Oakland · Cook County · IL
Homes for sale in
Oakland.
- Active listings
- 5
- Median list
- $720K
- Avg time on market
- 21 days
- Sold · last year
- 29
Active listings
5 homes on the market
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About the community
Living in Oakland.
Oakland is Chicago Community Area 36, set on the South Side along Lake Michigan and bounded by 35th and 43rd Streets, Cottage Grove Avenue, and Lake Shore Drive. At just 0.60 square miles it is the smallest community area by land area in Chicago, and the 2020 Census counted 6,799 residents, for a density of roughly 11,400 people per square mile. The community is predominantly Black, recorded at 86.7 percent in 2020, and sits within the broader Bronzeville area on the South Side. Its housing stock is heavily multi-family, with about 73.6 percent of units in buildings of five or more units and a median year built of 1994, reflecting the redevelopment that followed the demolition of older public housing. The lakefront is the neighborhood's signature amenity, anchored by Burnham Park and the Oakwood, or 41st Street, Beach. Daily life is notably car-light, with roughly 42 percent of households owning no vehicle and about a quarter of workers commuting by transit. Buyers are drawn by the rare combination of a lake-adjacent location, proximity to the Loop, and a mix of historic boulevard architecture and newer single-family and townhome construction.
At a glance
Population
6,799 residents as of the 2020 Census, up about 14.9 percent from 2010, in one of Chicago's smaller community areas.
Location
A South Side community area along Lake Michigan, bordered by 35th and 43rd Streets, Cottage Grove Avenue, and Lake Shore Drive, in ZIP 60653.
Size and density
Chicago's smallest community area by land area at 0.60 square miles, with a density of about 11,400 people per square mile.
Walk Score
The heart of Oakland near Oakwood Boulevard and Cottage Grove Avenue rates a Walk Score of 66, a Transit Score of 59, and a Bike Score of 76.
Transit and commute
About a quarter of workers commute by transit and roughly 42 percent of households have no vehicle, with a mean commute of about 31 minutes.
Median home price
Redfin lists the Oakland neighborhood median sale price around 292,970 dollars, a figure that can swing sharply given the small market.
Parks and lakefront
Burnham Park, including the roughly seven-acre Oakwood, or 41st Street, Beach, lines the community's lakefront.
Diversity
A predominantly Black community, recorded at about 86.7 percent in 2020, within the historic Bronzeville area.
What it’s actually like to live here
Daily life in Oakland is shaped by its small footprint and its lakefront edge. The center of the neighborhood rates as somewhat walkable with a Walk Score of 66, a Transit Score of 59, and a strong Bike Score of 76, and many residents live car-light, with about 42 percent of households owning no vehicle and roughly a quarter of commuters taking transit. The CTA Green Line runs just west of the community through Bronzeville, with stops such as 43rd serving the area. The standout amenity is the lakefront, where Burnham Park and the roughly seven-acre Oakwood, or 41st Street, Beach sit right at the community's eastern edge, and the Lakefront Trail connects residents to the rest of Chicago's shoreline.
The housing character blends eras, from historic mansions and greystones along Drexel Boulevard to a large share of mid-size apartment buildings and newer single-family homes and townhomes built since the 1990s redevelopment, giving the area a median year built of 1994. Roughly a quarter of occupied units are owner-occupied, so the market includes both rental and for-sale options. The current Redfin neighborhood median sale price is about 292,970 dollars, and because the area is small the reported year-over-year swings should be read as a snapshot rather than a long-term trend. For dining and errands, residents also draw on the adjacent Bronzeville and Kenwood corridors along Cottage Grove Avenue and 47th Street.
Around town
What there is to do in Oakland.
A handful of the places people who live here actually use. Not a directory.
- Recreation
Oakwood (41st Street) Beach
This roughly seven-acre Lake Michigan beach at 41st Street forms Oakland's lakefront front yard. Its LEED-certified beach house includes restrooms and a rainwater-harvesting system, and the site offers distance swimming parallel to the shoreline. It connects directly to the Lakefront Trail and Burnham Park.
