY HOMESERVICES CHICAGO
- New
$140,000Active1 beds 1 baths836 sq. ft.2605 S Indiana Avenue #1007, Chicago, IL 60616
MLS# 12754202Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE - New
$124,900Active1 beds 1 baths800 sq. ft.3001 S Michigan Avenue #2105, Chicago, IL 60616
MLS# 12755040Listed by: BAIRD & WARNER - New
$169,000Active1 beds 1 baths759 sq. ft.2605 S Indiana Avenue #2304, Chicago, IL 60616
MLS# 12744601Listed by: LUXE GROUP REAL ESTATE - New
$135,000Active1 beds 1 baths870 sq. ft.2901 S Michigan Avenue #405, Chicago, IL 60616
MLS# 12754210Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE - New
$475,000Active2 beds 2 baths1,528 sq. ft.2545 S Dearborn Street #525, Chicago, IL 60616
MLS# 12754159Listed by: COMPASS - New
$530,000Active3 beds 2 baths2,674 sq. ft.3330 S Indiana Avenue #2N, Chicago, IL 60616
MLS# 12753255Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE - New
$145,000Active1 beds 1 baths760 sq. ft.2605 S Indiana Avenue #1507, Chicago, IL 60616
MLS# 12751636Listed by: REAL PEOPLE REALTY - New
$399,000Active2 beds 3 baths3143 S Michigan Avenue, Chicago, IL 60616
MLS# 12750775Listed by: CENTURY 21 S.G.R., INC. - Open Sat, 12 to 2pmNew
$479,000Active3 beds 3 baths2,250 sq. ft.3541 S Prairie Avenue #4, Chicago, IL 60653
MLS# 12750168Listed by: REAL PEOPLE REALTY 
$225,000Active2 beds 1 baths800 sq. ft.345 E Eastgate Place #302, Chicago, IL 60616
MLS# 12749724Listed by: REALTY OF AMERICA
$400,000Active2 beds 2 baths1,894 sq. ft.50 E 26th Street #421, Chicago, IL 60616
MLS# 12745472Listed by: COMPASS
$255,000Active2 beds 2 baths1,237 sq. ft.2901 S Michigan Avenue #808-809, Chicago, IL 60616
MLS# 12741814Listed by: KALE REALTY
$275,000Active2 beds 2 baths1,300 sq. ft.Address Withheld By Seller, 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
$130,000Active1 beds 1 baths750 sq. ft.3001 S Michigan Avenue #1303, Chicago, IL 60616
MLS# 12744091Listed by: HOMETOWN REAL ESTATE GROUP LLC
$103,000Pending-- beds 1 baths440 sq. ft.2901 S Michigan Avenue #506, Chicago, IL 60616
MLS# 12740085Listed by: MAGIERA CITY LLC
$314,990Active2 beds 2 baths1,288 sq. ft.318 E 25th Place #2E, Chicago, IL 60616
MLS# 12737139Listed by: JAMESON SOTHEBY'S INTL REALTY
$118,500Active1 beds 1 baths750 sq. ft.2921 S Michigan Avenue #109, Chicago, IL 60616
MLS# 12736347Listed by: CHARLES RUTENBERG REALTY OF IL
$335,000Active2 beds 2 baths1,500 sq. ft.31 E 26th Street #3, Chicago, IL 60616
MLS# 12736225Listed by: CENTURY 21 S.G.R., INC.
