It was the home of the American author Washington Irving, best known for his short stories, such as "Rip Van Winkle" (1819) and "The Legend of Sleepy Hollow" (1820).

Among other buildings, Wolfert's Roost contained a simple two-room stone tenant farmhouse,[5] built about 1650.

[7] Irving would immortalize the Van Tassel family name in his short story "The Legend of Sleepy Hollow" (1820).

[9] Irving had recently undertaken a substantial trip through the prairies of the Arkansas and Mississippi Rivers, and the frontier lifestyle made him lament his lack of a home of his own.

"[7] Irving requested that his friend and neighbor, English-born painter George Harvey,[13] become his aesthetic collaborator and foreman in the house's subsequent remodeling and enlargement, and the landscaping of the grounds in Romantic style, which included creating a pond Irving called "The Little Mediterranean", with a waterfall that led to a babbling serpentine brook.

[5] Oliver Wendell Holmes Sr. said that Sunnyside stood "next to Mount Vernon, the best known and most cherished of all the dwellings in our land.

He left Sunnyside in the care of his brother Ebenezer, who lived there with his four grown daughters, who supervised the running of the household.

A replica of the house stands at Liberty Square at The Walt Disney World Resort's Magic Kingdom; the building serves as a quick service restaurant.