- Parks
Burnham Park
Stretching along the South Side lakefront, Burnham Park was named for architect and planner Daniel H. Burnham, whose 1909 Plan of Chicago envisioned this lakefront greenway. The park includes several beaches, among them Oakwood at 41st Street, plus meadows, trails, and playfields. It gives Oakland residents miles of waterfront recreation steps from home.
- Family
Mandrake (Henry Brown) Park
This roughly 10-acre neighborhood park at 900 East Pershing Road offers tennis and basketball courts, two baseball diamonds, a quarter-mile running and walking track, and picnic areas. It is named for local activist Henry McNeil Brown, known for grassroots work removing alcohol and tobacco billboards. The park hosts athletics programs including track and flag football.
- Culture
Abraham Lincoln Center
Built in 1905 at 700 East Oakwood Boulevard, this early Frank Lloyd Wright-associated commission was developed with Dwight Perkins for a Unitarian congregation. After a 1978 renovation it became home to Northeastern Illinois University's Carruthers Center for Inner City Studies. It remains one of the neighborhood's most significant historic landmarks.
- Culture
Drexel Boulevard Historic Homes
Drexel Boulevard preserves some of Chicago's grand old homes from Oakland's late-19th-century heyday as an elite enclave. The boulevard's mansions and greystones reflect the architecture of the 1872 to 1905 building era. A portion of Oakland's historic fabric was designated a Chicago Landmark in 1992.
- Recreation
CTA Green Line at 43rd Street
The CTA Green Line runs just west of Oakland through Bronzeville, offering a direct rapid-transit link to the Loop and the rest of the L system. Stations including 43rd put downtown jobs and amenities within an easy ride. The line is a key reason many Oakland residents live car-light.
By the numbers
Oakland taxes + market stats.
Property tax rates vary by exact township and assessor district. Confirm per address before pricing a purchase.
Median sold price
$354,000
MRED · last 12 mo (29 sales)
How Oakland got here
A bit of history.
Oakland grew out of a lakeside settlement called Cleaverville, founded after industrialist Charles Cleaver bought 22 acres near 38th Street and Lake Michigan in 1851. Developers subdivided the land and renamed it Oakland in 1871, and the area was largely built out between 1872 and 1905. The 1881 arrival of the Illinois Central Railroad terminal at 39th Street and Cottage Grove, known as the Five Crossings, spurred growth, and for a time Oakland was home to many of the city's elite, leaving grand homes still visible along Drexel Boulevard. During the Great Migration around 1916 to 1920 many African Americans settled in Oakland, and by 1950 the area was roughly 77 percent Black as restrictive covenants gave way.
From 1939 to 1970 the Chicago Housing Authority built a series of public housing projects here, including the Ida B. Wells Homes, the Clarence Darrow Homes, the Lake Michigan High-Rises, and Madden Park Homes, which reshaped the community. The neighborhood declined through the late 20th century, and in March 1992 the Chicago City Council designated a portion of Oakland a Chicago Landmark. Beginning in the 1990s the Kenwood-Oakland Community Organization rehabilitated buildings and pressed the city to reinvest, and a Parade of Homes promoted new single-family houses, townhomes, and rehabbed buildings. The high-rises were demolished over an eleven-year span, with the last four Lake Michigan High-Rises imploded in December 1998 and replaced by new mixed-rise housing such as Sullivan Station.
The questions buyers actually ask
Oakland FAQ
The questions I get most from buyers shopping Oakland. If yours isn't here, text 224-385-8779, same-day reply.
- What kinds of homes are for sale in Oakland, and what do they cost?
