Oakland, Chicago, IL, Real Estate

Oakland is located on the South Side of Chicago, Illinois. Oakland is one of 77 officially designated Chicago community areas.

Oakland currently has 2 single family homes for sale with an average list price of $634,500 and 11 condos for sale with an average list price of $366,472.64. The average annual property tax for Oakland is $5,403.64.

Current Homes for Sale

Schools

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What's Hot & What Not

Absorption Report Using the absorption rate, we can determine how long it's taking for homes to sell and which price points are selling the fastest in Oakland, i.e. what's hot and what's not.

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Recent Sales

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Buildings/Subdivisions

Buildings/Subdivisions Median Price
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3968 S. Ellis

3968 S. Ellis is a condo building in the Oakland neighborhood of Chicago, Illinois, built between 2004 and 2007. It currently has 1 condo for sale with a list price of $425,000. The homes have an average size of 2,200 ft2. The HOA fees range from $321 to $418 per month. The average annual property tax for 3968 S. Ellis is $7,159.00. It is located in Cook County. 3968 S. Ellis Avenue is an 8 unit condo building. 3968 S. Ellis Avenue is located in the Oakland neighborhood of Chicago. ... Read more
Median Price: $403,000
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3971 S. Ellis

3971 S. Ellis is a condo building in the Oakland neighborhood of Chicago, Illinois, built between 2004 and 2005. It currently has no homes for sale. The homes range in size from 1,750 ft2 to 2,200 ft2. The average annual property tax for 3971 S. Ellis is $5,217.74. It is located in Cook County. 3971 S. Ellis Avenue is an 8 unit condo building built in 2004. 3971 S. Ellis Avenue is located in the ... Read more
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4043 S. Drexel

4043 S. Drexel is a condo building in the Oakland neighborhood of Chicago, Illinois. It currently has no homes for sale. It is located in Cook County. 4043 S. Drexel Blvd. is a 12 unit condo building built in 2003. 4043 S. Drexel is located in the Oakland neighborhood of Chicago. ... Read more
Median Price: $372,239
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4102 S. Cottage Grove

4102 S. Cottage Grove is a condo building in the Grand Boulevard neighborhood of Chicago, Illinois. It currently has no homes for sale. The homes range in size from 2,400 ft2 to 2,700 ft2. The HOA fees range from $309 to $309 per month. The average annual property tax for 4102 S. Cottage Grove is $4,330.17. It is located in Cook County. 4102 S. Cottage Grove Avenue is a 12 unit vintage condo-duplex building. 4102 S. Cottage Grove Avenue is located in the Grand Boulevard neighborhood of Chicago. ... Read more
Median Price: $325,000
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4105 S. Drexel

4105 S. Drexel is a condo building in the Oakland neighborhood of Chicago, Illinois, built in 2004. It currently has 1 condo for sale with a list price of $379,900. The homes range in size from 1,050 ft2 to 1,800 ft2. The HOA fees range from $485 to $589 per month. The average annual property tax for 4105 S. Drexel is $4,673.37. It is located in Cook County. 4105 S. Drexel Blvd. is a 14 unit condo building built in 2003. 4105 S. Drexel Blvd is located in the Oakland neighborhood of Chicago. ... Read more
Median Price: $340,000
Show all 11 Buildings/Subdivisions

Buildings/Subdivisions

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Market Trends

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Real Estate News

Homes Just Sold in Oakland: April 28th to May 4th

Homes Just Sold in Oakland: April 28th to May 4th - May 5, 2026

Oakland had only 1 sale during the week of Tuesday, April 28 to Monday, May 4, including and it was a condo for sale with a list price of $435,000. $435,000 3945 ... continue reading
New Homes For Sale This Week in Oakland: April 24th to April 30th

New Homes For Sale This Week in Oakland: April 24th to April 30th - May 1, 2026

Oakland had only 1 new home for sale during the week of Friday, April 24 to Thursday, April 30, including and it was a condo for sale with a list ... continue reading
Homes Just Sold in Oakland: April 21st to April 27th

Homes Just Sold in Oakland: April 21st to April 27th - April 28, 2026

Oakland had only 1 sale during the week of Tuesday, April 21 to Monday, April 27, including and it was a condo for sale with a list price of $439,000. $439,000 4029 ... continue reading
New Homes with Master Bedrooms on the 1st Floor in Oakland: April 18th to April 24th

New Homes with Master Bedrooms on the 1st Floor in Oakland: April 18th to April 24th - April 25, 2026

Oakland had 4 new homes for sale with a master bedroom on the first floor during the month of Saturday, April 18 to Friday, April 24, including 4 condos ... continue reading
New Homes For Sale This Week in Oakland: April 17th to April 23rd

New Homes For Sale This Week in Oakland: April 17th to April 23rd - April 24, 2026

Oakland had 5 new homes for sale during the week of Friday, April 17 to Thursday, April 23, including including 1 single family home for sale with a list price ... continue reading
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