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 $844,900, 1 townhouse for sale with a list price of $360,000, and 6 condos for sale with an average list price of $329,050. The average annual property tax for Oakland is $4,886.76.

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 no homes for sale. The homes have an average size of 2,200 ft2. The HOA fees range from $321 to $321 per month. The average annual property tax for 3968 S. Ellis is $6,469.76. 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
Median Price: $385,000
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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 $384,900. 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: $274,100
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4127 S. Drexel

4127 S. Drexel 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 1,300 ft2 to 1,800 ft2. The HOA fees range from $266 to $266 per month. The average annual property tax for 4127 S. Drexel is $2,391.30. It is located in Cook County. 4127 S. Drexel Blvd. is a 12 unit condo building built in 2006. 4127 S. Drexel Blvd. is located in the Oakland neighborhood of Chicago. ... Read more
Median Price: $215,000
Show all 9 Buildings/Subdivisions

Buildings/Subdivisions

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Market Trends

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Real Estate News

New Homes For Sale This Week in Oakland: December 12th to December 18th

New Homes For Sale This Week in Oakland: December 12th to December 18th - December 19, 2025

Oakland had only 1 new home for sale during the week of Friday, December 12 to Thursday, December 18, including and it was a condo for sale with a list ... continue reading
Homes Just Sold in Oakland: December 9th to December 15th

Homes Just Sold in Oakland: December 9th to December 15th - December 16, 2025

Oakland had only 1 sale during the week of Tuesday, December 9 to Monday, December 15, including and it was a townhouse for sale with a list price of $364,900. $364,900 4114 ... continue reading
New Homes For Sale This Week in Oakland: December 5th to December 11th

New Homes For Sale This Week in Oakland: December 5th to December 11th - December 12, 2025

Oakland had 2 new homes for sale during the week of Friday, December 5 to Thursday, December 11, including including 1 single family home for sale with a list price ... continue reading
Homes Just Sold in Oakland: December 2nd to December 8th

Homes Just Sold in Oakland: December 2nd to December 8th - December 9, 2025

Oakland had only 1 sale during the week of Tuesday, December 2 to Monday, December 8, including and it was a condo for sale with a list price of $230,000. $230,000 817 ... continue reading
New Homes with Master Bedrooms on the 1st Floor in Oakland: November 15th to November 21st

New Homes with Master Bedrooms on the 1st Floor in Oakland: November 15th to November 21st - November 22, 2025

Oakland had only 1 new home for sale with a master bedroom on the first floor during the month of Saturday, November 15 to Friday, November 21, and it ... continue reading
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