$438,115Average Value$198Average Price per Sq Ft5Homes For Sale
A century of progress on Lake Michigan
Oakland’s identity is firmly rooted in its evolution over the last century. Located next door to Bronzeville, a hub for African-American culture and business in the early 1900s, the community was long a casualty of historic redlining and housing discrimination. By the hands of local activists, Oakland today is compact with affordably-priced single-family homes, townhouses and condos—and new investors are still breaking ground. “As a homeowner, it’s great to see construction in our community because it brings equity to our homes,” says Shaena Flanagan, an Oakland resident and Luxury Property Specialist with Coldwell Banker Realty. “There were so many empty lots for so long; a lot of housing projects were finally torn down, and they’re never going back up.” The bustling community is home to locally-owned restaurants, shops and parks overlooking Lake Michigan. Residents even share monumental landmarks with neighboring Bronzeville, including Wendell Phillips Academy High School, the oldest predominately African-American high school in the city.
Oakland offers wonderful views of downtown Chicago.
Oakland is a few miles south of Chicagos downtown Loop area.
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The Oakland Renaissance
At the height of the midcentury, the Chicago Housing Authority constructed several public housing projects in and around Oakland. Over the decades, a select few were converted into high-rise apartments while the rest were demolished in favor of reinvesting in single-family homes and townhouses. The effort, led by activist Shirley Newsome, has led to years' worth of redevelopment, with new properties coming online as recently as 2022. "In the 1990s, Oakland was one of the poorest Chicago communities," Flanagan says. "But we've seen so much evolution thanks to decades of Black homeowners investing in the area. These middle-class families have built equity here, and now there's new construction every day." While contemporary builds are common, Queen Anne homes constructed in the late 19th century still line Berkely and Ellis Avenues. These properties, which come with detached garages out back, are priced between $375,000 and $745,000, with the occasional 4,000-square-foot home exceeding $1 million. Three-story townhouses with brick façades sit closer to Drexel Boulevard, complete with wrought-iron gates and attached garages priced between $320,000 and $415,000. Condos are scattered throughout Oakland, occupying stone and brick buildings dating back to the early 20th century. Units typically range in price from $150,000 to $550,000.
Oakland homes from the 1800's sometimes feature historic mailboxes.
Oakland features unique homes from the 1800's.
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Soul food & community at Norman’s Bistro
On the corner of Muddy Waters Drive and Ellis Avenue sits Norman’s Bistro, a locally owned restaurant geared towards bringing the community together. “They have fried catfish, collard greens, mac and cheese; all of that southern flavor,” Flanagan says. “And people spend a lot of time there, especially watching Sunday football. One Stop [Food & Liquors] is down the street, which opened in the 1920s before many of our homes were even built.” The wholesale market has served loyal patrons for decades, a go-to for families like Flanagan’s who live within walking distance. A mile north, off of 33rd Place, Lake Meadows Shopping Center houses a Jewel-Osco, Walgreens and classic Midwest fast food stops like White Castle and Culver’s. Nearby, the Bronzeville Winery pays tribute to the community’s rich history through live blues and jazz performances, as well as a rotating wine list of minority- and African-American-owned labels.
Norms Bistro is a popular destination for Oakland residents, with live music on the weekends.
Tabbys Closet on East 43rd Street brings contemporary women's clothing and jewelry to Oakland.
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Fundraisers and social awareness through a local grassroots organization
Each August, the Kenwood Oakland Community Organization — a grassroots, membership-based group of residents with strong ties to the Bronzeville and Oakland areas — hosts KOCO Fest at Mandrake Park. Locals flock to the festival yearly to catch old-school blues performances, peruse food trucks and partake in family-friendly entertainment, including bounce houses and backpack giveaways for students. KOCO also hosts fundraisers and social awareness events, like We Walk for Her, a community march raising awareness for missing Black girls and women in Chicago. Over on Lake Park Avenue, the Oakland Museum and Garden may appear at first like someone’s eclectic backyard. But the spot is actually dedicated to Milton Mizenburg Jr., a beloved late Oakland resident who carved the wooden sculptures scattered across the otherwise vacant corner lot. The garden is one of many hidden nooks cherished by locals. Other landmarks and attractions include The Light of Truth Ida B. Wells National Monument at Ellis Park and Faie African Art Gallery, next door to Norman’s Bistro.
