Oprah Winfrey Sells Home She Never Lived In, Takes Big Loss

Oprah Winfrey Sells Home She Never Lived In, Takes Big Loss

Such is the life of media mogul Oprah Winfrey, who last month closed on the sale of her fancy co-op on Chicago’s Lake Shore Drive, six years after she purchased it. Winfrey reportedly has never called the building “home.” She sold it for $2.75 million, far less than the $5.6 million she bought it for in 2006, demonstrating the new math of the hellish real estate market across the country, where nobody ever seems to sell any property for actual profit anymore.

According to businessinsider.com, the fabulous life of Oprah extends far beyond a co-op in Chicago. For instance, when she’s in Chicago, she stays at a 15,000-square-foot duplex at Water Tower Place on Michigan Avenue. If she’s feeling in a West Coast mood, she might stay at her $52 million estate in Montecito, Calif., that she calls “The Promised Land.” If she wants to go even further then the West Coast, she can fly in her $42 million jet to her lovely farmhouse in Kula, Hawaii. Or she might want to head to the Caribbean, where she has a lavish vacation home on the shores of the laid-back Caribbean jewel. If none of these interest her, she could head to her homes in Telluride, Col., or Douglasvile, Ga., or Lavallete NJ.

The co-op home at 199 E. Lake Shore Drive, features 10-foot high ceilings, a library, solarium, terrace, gourmet custom eat-in kitchen, butler’s pantry, wine room and view of the lake. The unit is one of 13 housed in a Beaux-Arts style building, constructed in 1913 and designed by Benjamin Marshall. The late comedian John Candy lived in the building at one point, and actress Meg Ryan once stayed there while making a movie in Chicago.

Curbed National reported last November that Winfrey had sought to rent out the home for $15,000 a month but got no interest.

Still independent.

We hope this story was worth your time. For over 14 years, Atlanta Black Star has stayed Black-owned and independently run. We didn't get here by waiting on ad budgets that were never built to prioritize us. Our readers did that.

Corporate support for Black media has always been thin. Outlets like ours get roughly 1% of the $170 billion spent on U.S. advertising each year, and that margin is shrinking further as advertisers walk back the DEI-linked commitments they made in 2020. That's the backdrop. It's not why we're asking.

The wider picture isn't any steadier. Newspaper ad revenue has fallen more than 80% since 2005, and local newsrooms are closing at a rate of roughly two a week nationwide. When outlets go under, it's rarely the ones built to center a Black perspective from the ground up that get to stick around.

We know a request for support isn't why you came here. But without readers choosing to fund this work directly, the depth of reporting we can do at home and abroad shrinks along with everyone else's. If you're not in a position to give, that doesn't change how much we value you as a reader.

If you are able to, a recurring contribution does more for us than a single one-time gift, because it lets us plan the next investigation instead of just the next invoice. It takes about 30 seconds, no long form, no account. Thank you for continuing to support independent journalism and freedom of the press.

Back to top