Oakland is Chicago community area 36, a 0.6-square-mile area on the South Side, about 4 miles from the Loop. Oakland is one of the smallest community areas, on the lakefront between Bronzeville and Kenwood. Its parcels include condo units, townhouses and single-family homes, many built in newer developments.
Last reviewed October 4, 2026 · Chicago First Time Home Buyer editorial team
Outline: City of Chicago community area boundary for Oakland. Map data © OpenStreetMap contributors.
At a glance: Oakland
| Fact | Figure |
|---|---|
| Community area number | 36 |
| Part of the city | South Side |
| Size | 0.6 square miles |
| Borders | Douglas, Grand Boulevard, Kenwood |
| Parcels in the Assessor’s 2026 file | 1,756 |
| Houses and townhouses | 335 (19%) |
| Buildings with 2–6 units | 107 (6%) |
| Condo units | 612 (35%) |
| CTA ‘L’ stations inside the area | None |
| City Council wards | 4th Ward |
Homes you will find in Oakland
The Cook County Assessor’s 2026 file lists 1,756 parcels in Oakland. 19% are houses or townhouses, 6% are buildings with two to six units, and 35% are condo units. There are also 103 apartment buildings with seven or more units.
No single home type dominates, so buyers can compare a condo, a house or a two-flat in the same area. Each one fits different loans: condos need building approval for some loans, and two- to four-unit buildings you live in can be financed with FHA. See mortgage options for first-time buyers.
HomeGrown grants can be used for one- and two-unit homes, condos and townhomes, and the grant amount depends on income and on where in the city the home is. IHDAccess Home is available statewide. Compare the two on our side-by-side page.
Getting around
No CTA ‘L’ station sits inside Oakland’s boundary. Most trips start on a CTA bus or by car, and the nearest ‘L’ or Metra station is in a neighboring area. If you will commute downtown, time the trip from the homes you are considering before you make an offer.
Parks and libraries
Chicago Park District facilities sit in 5 parks inside Oakland: Burnham Park, Ellis Park, Holly Park, Mandrake Park, and Williams-Davis Park. There is no Chicago Public Library branch inside Oakland; the nearest is in a neighboring area.
City Council wards
All or nearly all of Oakland is in the 4th Ward. Ward lines do not follow community area lines, so check an exact address with the City’s ward lookup before you contact an alderperson’s office about zoning, permits or city services.
Neighboring community areas
Oakland borders Douglas, Grand Boulevard, and Kenwood. See all 77 community areas.
Common questions
Is Oakland mostly houses or condos?
A mix: 19% of its parcels are houses or townhouses, 6% are 2–6 unit buildings and 35% are condo units. These shares are from the Cook County Assessor’s 2026 parcel file.
Is there an ‘L’ station in Oakland?
No. No CTA ‘L’ station is inside Oakland’s boundary; residents rely on buses, Metra or stations in nearby areas.
What ward is Oakland in?
It is in the 4th Ward. Check a specific address with the City of Chicago’s ward lookup.
Can I use HomeGrown to buy a home in Oakland?
HomeGrown is a City of Chicago program, so homes in Oakland can qualify if the buyer and the property meet its rules. The grant amount depends on household income and the home’s location. See our HomeGrown guide for the current rules.
Sources
- City of Chicago Data Portal, Boundaries – Community Areas
- Cook County Assessor, Parcel Universe (tax year 2026)
- City of Chicago Data Portal, CTA ‘L’ stops
- City of Chicago Data Portal, Chicago Park District park facilities
- City of Chicago Data Portal, Chicago Public Library locations
- City of Chicago Data Portal, Ward boundaries (2023–)
Boundaries, size and neighbors are measured from the City’s official community area boundary. ‘L’ stations, parks and libraries are placed inside the boundary by their coordinates; ward shares are approximate shares of land area. Parcel counts are from the Assessor’s tax year 2026 file, counted October 4, 2026. Houses include townhouses; condo units are counted one parcel per unit.
Cite this page: Chicago First Time Home Buyer, “Oakland, Chicago: A Neighborhood Guide for First-Time Buyers,” reviewed October 4, 2026, chicagofirsttimehomebuyer.com/buying-process/chicago-neighborhoods/oakland/.