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Woodlawn Real Estate

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Woodlawn Real Estate

Welcome to Woodlawn, a vibrant neighborhood nestled on the South Side of Chicago, Illinois. Known for its rich history and diverse community, Woodlawn is an area that beautifully blends the charm of its past with the excitement of ongoing development. Once home to notable figures such as the legendary civil rights leader, Jesse Jackson, Woodlawn boasts a legacy of resilience and cultural significance.

As you stroll through the tree-lined streets, you'll encounter a mix of architectural styles, from historic greystones to modern townhomes, reflecting the neighborhood's evolution over the years. Woodlawn is not just a place to live; it’s a community that fosters a strong sense of belonging. The neighborhood is home to a variety of local businesses, cafes, and parks that encourage residents to connect and engage with one another.

One of the standout features of Woodlawn is its proximity to the University of Chicago, making it an ideal location for students, faculty, and families alike. The neighborhood is also undergoing a renaissance, with new developments bringing fresh energy and amenities to the area, including the upcoming Woodlawn Commons, which promises to enhance the local landscape.

Outdoor enthusiasts will appreciate the expansive Washington Park, offering ample green space for recreation, picnics, and community events. With its rich cultural heritage, thriving community spirit, and convenient access to public transportation, Woodlawn is a neighborhood that invites you to explore, engage, and call it home. Discover the unique charm of Woodlawn, where history meets opportunity in the heart of Chicago!

Newest Listings in Woodlawn

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
  • ACTIVE 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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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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6642 S Drexel Avenue, Chicago image
6642 S Drexel Avenue, Chicago $559,000

Welcome to 6642 S. Drexel Avenue, a beautifully restored historic residence in the heart of Woodlawn that has been thoughtfully deconverted from a two-flat into a stunnin...

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  • 3 Beds
  • 5 Baths
  • 12746791 MLS
  • ACTIVE Status
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6231 S Woodlawn Avenue Unit #3N, Chicago image
6231 S Woodlawn Avenue Unit #3N, Chicago $295,000 ▼

Welcome to the heart of New Woodlawn! This spacious 3-bedroom, 2-bath condominium offers the perfect blend of comfort, style, and location in one of Chicago's most dynami...

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  • 3 Beds
  • 2 Baths
  • 12743966 MLS
  • ACTIVE Status
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6103 S Kimbark Avenue Unit #3E, Chicago image
6103 S Kimbark Avenue Unit #3E, Chicago $210,000

Welcome to this charming condo nestled in the highly desirable Woodlawn neighborhood. This top-floor 2-bedroom condo offers abundant natural light and the added privacy a...

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  • 2 Beds
  • 1 Baths
  • 12744751 MLS
  • ACTIVE Status
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5451 N. Ludlam Ave. Chicago IL. 60630
+18473380806
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