The penthouse’s interior in all its splendor

LIST PRICE: $5.75 million

The marvelous view across Lincoln Park to Lake Michigan has not changed much since 1927, when this two-story apartment atop a then-new 18-story co-op building became the masterfully designed home of Charles and Elizabeth “Bobsy” Goodspeed.

Key rooms in the Goodspeeds’ apartment, originally designed by the architect David Adler, have changed little, too, although they have been updated with contemporary mechanical systems. The quatrefoil-shaped nickel inlays in the ebonized wood dining room floor, the carved eagle that crowns an old English mantelpiece pediment, and even the door concealed in library paneling that opens to a small powder room are all intact and recently restored.

It’s always nice to see a home’s historical look preserved, but it’s particularly gratifying when the space has hosted the likes of Gertrude Stein, George Gershwin, and Thornton Wilder. (In Chicago’s October 2008 issue, Geoffrey Johnson’s Portrait of a Lady described Bobsy Goodspeed’s tenure as a doyenne of Chicago’s arts and society scenes.) Like the former Goodspeed home, most units in the building, which was designed by the architect Andrew Rebori, are spread across two floors, with large windows in the main rooms and smaller windows in the upstairs bedrooms.

For the last 11 years, the Goodspeeds’ 5,600-square-foot half-floor apartment has been the home of a man closely associated with a latter-day Chicago doyenne: Oprah Winfrey. Jeff Jacobs, who was the president of Winfrey’s Harpo Entertainment for 18 years, and his wife, Hollye, bought the 13-room apartment in 1999. (Because the building is a co-op, public records do not reveal how much the couple paid; neither Jacobs nor the home’s listing agent, Janet Owen of Sudler Sotheby’s, would disclose the price.) “It was a home in the sky with beautiful bones and a great pedigree,” Jeff Jacobs wrote me in an e-mail. Jacobs left Harpo in 2004 and is now a private investor. He and his family are moving out of state.

The apartment was not at its best when the couple bought the place. The mahogany paneling in the library had been painted over, and a suite of servants’ quarters and workrooms at the back of the main floor had become obsolete. The Jacobses oversaw a complete restoration that included converting the servants’ spaces into a large kitchen, a breakfast room, and a family room, the latter with a beamed ceiling and rich paneling that evokes the original Adler rooms.

“Scott Himmel, our designer, kept all the Adler features but made it a comfortable home to raise a family,” Jacobs wrote. Himmel’s work included laying new wood flooring in the living room and creating a modern master bathroom in what had been a bedroom. The extra-large closet in another bedroom suite is now a cozy sleeping room, while the bedroom itself is a children’s playroom. (The home has a total of four bedrooms.) That suite and the master bedroom face Lake Michigan, and Jacobs wrote that he and his wife have enjoyed “sunrise every morning over the lake and the park.” As Janet Owen points out, there are views in all four directions from one room or another.

Those views, along with the home’s many architectural assets—including a sinuous staircase beneath a large skylight and arched interior doorways—make this, as Owen puts it, “a superb modern family home with all the grandeur that it originally had.”

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Photograph: Courtesy of Sudler Sotheby’s International Realty