Chicago, Illinois Homes for Sale

About Oakland

Bordering the coast of Lake Michigan, Oakland is a quiet neighborhood on Chicago's south side. With scenic views of the glittering lake and Chicago's towering skyline, this promising neighborhood is sure to continue growing in the coming years.

Quick Facts

Current Prices: $165,000 to $999,900

Closed Prices: $149,900 to $780,000

Median Sale Price: $337,000

Average $ per sq ft: $226

Association Fee Ranges: $150/quarter, $0 to $179, $111 to $387/mo

Type: Attached Home (Condo, Townhouse, Loft, etc.), Single-Family Home

Age: 1873 to 2021

Sq. Ft.: 850 to 6049 Sq. Ft.

Bedrooms: 1 to 5 Bedrooms

Bathrooms: 1 to 5 Bathrooms

Around Oakland

Oakland’s residences are all found to the west of Lake Shore Drive while the land to the east of this major expressway is dedicated to public parks. With several bridges connecting pedestrians to the lake path, homeowners anywhere in Oakland can easily reach the city's coastal green spaces. Many homes in this lakeside neighborhood are surprisingly affordable, though there are more luxurious options as well as vintage rehabs that merit a higher price tag.

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.

The population here is spirited and hardworking, dedicating much of their time and effort toward the continued rejuvenation of the neighborhood. They are quick to meet and organize, working with city officials and each other to ensure the area keeps trending in the right direction. To that end, Oakland residents are very welcome to new neighbors, especially those that show a passion for being in the area and helping it succeed.

Art enthusiasts can check out one of the local galleries for a variety of displays from Oakland artists. Just as the community is quick to support each other in creative endeavors, they will also celebrate successes together with gatherings at one of the local dance venues. While there aren’t many bars in the area, there are a few classy joints where you can enjoy a glass of fine wine on a special evening out.

Join your neighbors at a restaurant where you can take your time with lunch and coffee. These establishments often host live music on Sundays, so even if you're not in the mood for dessert, stick around for some classic Chicago jazz. Afterwards, head to Mandrake Park to burn off some calories with a pickup game on the basketball courts or take a walk to Oakwood Beach and watch the waves roll in.

Locals Love

  • Community gatherings
  • Proximity to Lake Michigan
  • Local art scene

Locals Don't Love

  • Traffic on Lake Shore Drive
  • No nearby train stations

Neighborhood Reviews

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buyers and sellers in this neighborhood.