The documented history of the land comprising the York Harbor Inn complex begins on October 9, 1762, when Abiel Goodwin willed the land to Mary Goodwin, and for the next 139 years it remained in the hands of Goodwin heirs. As York grew in importance as a summer vacation destination in the late 19th century, the land’s use changed. In 1870 Charles Goodwin built a boarding house called the Goodwin House where the York Harbor Inn parking lot is today; in the 1880s it was enlarged and became the York Harbor Hotel, and after William Varrel purchased it in 1894 he renamed it the Yorkshire Inn. An annex was added late in the 19th century, and sometime in the mid 20th century the Yorkshire Inn was demolished. In 1894 Hartley Mason expanded his Mason Hill development by purchasing property on the north side of York Street from William Varrel and Charles Goodwin, later building a Mission Revival structure known as the Stucco Shop as well as a separate building that housed the Frank Brothers Bootery. Behind the Bootery and the Half House stood an older house called Shadyside, of undocumented origin, which for much of the mid 20th century was occupied by Albert Newick, Hartley Mason’s estate manager, and his family as part of the Mason estate. The Half House, originally the Mason-Varrel cottage, dates to about 1865 and took its later name from its early use as a two-family house with two owners and a property line running down the middle. George Donnell built it on land purchased from William Donnell, and in the 1890s it was shared by William G. Varnell and Hartley Mason; Mason bought his half in 1894 for Nathan W. Goodwin, while deed records do not show when or how Varrell obtained his half. In 1984 Joseph Dominguez bought the Varrell side from Mrs. Lord, née Varrell, who had inherited it from her parents, and in 1978 the Dominguez family acquired all remaining Hartley Mason estate land on the north side of York Street. The building that became the York Harbor Inn was purchased in 1901 by the York Harbor Reading Room and served as its meeting place until the end of 1907. For the next eleven years it belonged to Willard J. Simpson and operated as an inn. In 1918 Simpson sold it to Florence M. Horne, who ran it as the Hillcroft Inn; during her ownership the building was turned to face the ocean and a porch was added, later enclosed in the 1930s or 1940s to enlarge the dining room, while a one-and-a-half-story addition enclosed the original post-and-beam structure on the York Street side. A rumor held that this addition stood above a 17th-century room floated from the Isle of Shoals during the Revolutionary War. In 1947 Louise Sawyer and Mary A. Colligan bought the property and renamed it the Colligan Inn, which remained in the Colligan family until December 14, 1979, when Joseph T. Dominguez purchased it. The Dominguez family then expanded the inn to the rear with additional dining and meeting spaces.