Oakland is homes to the Oakland Museum and Garden.
Opened in 2016, the Arts and Rec Center at Ellis Park offers 32,000 square feet of amenities.
Phillips Academy High School earns a C minus from Niche.
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Summers well spent at Oakwood Beach
Ellis Park borders Oakland to the north. Established in the early 20th century, Ellis is considered one of Chicago’s oldest parks. Paved walking paths intertwine between tennis courts and ball fields, hosting local athletic leagues for practices. The park’s indoor pool complies with the Americans with Disabilities Act and is located within the Ellis Arts and Recreation Center. Just south, Mandrake Park is known for its athletic track. “I like to get up early and walk there,” Flanagan says. “It’s beautiful, especially since the groundskeepers come by regularly to maintain the park. It’s also where everyone goes for kids club sports since they host their games over there.” The Lake Michigan waterfront is a hot spot for walkers and cyclists taking advantage of Burnham Park’s paved paths and concrete shoreline that gives way to sandy beaches complete with seasonal snack bars and a photo-ready mermaid sculpture.“We also have these new pedestrian bridges that were completed in 2018; they’re an architectural marvel,” she continues, referring to Oakland’s 35th and 41st Street bridges. “You walk over the bridge, and it’s like you’re instantly hanging out at Oakwood Beach. All of us families spent a lot of time there this summer.”
As the sunsets a biker races home along Oaklands Lake Front Trail.
Summer is well spent on the sandy shores of Oakwood Beach.
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The home of Gwendolyn Brooks & the Savoy Big Five
Oakland students attend Chicago Public Schools. Many kids begin at James Farmer Jr. Elementary School, a K-8 institution with a C-minus on Niche. Formerly known as Melville W. Fuller Elementary, the school changed its name in 2024 to reflect the South Side’s civil rights history. Students engage in social-emotional learning and restorative practices through partnerships with CPS Tutor Corp and City Year, a nonprofit dedicated to mentorship for academic, interpersonal and workforce skills. Wendell Phillips Academy High School, a Bronzeville landmark that first opened in 1904, earns the same grade. Known as the oldest predominately African-American high school in Chicago, Wendell Phillips Academy was the alma mater of many prominent figures, including Gwendolyn Brooks, Nat “King” Cole and even the Savoy Big Five—the original members of the Harlem Globetrotters. Private school options include Holy Angels Catholic School, which opened in 1887. The K-8 institution provides ample scholarships and early education programming at a reduced rate for accessibility.
Phillips Academy High School
Wendell Phillips High School serves the Oakland residents.
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Riding the Metra from 47th to The Loop
Oakland drivers are a 4-mile commute to Downtown Chicago on Interstate 41, accessible via East Oakwood Boulevard. Though many single-family homes, townhomes and condos offer private garages and parking pads for personal vehicles, residents still heavily rely on public transportation to reach The Loop. Chicago Transit Authority bus stops line Oakland’s residential streets, primarily along Cottage Grove Avenue and 43rd Street. Those seeking train stations will find that the nearest CTA platform is a mile west—the Green Line’s Indiana Avenue stop. Most opt to take the Metra from 47th Street’s Kenwood station. Bike lanes on Cottage Grove Avenue head 2 miles south to Washington Park and Bynum Island, while those on Oakwood Boulevard connect Mandrake Park to Oakwood Beach. From there, cyclists can take the scenic Lakefront Trail all the way north to The Loop. Mercy Care Center provides urgent care in Oakland. Emergency services are offered at Insight Hospital & Medical Center in the Motor Row District and UChicago Medicine in Hyde Park—both 2 miles away. Chicago Midway International Airport is 9 miles west.
