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Oakland Townhomes for Sale

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  • 3993 S Drexel Blvd, Chicago, IL 60653
    3993 S Drexel Blvd, Chicago, IL 60653
    3993 S Drexel Blvd, Chicago, IL 60653
    /7

    $415,000

    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    3993 S Drexel Blvd, Chicago, IL 60653

    Classic Elegance Meets Contemporary Living These beautifully designed townhomes echo the charm of neighboring landmark-status residences, offering timeless curb appeal with modern interiors. Inside, you'll find: * Three spacious bedrooms and three-and-a-half baths, thoughtfully laid out for comfort and convenience * A dramatic double-height living room filled with natural light, thanks to

    Barbara Bracy Baird & Warner

    3993 S Drexel Blvd, Chicago, IL 60653
  • 4114 Maryland Ave, Chicago, IL 60653
    4114 Maryland Ave, Chicago, IL 60653
    4114 Maryland Ave, Chicago, IL 60653
    /26

    $384,900

    • 3 Beds
    • 2 Baths
    • 2,200 Sq Ft

    4114 Maryland Ave, Chicago, IL 60653

    4114 S Maryland Avenue | A home that adapts to your rhythm This radiant 3-level corner townhome offers over 2,200 sq ft of thoughtfully designed living space in the heart of North Kenwood/Oakland. With 3 bedrooms, 2 baths, and a spacious lower-level family room that easily transforms into a 4th bedroom, guest suite, or dedicated office, this home flexes to meet your needs-whether you're

    Carolyn Durocher Coldwell Banker Realty

    4114 Maryland Ave, Chicago, IL 60653
Illinois Cook County Chicago Oakland

Townhomes for Sale in Oakland, Chicago

Why Live in Oakland
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 ...
Learn more about living in Oakland

Home Trends in Oakland, IL

On average, homes in Oakland, Chicago sell after 79 days on the market compared to the national average of 52 days. The median sale price for homes in Oakland, Chicago over the last 12 months is $335,000, down 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$335,000
Median Single Family Sale Price
$659,000
Median Townhouse Sale Price
$341,000
Median 2 Bedroom Sale Price
$219,200
Median 1 Bedroom Sale Price
$196,000
Average Price Per Sq Ft
$199
Number of Homes for Sale
9
Last 12 months Home Sales
23
Months of Supply
4.70
Median List Price
$367,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-11%
How to Buy a Home How to Finance a Home How to Sell a Home

In Oakland, there are currently 2 townhouses for sale, offering a variety of options for potential buyers. With townhouses ranging from $384,900 to $415,000, there's something for every budget. As of September, 2025 the median home price in Oakland, Chicago is $367,000, while the average sale price is $393,373, providing insight into local market trends. On average, townhouses spend 79 days on the market before being sold. Whether you're interested in modern townhouses, small townhomes, or traditional rowhouses, there are options available to suit your needs. Browse properties and townhomes for sale in Oakland, Chicago, and discover the ideal residence to fit your needs.

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