Deepwells was built in approximately 1845 for Joel L.G. Smith (1819-1875), a descendant of Richard “Bull” Smith, founder of Smithtown. He bought the Deepwells property from Gamaliel Taylor, who was also a member of the Smith family. The property was a working farm of just under 50 acres, bisected by North Country Road. There were several out buildings, including barns and other structures, on the property which are no longer existing. There are a few buildings that remain standing including a small frame well house and a laundry garage built in the nineteenth century, as well as the Caretakers House located on the corner of Moriches and North Country Road. The Caretakers House is now owned by the Village of Head of The Harbor.
Joel Smith did not live at Deepwells long. The name of George Pullis appears on a property map in 1858. Milton H. Smith acquired the property before 1873 and Clinton Smith, Secretary of the New York City Parks Department, inherited the estate.
William J. Gaynor, Mayor of New York City from 1910 to 1913, bought Deepwells in 1905 after renting it from Clinton Smith. Gaynor was particularly enthusiastic about pigs and he raised them at Deepwells. Tradition has it that Mayor Gaynor named the estate “Deepwells,” after the two brick-lined, 125-foot wells on the property.
Winthrop Taylor bought the house from the Gaynor estate in 1924 after first renting it for about four years. The architectural firm of Peabody, Wilson & Brown undertook major renovations on Deepwells on or after 1924. The two south side parlors were turned into one large room and the blind window was opened up. The rear porch was extended, and the rear windows in this room were converted to French doors. It is possible that the firm performed other renovations as well. During Taylor’s residency the laundry house was turned into a garage. The rear was extended and doors were installed in front, while the wooden floor and steps of the front porch were replaced with bluestone. Winthrop Taylor was careful in his renovations and often reused existing material or made replacements which matched the original elements. Taylor, like Joel Smith and William Gaynor, was committed to maintaining the Deepwells property as a working farm. Unlike Mayor Gaynor, Taylor’s interest was cows rather than pigs and he was well-known for his dairy farm. His Ayrshire herd was given up before World War II and the barn and milk house burned in 1956.
Winthrop Taylor’s son Jeremy inherited the property in 1975 and sold it to a developer. Suffolk County acquired the house and part of the property in 1989. The rest of the farm site is in private hands except for a five acre parcel containing the Caretaker’s Cottage, which is owned by the Village of Head of the Harbor.
Deepwells is an example of Greek revival architecture. It is listed in the National Register of Historic Places and is dedicated to the Suffolk County Historic Trust.
The St. James General Store, run by Friends for Long Island Heritage, was purchased by the County and added to this park in 1990.