Estate of Oleg Cassini, Jackie Kennedy’s Favorite Designer, on Market for $19.5 Million

Oleg Cassini’s Oyster Bay estate. Photo: Courtesy of Laffey Real Estate

To picture the recently listed estate of Oleg Cassini, famed couturier to Jacqueline Kennedy, think Gatsby. Now on the market for $19.5 million, the lavish, Italian Renaissance–style mansion was perfectly suited to the designer, socialite, and playboy. In his final years, he shared it with the woman he had discretely married three decades prior, Marianne Nestor.

The Russian-born designer became colloquially known as “Secretary of Style” when he accepted a position as Kennedy’s personal couturier. He designed the gown that she wore to her husband’s Inaugural Gala, a deceptively simple ivory piece that would later rank among the London Design Museum’s “50 Dresses That Changed the World.”

Jackie Kennedy in a dress by Oleg Cassini with President John F. Kennedy (and Lyndon Johnson standing behind them) and French Minister of Cultural Affairs Andre Malraux before the May 1962 dinner. Photo: Abbie Rowe, White House/John F. Kennedy Presidential Library and Museum

The fashionable first lady’s wardrobe of timeless dresses and pillbox hats was soon copied the world over, and Cassini, the visionary behind its explosive popularity, became a celebrity in his own right.

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Until Cassini’s death in 2006, the mansion was a stunning country retreat for the couple. Inside, exquisite moldings span 35 rooms, including 14 bedrooms and eight and a half bathrooms, and the property includes a pool, cabana, pond, and tennis court—Cassini’s sport of choice since youth, which frequently resulted in screaming matches between Cassini and his younger brother, Igor. A financial feud among the designer’s surviving relatives is reducing the breathtaking property to legal collateral.

Nestor was arrested on May 3 over mismanagement of the $55 million in her late husband’s will, as a result of which the estate has been listed in a court-ordered sale.

A corridor looks into the yard. Photo: Courtesy of Laffey Real Estate

Detailed millwork recalls an era of extravagance gone by. Photo: Laffey Real Estate

A sitting room. Photo: Courtesy of Laffey Real Estate

One of the estate’s eight bathrooms. Photo: Courtesy of Laffey Real Estate