Broadcaster Colin Cowherd Buys Another Chicago Luxury Home

Fox Sports broadcaster Colin Cowherd has added a 7,500-square-foot estate in Winnetka to his growing Chicago real estate portfolio.

Cowherd, and his wife, Ann purchased the five-bedroom home at 901 Hill Road for about $593 per square foot, Crain’s reported. The couple finalized the purchase on Dec. 9, securing the property for $4.45 million, or 81 percent of the initial asking price.

The sellers, Erin and Scott Dickes, listed the home in March at nearly $5.5 million, but after multiple price adjustments, sold it for about $1 million less. Annie Flanagan of @properties Christie’s International Real Estate represented the Cowherds, and Compass broker Chris Downey represented the sellers.

The Cowherds also bought a condo on the 25th floor of the 70-story Park Tower building, on North Michigan Avenue, for $3.25 million last January. Their primary residence is in California, and it’s unclear what connection they have to the Windy City.

Beyond Illinois, the Cowherds also own an $8.5 million Rhode Island property on the same street as Taylor Swift’s mansion.

Winnetka recorded 99 sales of $4 million or more this year, which falls short of 2022’s peak of 136 sales, but it highlights the continued demand for luxury properties in the area.

Recent luxury sales in Winnetka include the 11,250-square-foot home of Chicago Cubs pitcher Kerry Wood for $8.5 million, and the iconic “Home Alone” property on Lincoln Avenue for $5.25 million.

High-end listings include the $35 million estate of a retired Goldman Sachs executive — the most-expensive listing in Illinois — and a $16 million lakefront mansion on Sheridan Road.

— Andrew Terrell