Born into a wealthy New York family that boasted several accomplished female artists among its ranks, Rosina Emmet Sherwood received her first instruction from her mother. Like many of her generation, Julia Pierson Emmet believed that drawing was the symbol of a well-bred woman, and each of her three daughters rose to artistic acclaim. At the age of thirteen, Rosina successfully submitted an unsolicited sketch to a magazine, for which she was duly compensated. Early in her career, she illustrated books, periodicals, and stories—some of which she wrote herself—and in 1880 won one thousand dollars from the Louis Prang & Co. for Christmas card designs. At the same time, she regularly exhibited her paintings at notable venues and did numerous pastel portraits of family and friends. 

On a largely sightseeing trip to Paris and England in 1876–1877, Rosina Emmet was presented at court to Queen Victoria. Back in New York, she joined Associated Artists, a design firm that produced tapestries, curtains, and wallpapers. Between 1878 and 1880, she was one of William Merritt Chase’s first private students in his Tenth Street Studio, and shortly afterward opened her own studio in the building. She returned to Europe in 1884 for a six-month-long period of study at the Académie Julian; while there, she made copies in the Louvre and traveled to Barbizon, a destination made famous by French landscapists. During the 1890s, she assisted Chase in the establishment of his Shinnecock Summer School of Art on Long Island, serving as a member of the executive committee.

In 1881, Sherwood exhibited three portraits at the National Academy of Design and ultimately was elected to the rank of Associate in 1906. Despite marriage in 1887 and the subsequent arrival of five children, she maintained a relatively active schedule exhibiting at prominent commercial galleries and prestigious museums, including a one-artist presentation at New York’s distinguished Macbeth Gallery, the first to exhibit American art. In 1893, she was commissioned to create a mural personifying art, music, and motherhood for the library of the Woman’s Building at the World’s Columbian Exposition in Chicago.

Sherwood spent the winter of 1918–1919 in Savannah, Georgia, where her son was convalescing from war injuries. In 1922, she embarked on a trip around the world, recording many of the scenes she encountered in watercolor. While much of Sherwood’s work is held in private collections, she is represented in the holdings of the Smithsonian American Art Museum.