Oakland, Chicago Real Estate & Homes For Sale

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Real Estate & Homes For Sale Near Oakland, Chicago, IL

We found 30 more homes matching your filters just outside Oakland

Oakland, Chicago, IL Real Estate Trends

Learn about the Oakland, Chicago, IL housing market through trends and averages.

Affordability of Living in Oakland, Chicago, IL

The median home value is $395,214
MonthMedian home value
September 2025$391k
October 2025$391k
November 2025$392k
December 2025$395k
January 2026$399k
February 2026$404k
March 2026$409k
April 2026$409k
May 2026$405k
June 2026$399k
July 2026$396k
August 2026$395k
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Trends and affordability stats are provided by third party data sources.

Average Home Value in Oakland, Chicago, IL, by Home Size

Home SizeHome Value*
3 bedrooms (See homes)$391,597
4 bedrooms (See homes)$531,572
*Home value over the past month

Explore the Neighborhood

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Neighborhood stats provided by third party data sources.

What Locals Say about Oakland

  • Trulia User
    Oakland, Chicago
    "The neighborhood is nice everyone knows each other and it’s so many different places to eat at and shop at. I’ve been here for 20 plus years and don’t want to leave"
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  • Trulia User
    Oakland, Chicago
    "I love how friendly the neighbors are everyone speaks to one another and greet one another. People don’t touch other’s packages and the kids are able to play outside with out getting hurt. It’s a quiet neighborhood and I do not want to move away from the area because I enjoy it so much "
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  • Trulia User
    Oakland, Chicago
    "I’ve lived here for 20 years and it has actually gotten better. The crime rate has decreased drastically. "
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  • Trulia User
    Oakland, Chicago
    "the neighborhood is excellent. I've been living here for years and I love the area. There's grocery stores, parks, a lake, and even friendly neighbors. "
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  • Trulia User
    Oakland, Chicago
    "The history of this neighborhood itself is unique. Famous people was born and raised in the neighborhood which was once called the Ida B Wells. "
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  • Ru L
    Oakland, Chicago
    "Bronzeville is a very under the radar community. It’s history is rich and the people here are her kid and neighborly. No neighborhood matches the food, the sincerity, or the architecture. "
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  • Trulia User
    Oakland, Chicago
    "Everybody come to agreement to work to keep companyThe kids community clean and better entertainment for other business"
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  • Medusa C.
    Oakland, Chicago
    "There are parks, librarys, a track, and great schools. You can get anywhere in the city using public transportation. "
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  • Sromanitiah
    Oakland, Chicago
    "close to the beach and not far from restuarants, good schools and convenient to public transportation "
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  • Epj
    Oakland, Chicago
    "Only fifteen minutes by train or ten minutes by car, it’s an easy commute to downtown and to most places just north of downtown."
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  • Rita R.
    Oakland, Chicago
    "Dont know just visiting. So i wouldn't know how dog owner will feel about Oakland area. Its a beautiful place to live and visit."
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  • Shaya f.
    Oakland, Chicago
    "Neighbor is nice and quite, safe and lots of things close by beach, park,ect I love this neighborhood."
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  • Kenny S.
    Oakland, Chicago
    "It’s quiet. Minor issues and there is neighborhood investment. Lakefront is nearby and the 35th bridge is nice to look at."
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  • Orenichiibuuz
    Oakland, Chicago
    "Everything. Lakefront, shopping, transportation, theater, sports, family events around the city neighborhoods. You name it, art fairs, museums. The list goes on."
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  • Candicemathers
    Oakland, Chicago
    "Okay this area is great if you work downtown and want the feel of living in a quiet suburb. The only place to live is on Drexel Blvd. The park across the street is great if you are a dog person. But its important to pick the right blocks. From 43rd street up to the fountain and track-that is for the most part condo owners and sfh owners-not rental units so that is the best area of the ENTIRE BLVD. Also so easy to get to 55, I90/94 and LSD and the city from here. Lots of city workers live down here, teachers and some federal workers are in our condo building as well as people who work for U of Chicago hospital and university. The crime is far more south and west of cottage grove. I don't see it in our neighborhood. If you have kids in the neighborhood, you send them to the Catholic school around the corner. Or the Chicago lab school. I would never send my kids to CPS schools. My neighbor's little girl goes to a school where you have to test into over in Dearborn park which is close. There are also charter schools in the neighborhood. The neighborhood has a long way to go in terms of restaurants and walkability. We have lived here for 9 years and are dog oriented and really like it because of that. Its not dog crowded and people are social in the park. Pitbulls are welcome and dogs of all sizes must be leashed and you gotta pick up. This is a car neighborhood. There is a whole foods coming around 6 blocks away in about a year -we go to roosevelt for all things grocery so this has never bothered me and we go to Medici and restaurants on 53rd to eat often. Its coming along. I'm not a hyde park fan. Its too crowded to park on the street and not car friendly and I'm a car lover-hate public transportation. But many in my building do walk a block over to take the bus to work. You get a lot of space for your money down here. That is the main reason why people move here. You have a family and work in the city and can't afford suburban ridiculous property taxes-"
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Learn more about Oakland

See information on schools, amenities and more.See Oakland Insights
Based on information submitted to the MLS GRID as of 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. 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. Click here for more information