$440,887Average Value$195Average Price per Sq Ft7Homes For Sale
Oakland is all about historic homes and lakeside parks
Oakland is a South Side Chicago neighborhood full of beautiful historic architecture and plenty of green spaces. Lake Shore Drive sits between the community and Lake Michigan, where Burnham Park has plenty of things to do by the water. Beyond the historic buildings, monuments and plaques throughout parks share the area’s local history and culture, keeping it alive even as new construction and residents come in.
Oakland offers wonderful views and close proximity to downtown Chicago.
Oakland is a lakefront Chicago neighborhood with scenic skyline views, amenities and culture.
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Oakland's beach and community green spaces
Burnham Park is the largest of Oakland’s green spaces. Oakwood Beach is here, with lifeguards in the summer. The playground, skatepark and basketball courts also overlook the water. Lakefront Trail goes through here, offering paved pedestrian and bike lanes that go along Chicago’s coast. Ellis Park also has a playground and basketball courts. The Arts and Recreation Center at Ellis Park has an indoor pool and gym, as well as a rooftop terrace. The Light of Truth Ida B. Well National Monument is also here, honoring the woman and the housing units named after her that were torn down in the early 2000s. Mandrake Park has a long greenway where lots of people go to walk around. “It’s also where everyone goes for kids’ club sports since they host their games over there,” says Realtor Shaena Flanagan with Coldwell Banker Realty and Oakland resident. The park has a turf field and basketball, tennis and pickleball courts.
Summer is well spent on the sandy shores of Oakwood Beach.
Skaters hit a front-side wall ride at Burnham Skate Park just north of Oakland.
As the sun sets, a biker races home along Oakland's Lakefront Trail.
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Historic Victorians alongside newer condos and townhomes
Oakland is known for its selection of Victorian homes with turrets and intricate designs. “When you travel down Drexel Avenue, you see all kinds of buildings. They’re all pretty large and they’re all structurally beautiful,” says broker Tamika Marks with Trademarks and Associates. Iron gates separate sidewalks from front walkways. Recent developments in the early 2000s have also increased the number of mid-rise condos and brick townhomes, making them the most common housing option here. Wide streets mean there’s plenty of room for street parking, but most homes have detached garages behind properties.
Oakland features unique homes from the 1800's.
Condo buildings with mature trees make up the main bulk of Oakland's available housing.
Brick two-flat homes built in the early 1970s come with gated front yards in Oakland.
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Oakland is more expensive than other South Side neighborhoods
Compared to the surrounding areas, Oakland is more expensive. Oakland’s median housing price is about $350,000, which is higher than Bronzeville and Lake Meadows and almost double Kenwood's median. Condos and townhomes typically range from the lower $200,000s to upper $300,000s, while single-family homes range from the low $500,000s to the low $800,000s, though they are slower to come on the market.
Historic schools and charters through the University of Chicago
Oakland is part of Chicago Public Schools. It’s a school choice district, so students can apply to attend schools outside of their assigned zone. This neighborhood has a number of schools nearby, including:
Jackie Robinson Elementary School, a highly rated public K-3
University of Chicago Charter School Donoghue Campus, a public charter that's one of a few UChicago campuses
Wendell Phillips Academy High School, one of the oldest African American high schools in the city
For a private option, Christ the King School is a Catholic K-8 that’s been in the neighborhood for almost 90 years.
Wendell Phillips Academy High School is a historic landmark in South Side.
Wendell Phillips High School serves the Oakland residents.
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Norms Bistro is a popular destination for Oakland residents, with live music on the weekends.
Stop in Norman's Bistro and shop nearby
Since Oakland is mostly residential and parks, you’ll have to venture outside the neighborhood for shopping and dining. Norman’s Bistro is Oakland’s only restaurant, but it is a community favorite. “People spend a lot of time there, especially watching Sunday football,” Flanagan says. Its menu features plenty of Southern comfort food, like fried catfish and gumbo. Lake Meadows Shopping Center is right next door and includes a Jewel-Osco and fast-food chains that are still within walking distance of homes. Neighboring Bronzeville has more local restaurants and chains where you can stop in for a bite to eat.
What's walkable and how to commute from Oakland
This neighborhood is somewhat walkable. Neighborhood parks and nearby shopping centers mean you can get plenty of places on foot. “We also have these new pedestrian bridges that were completed in 2018. They’re an architectural marvel,” Flanagan says. “You walk over the bridge, and it’s like you’re instantly hanging out at Oakwood Beach.” Buses stop along Cottage Grove Avenue and Muddy Waters Drive, and there are bike lines on Cottage Grove, Oakwood Boulevard and Pershing Road.
Still, you’ll likely need a car when getting around South Side or commuting to The Loop, about a 15-minute trip on Lake Shore Drive. While Metra tracks run through the neighborhood, it doesn’t stop in Oakland.
Lake Shore Drive quickly connects Oakland residents to downtown Chicago.
Bus routes frequently run on main thoroughfares, making commuting in Oakland a breeze.
Commuting in Oakland is easy with covered bus terminals and active routes.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Are you familiar with the Oakland neighborhood?
to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Oakland
US
Homicide
4
4
Sexual Assault
9
4
Assault with Weapon
7
4
Robbery
7
4
Burglary
4
4
Motor Vehicle Theft
5
4
Larceny
5
4
Crime Score
8
4
Source: WhatIsMyCrimeRisk.com
Oakland Demographics and Home Trends
On average, homes in Oakland, Chicago sell after 41 days on the market compared to the national average of 53 days. The median sale price for homes in Oakland, Chicago over the last 12 months is $350,000, up 4% from the median home sale price over the previous 12 months.
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