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Do Oprah’s Real Estate Investments Make Money?

Some of her properties in Chicago and in Indiana sold for a profit. But those Lake Shore Drive places have gotten walloped.

Given that she hasn’t worked in Chicago since 2011, it’s hard to fault Oprah Winfrey for slimming down her real-estate portfolio here. So nobody was terribly surprised when the media mogul announced in a September memo to employees that she was looking to unload her mammoth Water Tower condo, according to the website Chicago Real Estate Daily. As of presstime, Winfrey had yet to list the property, but based on industry estimates, she stands to make a significant profit. If so, that would redress the balance of winning and losing real-estate investments she’s made in the area. Check out the details.

Condo at Water Tower Place
Photo: Ratko Radojcic

For Sale

Condo at Water Tower Place

Purchase price for four condos:
Unit 5703 (1985): estimated $350,000
Unit 5603 (1992): $531,250
Unit 5602 (1993): $1.5 million
Unit 5601 (1994): $1 million
Estimated sale price: $10 to $12 million

In about 1995, Winfrey combined four condos into one 11,000-square-foot duplex on the 56th and 57th floors. The residence will fetch between $10 and $12 million, according to an agent with expertise in luxury properties who asked not to be named. (A spokesperson for Winfrey declined to comment.) Even at the low end, that would represent a profit of nearly $7 million over what the star paid. (It excludes her renovation costs, however.) Don’t expect a price bump just because Oprah owned the place, says the agent: “The draw of Oprah’s name may be of interest to some, but that has not been proven to be true with athletes and movie stars.”

 

Condo at 219 E. Lake Shore Dr.
Photo: Ratko Radojcic

Sold

$460,000 loss
Condo at 219 E. Lake Shore Dr.

Purchase price (1988): $2.54 million
Sale price (1993, 1994): $2.08 million total

Winfrey bought an entire floor in the tony building and sold the units separately. “The market on Lake Shore Drive in 1993 had completely fallen,” explains a veteran Gold Coast broker. “People were still reeling from the 1987 crash.”

 

Farm in LaPorte County, Indiana
Photo: Courtesy of Koenig & Strey Gold Coast

Sold

$1 million gain*
Farm in LaPorte County, Indiana

Purchase price (1988): estimated $2 million
Sale price (2005): $3.25 million

Winfrey spent millions rehabbing the 164-acre spread, including building a 9,700-square-foot house and an adjacent helicopter pad. She listed the farm at $8.5 million in 2003; it sold for less than half that two years later.

 

Co-Op at 199 E. Lake Shore Dr.
Photo: Ratko Radojcic

Sold

$2.85 million loss
Co-Op at 199 E. Lake Shore Dr.

Purchase price (2006): $5.6 million
Sale price (2012): $2.75 million

Winfrey bought this property at the height of the real-estate boom and sold at a low point. “[Oprah is] willing to take a loss because of her financial situation,” says a veteran Gold Coast agent. Her net worth, according to Forbes: $2.9 billion.
 

NOTE: *ESTIMATED. SOURCES: COOK COUNTY RECORDER OF DEEDS; ORLANDO SENTINEL; CHICAGO TRIBUNE; CRAIN’S CHICAGO BUSINESS

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