- Oakland offers a mix of historic boulevard homes and greystones, mid-size apartment buildings, and newer single-family houses and townhomes built since the 1990s redevelopment. The housing stock skews multi-family, with about 73.6 percent of units in buildings of five or more units and a median year built of 1994. Redfin currently lists the neighborhood median sale price around 292,970 dollars. Because the community is small, sale prices and year-over-year figures can move sharply from quarter to quarter.
- How is the commute to downtown Chicago?
- Downtown is close and well connected. The CTA Green Line runs just west of the neighborhood through Bronzeville, providing a direct ride to the Loop. Regional planning data shows the mean commute time is about 31 minutes, and the Loop is the single most common work destination for Oakland residents. Lake Shore Drive also borders the community for drivers heading north into the city center.
- Is Oakland walkable, or do I need a car?
- Many residents live without a car. About 42 percent of households have no vehicle available, and roughly a quarter of workers commute by transit. The center of the neighborhood rates a Walk Score of 66, a Transit Score of 59, and a strong Bike Score of 76. For larger shopping trips, residents also use the nearby Cottage Grove and 47th Street corridors in adjacent Bronzeville and Kenwood.
- What is the neighborhood's character and diversity like?
- Oakland is a predominantly Black community, recorded at 86.7 percent in the 2020 Census, and is part of the historic Bronzeville area on the South Side. It is one of Chicago's smaller communities at about 6,799 residents, which gives it a close-knit feel. The population grew about 14.9 percent between 2010 and 2020, reflecting continued reinvestment. It blends longtime residents with newcomers drawn to the lakefront location.
- What parks and recreation are nearby?
- Oakland's biggest draw is its lakefront. Burnham Park lines the shore with beaches, trails, and playfields, including the roughly seven-acre Oakwood, or 41st Street, Beach with its LEED-certified beach house. Inland, Mandrake, or Henry Brown, Park offers tennis and basketball courts, ballfields, and a quarter-mile track. The Lakefront Trail connects residents to the rest of Chicago's shoreline for biking and walking.
- Does Oakland have notable history or landmarks?
- Yes. The neighborhood began as Charles Cleaver's 1851 lakeside settlement called Cleaverville and was renamed Oakland in 1871. The Abraham Lincoln Center at 700 East Oakwood Boulevard, an early Frank Lloyd Wright-associated 1905 building, now houses Northeastern Illinois University's Carruthers Center for Inner City Studies. A portion of Oakland was designated a Chicago Landmark in 1992, and grand historic homes still line Drexel Boulevard.
- Who is the real estate agent for Oakland?
- Joe Keegan is the local licensed Illinois real estate broker who covers Oakland in Oakland, IL through Subdiview, a neighborhood-first home search for the Chicago suburbs and collar counties. Joe prices and negotiates from the live MRED sold comps for Oakland specifically, not national averages, and can help you buy or sell here. Reach Joe at 224-385-8779 or joe@joekeeganhomes.com.
Nearby
Neighborhoods near Oakland.
If you’re cross-shopping the area, these are the neighborhoods right next to Oakland.
Your local agent
Joe knows Oakland
Most agents will list anything. I focus on the places I actually know, and the things that move value here don't show up in the MLS write-up: which streets and buildings hold demand, what the HOA or assessments really cover, how the comps read once you account for condition and location, and where buyers consistently want to be.
When you're ready to tour or list, you want someone who has read the last 50 closed comps in this specific market, not a national average, and can tell you what they actually mean for your price. That's how I work. Text or call any time, and I'll give you a real take, not a brochure.
- Licensed Illinois broker
- Comp-driven pricing
- Oakland specialist
- Honest local market take
- Brokerocity
Thinking of selling?
What's your home actually worth?
Not a Zestimate. A real CMA from someone who's sold this neighborhood, knows the floor plan premiums, and can tell you which upgrades the buyer pool here actually pays for.
- Pricing range with comp-by-comp logic
- Pre-list improvements that pay back, and the ones that don't
- No obligation, no spam, no auto-dialer