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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

6621 S Drexel Avenue, Chicago image
6621 S Drexel Avenue, Chicago $980,000

Welcome to this exceptional 3-flat multi-unit property with a 3-car detached garage, located in the desirable Woodlawn neighborhood, just minutes from the University of C...

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  • 9 Beds
  • 6 Baths
  • 12626647 MLS
  • NEW Status
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6534 S Kimbark Avenue Unit #3, Chicago image
6534 S Kimbark Avenue Unit #3, Chicago $289,000

Welcome home to this sun-drenched 3-bedroom, 2-bath condo perched on the top floor of a brick walk-up in the heart of Woodlawn. Freshly painted throughout in timeless Whi...

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  • 3 Beds
  • 2 Baths
  • 12718928 MLS
  • NEW Status
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6505 S Woodlawn Avenue, Chicago image
6505 S Woodlawn Avenue, Chicago $599,000

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  • 4 Beds
  • 3 Baths
  • 12717623 MLS
  • NEW Status
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6500 S Minerva Avenue Unit #3N, Chicago image
6500 S Minerva Avenue Unit #3N, Chicago $289,999

Discover urban elegance in the heart of the highly desirable Woodlawn neighborhood with this beautifully renovated 2-bedroom, 2-bathroom condo. This meticulously updated ...

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  • 2 Beds
  • 2 Baths
  • 12716557 MLS
  • NEW Status
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6651 S Drexel Avenue Unit #1E, Chicago image
6651 S Drexel Avenue Unit #1E, Chicago $299,800

Beautifully Renovated 3-Bedroom, 3-Bath Duplex Condo with Private Entrance Experience the comfort of townhome-style living in this beautifully renovated duplex condomi...

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  • 3 Beds
  • 3 Baths
  • 12711975 MLS
  • ACTIVE Status
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6506 S Ingleside Avenue, Chicago image
6506 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
  • 12712761 MLS
  • ACTIVE Status
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1506 E Marquette Road, Chicago image
1506 E Marquette Road, Chicago $600,000

Welcome to 1506 E. Marquette Rd., Chicago, IL, a beautifully designed home offering the perfect combination of space, comfort, and modern living. This spacious residence ...

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  • 4 Beds
  • 4 Baths
  • 12696617 MLS
  • ACTIVE 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
  • 12710724 MLS
  • ACTIVE Status
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6520 S Ellis Avenue, Chicago image
6520 S Ellis Avenue, Chicago $519,000 ▼

Move right into this beautifully updated East Woodlawn two-unit offering the perfect blend of immediate income potential and comfortable owner-occupancy. The spacious fir...

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  • 7 Beds
  • 3 Baths
  • 12710583 MLS
  • PRICE CHANGE Status
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6538 S Kimbark Avenue, Chicago image
6538 S Kimbark Avenue, Chicago $699,000

New construction single-family home in Woodlawn featuring 3 bedrooms and 2.5 baths. Open-concept main level with spacious living room, dining area, and a modern kitchen w...

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  • 3 Beds
  • 3 Baths
  • 12706953 MLS
  • ACTIVE Status
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1009 E 61St Street, Chicago image
1009 E 61St Street, Chicago $469,000

Stunning townhome located right next to the University of Chicago campus, directly across the street from the dorms. This tri-level home features an open-concept main lev...

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  • 3 Beds
  • 2 Baths
  • 12706715 MLS
  • ACTIVE Status
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6108 S Kimbark Avenue Unit #2E, Chicago image
6108 S Kimbark Avenue Unit #2E, Chicago $199,500

Welcome to this charming, vintage courtyard co-op. This freshly painted 3-bedroom, 1-bath co-op is filled with natural light and offers a spacious open-concept living an...

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  • 3 Beds
  • 1 Baths
  • 12686271 MLS
  • ACTIVE Status
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