The children, known as the "Astor Orphans", were raised at their parents' estate in Rokeby, New York, built by John Armstrong Jr., his mother's great-grandfather.

[8] John Winthrop Chanler's will provided $20,000 a year for each child for life (equivalent to $470,563 in 2018 dollars), enough to live comfortably by the standards of the time.

[9] Winthrop himself inherited all of his father's personal property in his New York City home, located at 192 Madison Avenue, all of his real estate in Delaware County, and a house on Cliff Lawn in Newport.

[1][12] While at Harvard, Winthrop was part of a prank played on Oscar Wilde when he appeared before the College to give a speech at the Boston Music Hall in 1882.

[4] Chanler, along with 60 other Harvard students, "marched down the center aisle in pairs, all carrying sunflowers and wearing Wildean costumes of knee breeches, black stockings, wide-spreading cravats, and shoulder length wigs.

"[4] His great-aunt Julia Ward Howe, who considered Winthrop her favorite, was in the audience and was apparently aghast at the prank.

[16][17] After his marriage, the Chanlers moved to Washington, D.C., where they surrounded themselves with a group of friends including Theodore Roosevelt, who was then the Civil Service Commissioner, and later President of the United States.

[22] By the time his arm healed, the war was over, so Chanler sailed to Europe where he stayed for several years in Sorrento, Italy[12] taking a "life of hunting.

[18] Thereafter, they moved to Tuxedo Park, New York which according to his wife, "seemed dull in its exclusiveness; the tendency of Anglo-Saxons to separate into 'social sets and hierarchies' was in striking contrast to the hospitality and cosmopolitanism of Roman society" where she had grown up.

He reportedly spent most of his time fox hunting and horse breeding at his estate, Sweet Briar Farms,[1] which was once owned by the Wadsworth family.