Oakland Homes for Sale

Real Estate in Oakland, Chicago Illinois

Oakland, located on the South Side of Chicago, Illinois, USA, is one of 77 officially designated Chicago community areas with a population of 7,227. Bordered by 35th and 43rd Streets, Cottage Grove Avenue and Lake Shore Drive, The Oakland is in Cook County and it's area was constructed between 1872 and 1905. Once an elegant, Victorian-style suburb on Chicago's south side, Oakland neighborhood is making a strong comeback to reclaim its status as a prominent and flourishing community. With scenic views of the glittering lake and Chicago's towering skyline, this promising neighborhood is sure to continue growing in the coming years. Living in Oakland offers residents an urban feel. With much of the area zoned for residential use, you won’t find many restaurants within Oakland’s borders. However, residents can find several local establishments just outside the neighborhood. Yassa African Restaurant is a popular choice for traditional Senegalese fare, while Norman’s Bistro offers a creative menu of American Creole dishes with a Brazilian twist.

And, for your convenience, feel free to register for a free account to receive email alerts whenever new Oakland Real Estate listings come on the market that match your specific criteria. Or Start here for all Chicago real estate for sale.

Oakland Homes for Sale September 27, 2023
23
Listed
56
Avg. DOM
$207.18
Avg. $ / Sq.Ft.
$430,000
Med. List Price
23 Properties
Page 1 of 2
3
Beds
2F11/2
Baths
1,709
Sq.Ft.
1
Day on Site
11895417
MLS
Fantastic unit in a great building! 3 Bed 2.1 Baths on 2 levels of living space. Ground floor entrance with rear patio outdoor space. Garage parking. Cozy domestic bliss.
4
Beds
1
Baths
2,600
Sq.Ft.
1
Day on Site
11893945
MLS
Stately home on beautiful Lake Park Ave! Need of rehab to bring it back to it's glory. Two stories, back porch, brick 2 car garage, unfinished basement. Vacant lot to the south (4146) also for sale....
2
Beds
1F11/2
Baths
1,150
Sq.Ft.
2
Days on Site
11894746
MLS
Come check out this Oakland 2 bedroom/1.1 bath condo minutes off Lake Michigan Beach! This condo is less then 15 years old, it's has a spacious living room, kitchen with a breakfast bar and newer...
Under Contract
4070 S Lake Park Ave Chicago,  IL 60653
3
Beds
1F11/2
Baths
1,717
Sq.Ft.
8
Days on Site
11889744
MLS
Charming, updated vintage home, close to lakefront/parks, just off LSD. Roof, windows, electric, plumbing 15yrs. Central A/C 2yrs. Water heater 5yrs. Second floor bath has claw foot tub and rain...
4
Beds
3F21/2
Baths
3,500
Sq.Ft.
9
Days on Site
11889159
MLS
Gorgeously updated 4bed/3.2 bath duplex penthouse in the highly desirable Kenwood neighborhood! You will be captivated by the stunning 2-story atrium with floor-to-ceiling windows that stream an...
Open 9/30
4162 S Berkeley Ave Chicago,  IL 60653
3
Beds
3F11/2
Baths
3,000
Sq.Ft.
15
Days on Site
11884995
MLS
Welcome home to this beautiful brick single-family tucked away on a historic and quiet residential street lined with colorful two-story cottages. Open and spacious floor plan with 4 bedrooms and 3.5...
6
Beds
5F11/2
Baths
5,000
Sq.Ft.
18
Days on Site
11841527
MLS
Welcome to the epitome of luxury living in beautiful lakeside Oakland! This magnificent 3-story newer construction home is a true gem and a first-time offering on the market. Boasting over 5,000 sq...
2
Beds
3F11/2
Baths
1,430
Sq.Ft.
20
Days on Site
11878836
MLS
Welcome to the historic Bronzeville! This charming 2-story brick townhome is just a block off of beautiful treelined Drexel Boulevard, a short drive to the area beaches, or a quick bike ride to the...
3
Beds
2F11/2
Baths
1,600
Sq.Ft.
21
Days on Site
11879627
MLS
Spacious Condo unit located in a beautiful Vintage building on highly desired block of Lake Park. Hardwood Floors, Fireplace in Living Room, In-unit washer/Dryer hookup, generous room sizes and large...
4
Beds
3
Baths
2,220
Sq.Ft.
25
Days on Site
11875811
MLS
Immaculate Upgraded Single Family Home with 4 Bedrooms and 3 Full Baths - A Lakefront Gem! Welcome to this meticulously renovated single-family residence that boasts four bedrooms and three full...
7
Beds
4
Baths
27
Days on Site
11874219
MLS
This multi-unit property for sale is located in the Bronzeville neighborhood. It features three units, including a first-floor unit that duplexes down for additional living space, bedroom and...
3
Beds
2
Baths
1,800
Sq.Ft.
27
Days on Site
11874320
MLS
Chicago! Located on historic tree lined Drexel Blvd (4014) this third floor unit features 3 huge bedroom, 2 full baths (one with jacuzzi), open concept living, wood floors throughout, newly installed...

Contact Your Chicago Realtor®

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.