In 1901, Ripley had commissioned Warren & Wetmore them a 35-wide mansion in New York's Upper East Side at 16 East 79th Street. The five-story brick-and-limestone Georgian home, that featured a columned portico and two-step porch, was completed shortly before his death in 1905. In 1912, his widow sold their New York City residence, which was described by "The New York Times" as the "dwelling occupies a plot 35 by 102.2 feet in the choicest upper Fifth Avenue residential section", for $400,000. After she sold the residence, she moved to 101 East 72nd Street. On October 14, 1885, Ripley was married to Mary Baldwin Hyde (1867–1938). Mary was the daughter of Henry Baldwin Hyde, the founder of Equitable Life Assurance, and Annie (née Fitch) Hyde, and the sister of James Hazen Hyde. Together, they were the parents of:   In 1895, Ripley and James Lorillard Kernochan (son of James Powell Kernochan) were arrested in Hempstead for playing golf, on a Sunday, on the greens opposite the clubhouse at the Meadow Brook Hunt Club. In 1899, he urged his brother, Harry Dillon Ripley, to take charge of his financial affairs after Hyde had run into debt of $100,000. Just before Ripley died, Harry sued Sidney and the Knickerbocker Trust Company alleging "misconduct in managing his property." After his death, the Supreme Court of New York Referee conducted an investigation and found that "the trust had been well and faithfully administered" and Sidney and the Knickerbocker Trust were exonerated and relieved of their duties. Ripley died of appendicitis on February 24, 1905. His will was quickly probated and his estate, valued in excess of $5,000,000, was left to his family. His wife received their Long Island home, and all "jewelry, horses, carriages, and harness, and all property of the deceased for life." All of the funds in trust he inherited from his grandfather passed to his children. His wife received $848,505 and each of his children received $74,614 directly. After his death, his widow remarried to Charles R. Scott, a Hong Kong-based British banker who was the son of Col. Robert Scott of the Irish Fusiliers, in Bar Harbor, Maine in 1912.