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Our website features the best Woodlawn real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Hot Woodlawn Properties

6627 S Maryland Avenue, Chicago image
6627 S Maryland Avenue, Chicago $849,000

Legal 3 fla.Total gut Rehab to the studs with new constructions permits, all mechanicals are brand new. New water lines B Box and meters, windows, insulations, GE applian...

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  • 7 Beds
  • 6 Baths
  • 12755888 MLS
  • NEW Status
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6526 S Kimbark Avenue Unit #2S, Chicago image
6526 S Kimbark Avenue Unit #2S, Chicago $290,000

Spacious and beautifully appointed 3-bedroom, 2-bath condominium offering approximately 1,700 square feet of comfortable living space in a highly desirable location. Thi...

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  • 3 Beds
  • 2 Baths
  • 12754115 MLS
  • NEW Status
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6511 S Ellis Avenue, Chicago image
6511 S Ellis Avenue, Chicago $267,000

Welcome to 6511 S Ellis Ave, an updated 4-bedroom, 1.5-bath townhome offering generous living area and plenty of outdoor space. Updates include new flooring, kitchen back...

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  • 4 Beds
  • 2 Baths
  • 12744188 MLS
  • ACTIVE Status
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6324 S Kimbark Avenue Unit #300, Chicago image
6324 S Kimbark Avenue Unit #300, Chicago $240,000

Cultural Legacy Meets Lakeside Luxury | Turn-Key Hyde Park/Woodlawn Oasis. Welcome to Kimbark Estates; a striking, classic brick icon offering the definitive Chicago life...

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  • 2 Beds
  • 2 Baths
  • 12751538 MLS
  • ACTIVE Status
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6216 S Woodlawn Avenue Unit #B, Chicago image
6216 S Woodlawn Avenue Unit #B, Chicago $759,000

Discover INSPIRE Woodlawn, a gated community of 14 newly constructed townhomes designed by Studio Dwell Architects. These extra-wide 27' residences are thoughtfully craft...

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  • 3 Beds
  • 3 Baths
  • 12751241 MLS
  • ACTIVE Status
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6611 S Maryland Avenue, Chicago image
6611 S Maryland Avenue, Chicago $419,900

Smart buy, attainably priced! Cool & dramatic, First floor three bedroom, one bath apartment with hardwood floors throughout, a modern kitchen, beautiful bath and hookup...

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  • 6 Beds
  • 2 Baths
  • 12750297 MLS
  • ACTIVE Status
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15644 N Sunfish Lane, Woodlawn image
15644 N Sunfish Lane, Woodlawn $299,000

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  • 4 Beds
  • 2 Baths
  • 12749255 MLS
  • ACTIVE Status
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6109 S Greenwood Avenue, Chicago image
6109 S Greenwood Avenue, Chicago $1,198,988

This beautiful, rare, and meticulously maintained vintage greystone is a fantastic, solid investment opportunity and an investor's dream! An ideal turnkey operation, it f...

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  • 8 Beds
  • 4 Baths
  • 12749117 MLS
  • ACTIVE Status
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6508 S Ingleside Avenue, Chicago image
6508 S Ingleside Avenue, Chicago $930,000

Introducing a stunning newer construction 3-unit building in the heart of Woodlawn-an exceptional, income-producing investment opportunity in one of Chicago's most rapidl...

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  • 9 Beds
  • 6 Baths
  • 12747729 MLS
  • ACTIVE Status
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6638 S Woodlawn Avenue, Chicago image
6638 S Woodlawn Avenue, Chicago $1,200,000

Turnkey cash flowing Rarely Available 4 Flat Building Located in prime East Woodlawn desirable community just steps from Obama Presidential Library, University of Chicago...

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  • 11 Beds
  • 7 Baths
  • 12726785 MLS
  • ACTIVE Status
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The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED 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.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.

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