Residents of Kenwood can hop onto the Metra rail line to commute to downtown Chicago.
Commuting in Oakland is easy with covered bus terminals and active routes.
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Houses of worship giving back in Oakland
Houses of worship are prominent throughout the Oakland community, often within walking distance of most homes. The community scores a 6 out of 10 on the CAP Crime Index, but scores for certain violent crimes are even higher. Through service, groups associated with the faith communities combat issues related to crime. From Grant Memorial AME Church to Holy Angels Covenant, Evening Star MB Church and The CityLight Church, many are community-oriented. “They have back-to-school events where they give out school supplies and food to the parents of students,” Flanagan says. “That’s one thing about the churches here: They give back.”
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
There is some activity when it comes to sports, and their is always news around whether it is good or bad.
2.0Niche User
8/15/2016Niche Review
People in the area are not in the best of direction for their selves and could use help for better help.
2.0Niche User
6/18/2014Niche Review
We only have football games by the track field and at times we have african american fairs.
2.0Niche User
10/25/2015Niche Review
Living in Chicago is beautiful but as a youth everyday I feel I could possibly lose my life due to all the gang violence that takes place here. Its scary to think that as a child living here you may not make it to see the age 18, or even see college. Not even just that we are labeled one of the murder capitols of America. People don't even call Chicago by its name, most people call it "Chi-raq" because of all the deaths. For me that is very scary to live in, and everyday I can't wait to get out of here. I love my hometown of course but I'd love to see it improve. I'd love to see government officials stand up and make our city great again. Change is all Chicago needs.
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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 48 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 $367,500, up 12% from the median home sale price over the previous 12 months.
Experience the perfect blend of space and style in this stunning 2-bedroom, 2-bath loft-style condo. The open floor plan is ideal for both everyday living and entertaining, featuring a modern kitchen with granite countertops, stainless steel appliances, and plenty of cabinet space. Both bedrooms are generously sized and offer ample closet space. Enjoy the convenience of in-unit laundry and unwind
Spacious 3 Bed / 2 Bath Condo in Historic Bronzeville-Oakland | 1,800 Sq. Ft. | Parking Included. Experience classic Chicago architecture and modern comfort in this expansive 1,800 sq. ft. condo ideally located in the historic Oakland neighborhood, bordering vibrant Bronzeville-a community celebrated for its cultural legacy and ongoing revitalization. This bright, well-designed 3-bedroom, 2-bath
John Hockberger@properties Christie's International Real Estate
Beautiful, spacious, and light-filled 2-bedroom, 2.5-bath duplex located in the highly sought-after Oakland/Bronzeville neighborhood! This rarely available home offers a modern open layout, granite countertops, stainless steel appliances, and a cozy fireplace. Both bedrooms are generously sized, providing plenty of comfort and space. Perfectly situated near shops, restaurants, and Lake Shore
Move in ready & just in time for the holidays! This beautiful 3BD/2BA condo located on the historic Drexel Boulevard in the Oakland Community, features a spacious open living/dining area with a cozy fireplace, well-appointed kitchen with ample cabinet space, and in-unit laundry. The primary ensuite includes his-and-her closets and a spa-like bath with a jacuzzi tub, separate shower, and heated
INCOME RESTRICTION: Individual - $50,400, Two People - $57,600, Three People - $64,800New AppliancesLuxury Vinyl Plank Flooring in Kitchen, Foyer, and BathOutstanding Lake, Skyline, and City ViewsWalking Distance to Grocery, Shopping, and Fitness Nearby (Lake Meadows Shopping Center)Ground Floor Laundry Room with new Laundry Equipment (2021)Steps
Luxury living at its finest, new construction 2023 This modern property boast an elegant living experience with stylish, spacious floor plans. Apartment features open floor plan with 9 ft. ceilings, private terraces, and abundant natural light. Additional finishes include hardwood floors, high efficiency furnace and hot water tank, sprinkler system, A/C, in-unit washer and dryer, and stylish
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