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Real Estate and Neighborhood Information

Woodlawn Overview

This south side Chicago neighborhood is home to an idyllic golf course, two yacht clubs and a lovely public beach. Woodlawn's residents enjoy a community conveniently located near recreational parks, the scenic lakefront, and the bustling University of Chicago campus. The area has all types of real estate where folks from all walks of life happily make their home. Affordable detached houses with private yards and their own garage give families enough room to grow, and condominiums are great properties for students, couples and young families just starting out. A number of schools and academies are situated in Woodlawn, giving homeowners plenty of options for their children's education, without straying too far from home.

103 Woodlawn Homes For Sale

Showing 1 - 20 of 103 View all 103 homes

Woodlawn neighborhood has an array of housing options for Chicagoans—and any re-locaters planning the move to Chicago—everything from inexpensive single-family homes with up to five bedrooms to newfangled condo conversions. It’s hard to resist the allure of affordable condominiums with luxury trimmings like granite countertops, hardwood flooring and stainless steel appliances, but some prefer the cozy comforts of vintage design, hard oak moldings and creaky floorboards. Luckily, Woodlawn neighborhood has all types of real estate where folks from all walks of life happily make their home.

No matter what you are looking for in a living space, Woodlawn’s residential streets are a good place to start your search. Families will be pleased to find plenty of detached homes with their own yard and garage parking, while other homebuyers might love the large condos with individual decks, which have many of the same features as the private homes, without the maintenance.

Woodlawn History

From farmland to fairgrounds to civic protest, the Chicago neighborhood of Woodlawn has seen it all. With a lovely park on the lake and the University of Chicago’s campus to the north, Woodlawn is positioned to enjoy much of Chicago’s advantages. But, it hasn’t all been rosy.

Dutch farmers first settled Woodlawn in the 1850s. The population swelled from 1,000 inhabitants in 1890 to over 20,000 in 1893, the year of the World Columbian Exposition, which was held in Jackson Park, a lakefront location on the eastern part of this Chicago neighborhood. The World’s Fair celebrated 400 years since Columbus landed in America and it was a great boost to Woodlawn’s economy, bringing with it entrepreneurs, artists and a buzz of activity to many neighborhoods in the south side of Chicago.

In the early part of the 20th century, Woodlawn underwent a demographic shift as an influx of African American families to the neighborhood occurred. These families were part of the Great Migration; people leaving the South looking for work in Chicago’s factories and other northern industries. Absentee white landlords with strong racial prejudices didn’t make Woodlawn an easy place to live for African Americans. In fact, the difficult living conditions were dramatized in a play by Lorraine Hansberry, called A Raisin in the Sun. Drawing on her own childhood in Woodlawn, the author described the crowded tenements and her father’s legal battle against unfair standards. A little side note: Starring Sidney Poitier, this was the first play by an African American woman to reach Broadway.

In the late 1950s, Dr. Brazier (now the pastor of Apostolic Church of God in Woodlawn) asked Saul Alinsky (a champion of organized protest) to help Woodlawn residents organize themselves and fight for better living conditions. Collectively they formed the Temporary Woodlawn Organization (or TWO), which protested crowded public schools, slum landlords and fought the University of Chicago’s plan to expand into Woodlawn. They helped bring together many block clubs, churches and other existing groups in hopes to build the neighborhood up as a more powerful force that could effect change in Woodlawn. TWO’s efforts forced landlords to improve and repair their buildings and gave Woodlawn residents the tools to wield more political power through organized demonstrations and civic action. To this day, TWO continues its proud presence in this Chicago neighborhood assisting with senior citizen and public housing, truancy intervention, and substance abuse.

Dream Town Knows Woodlawn

As Chicago neighborhood experts, Dream Town has successfully sold properties in Woodlawn. Dream Town holds a well-earned reputation for its impressive sales volume and dedication to personal, attentive service. Benefit from the Dream Town advantage when selling your Woodlawn home. Utilizing state-of-the-art technology, Dream Town drives more sales than any other Chicago brokerage.

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6346 South GREENWOOD, Chicago IL, 60637 #
Sold For $75,000

The Sights of Woodlawn

Woodlawn Neighborhood Photo
Woodlawn Neighborhood Photo
Woodlawn Neighborhood Photo

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Schools In The Woodlawn Area

See grade levels, address, and scores for schools in the Woodlawn area.

School Type Grade Rating

Dr. Martin Luther King, Jr. Academy of Social Justice

644 West 71st Street - public

Preschool - Middle PK-8

Kenwood Academy High School

5015 South Blackstone Ave - public

Middle - High 7-12

Murray Elementary Language Academy

5335 South Kenwood Ave - public

Elementary - Middle K-8

Ray Elementary School

5631 South Kimbark Avenue - public

Preschool - Elementary PK-7

Revere Elementary School

1010 East 72nd St - public

Preschool - Middle PK-8

Sherwood Elementary School

245 West 57th St - public

Preschool - Middle PK-8

Wadsworth PreK-8th STEM School

6650 S. Ellis Avenue - public

Preschool - Middle PK-5

Beethoven Elementary School

25 West 47th St - public

Preschool - Middle PK-8

Mays Elementary Academy

6656 South Normal Blvd - public

Preschool - Middle PK-8

Dewey Elementary Academy Of Fine Arts

5415 South Union Ave - public

Preschool - Middle PK-8

Fiske Elementary School

6020 South Langley Ave - public

Preschool - Middle PK-8

Parkman Elementary School

245 West 51st St - public

Preschool - Middle PK-8

Sexton Elementary School

6020 South Langley Ave - public

Preschool - Middle PK-8

Mt Carmel High School

6410 South Dante Avenue - private

High 9-12

Ancona School

4770 S Dorchester Ave - private

Preschool - Middle PK-8

Sonia Shankman Orthogenic School

1365 East 60th Street - private

Elementary - High 3-12

Visitation Catholic School

900 West Garfield Boulevard - private

Preschool - Middle PK-8

Amandla Elementary Charter School

6800 South Stewart Ave - charter

Elementary - High 5-10

Love Faith And Praise Academy

6948 South Stewart Avenue - private

Preschool - High PK-12

Sonia Shankman Orthogenic-Day

1365 East 60th Street - private

Elementary - High n/a

School data provided by GreatSchools.School service boundaries are intended to be used as reference only. To verify enrollment eligibility for a property, contact the school directly. GreatSchools Ratings provided by GreatSchools.org.

Surrounding Neighborhoods

Neighbor Photo