$260,000Pending2 beds 1 baths1,000 sq. ft.17 W 35th Street #304, Chicago, IL 60616
MLS# 12738459Listed by: EXP REALTY
$499,900Active3 beds 3 baths2,109 sq. ft.3343 S Michigan Avenue, Chicago, IL 60616
MLS# 12737244Listed by: EXP REALTY
$335,000Active3 beds 2 baths1,500 sq. ft.3745 S Michigan Avenue #2, Chicago, IL 60653
MLS# 12736911Listed by: HOMESMART REALTY GROUP
$123,000Active1 beds 1 baths800 sq. ft.2901 S Michigan Avenue #1704, Chicago, IL 60616
MLS# 12736538Listed by: NEWLIFE REALTY LLC
$139,000Active1 beds 1 baths750 sq. ft.3021 S Michigan Avenue #305, Chicago, IL 60616
MLS# 12704996Listed by: BAIRD & WARNER
$121,500Active-- beds 1 baths513 sq. ft.3001 S Michigan Avenue #2406, Chicago, IL 60616
MLS# 12727710Listed by: PEARSON REALTY GROUP
$138,400Active1 beds 1 baths700 sq. ft.2605 S Indiana Avenue #304, Chicago, IL 60616
MLS# 12727149Listed by: PAK HOME REALTY
$349,999Pending3 beds 2 baths1,700 sq. ft.3565 S King Drive #1, Chicago, IL 60653
MLS# 12722659Listed by: JAMESON SOTHEBY'S INTL REALTY
$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.
$561,800Pending3 beds 4 baths4,558 sq. ft.3126 S Calumet Avenue, Chicago, IL 60616
MLS# 12723877Listed by: REALHOME SERVICES & SOLUTIONS, INC.
$159,900Active2 beds 2 baths1,100 sq. ft.3021 S Michigan Avenue #306, Chicago, IL 60616
MLS# 12722045Listed by: AIHOME REALTY GROUP LLC
$499,999Active2 beds 2 baths2,080 sq. ft.2502 S Calumet Avenue, Chicago, IL 60616
MLS# 12707918Listed by: KALE REALTY
$150,000Active1 beds 1 baths900 sq. ft.3021 S Michigan Avenue #510, Chicago, IL 60616
MLS# 12717033Listed by: FROG CITY REALTY LLC
$195,000Active1 beds 1 baths900 sq. ft.2605 S Indiana Avenue #2205, Chicago, IL 60616
MLS# 12716689Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$425,000Pending4 beds 3 baths2,400 sq. ft.2819 S Michigan Avenue, Chicago, IL 60616
MLS# 12526499Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$125,000Pending1 beds 1 baths800 sq. ft.2901 S Michigan Avenue #1610, Chicago, IL 60616
MLS# 12714851Listed by: KALE REALTY
$289,000Active2 beds 2 baths1,188 sq. ft.347 E 25th Place #2E, Chicago, IL 60616
MLS# 12711997Listed by: RICHLAND PROPERTIES AND HOMES
$275,000Active4 beds 3 baths2,100 sq. ft.601 E 32nd Street #310, Chicago, IL 60616
MLS# 12709629Listed by: SUITE 527 REALTY GROUP, LLC
$140,000Active1 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
$2,500Active0 Acres50 E 26th Street #PU-61, Chicago, IL 60616
MLS# 12705666Listed by: AVENUE 1 REALTY GROUP
$95,000Active-- 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
$475,000Active6 beds 3 baths3,389 sq. ft.3633 S Giles Avenue, Chicago, IL 60653
MLS# 12669141Listed by: COMPASS
$279,000Pending2 beds 2 baths1,136 sq. ft.3506 S State Street #303, Chicago, IL 60609
MLS# 12653021Listed by: CENTURY 21 REALTY ASSOCIATES
$129,000Active-- beds 1 baths420 sq. ft.601 E 32nd Street #403, Chicago, IL 60616
MLS# 12668825Listed by: LUXESQUIRE REALTY
$184,900Active2 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
$259,000Pending2 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.
$219,999Active2 beds 1 baths780 sq. ft.3506 S State Street #312, Chicago, IL 60616
MLS# 12647391Listed by: YOUMU VENTURES LLC
$199,999Pending2 beds 2 baths1,500 sq. ft.601 E 32nd Street #800, Chicago, IL 60616
MLS# 12640596Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$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 
$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
$85,000Pending-- beds 1 baths600 sq. ft.2921 S Michigan Avenue #413, Chicago, IL 60616
MLS# 12597302Listed by: KALE REALTY
$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- $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
$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
$30,000Active0 Acres2545 S Dearborn Street #P-91, Chicago, IL 60616
MLS# 12481608Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$899,000Active4 beds 4 baths3249 S Calumet Avenue, Chicago, IL 60616
MLS# 12451617Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$159,900Pending2 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
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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.