The Chatsworth has been part of the Upper West Side skyline for more than a century. Completed in 1904 just steps from Riverside Park, the landmarked Beaux Arts building is one of those classic New York addresses that feels tied to another era, with its stately limestone facade embellished with carved cherubs and decorative shields and capped by a towering mansard roof. Over the years, it has drawn its share of notable residents, including Susan Sarandon, while Conan O’Brien reportedly once lived in one of the building’s penthouses before the upper floors were reimagined.

Today, the building’s crown looks very different from anything its original architects could have imagined. Spanning the top two floors, Penthouse E brings a sleek, modern sensibility to one of the Upper West Side’s most historic addresses. The duplex, now on the market for $21.95 million with Kathy Murray of Corcoran, extends across 6,000 square feet, with an additional 3,700 square feet of private rooftop terrace space.

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What stands out is the contrast. From the street, the Chatsworth is unmistakably prewar. Upstairs, the home feels bright, open, and decidedly contemporary. Soft neutral tones, custom millwork, and wide-plank oak floors give the interiors a calm, understated feel that not only lets the views take center stage but also provides a clean canvas for further customization, while the multi-level terraces are outfitted with a motorized pergola, outdoor kitchen, and multiple spots for dining and relaxing above the city.

The main entertaining level revolves around a 30-foot-long great room, where oversized windows set into the sloped ceiling frames views of Riverside Park, the Hudson River, and the Manhattan skyline. The kitchen opens directly onto one of several terraces, creating an easy indoor-outdoor flow that feels more akin to a suburban home than a New York apartment, as does a library with a wet bar and attached bath.

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The lower level houses the sleeping quarters: five en suite bedrooms anchored by a spacious primary suite with dual marble bathrooms and multiple walk-in closets. A den with a wet bar adds a secondary gathering spot.

The listing arrives as demand for trophy homes on the Upper West Side remains strong. Just a few blocks away, the sprawling mansion at 48-50 West 69th Street recently entered contract with an $85 million asking price, a deal that could set a new neighborhood record if it closes near the ask, according to the New York Post.

Click here to see more photos of the duplex penthouse at The Chatsworth.