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In the late 1600s, the land that is now Deep Cut Park was bordered Middletown Village, the heart of Monmouth County's first European settlement. By 1668, the village had been laid out into thirty-six "home lots" along a Lenape trail path that later became Kings Highway. These lots were used as family farms and passed down through the families until 1890. In 1890, the sheriff took over the current Deep Cut property for taxes, and after several interim owners, the 35+ acres were sold to Edward and Teresa R. Dangler.

In 1928, the Danglers constructed a large two-story Colonial Revival Mansion on the hilltop. Then, in 1935, Vito Genovese purchased the property and re-fashioned the grounds in a pseudo-Italian style reminiscent of Naples, Italy, where he was born. Caruso Construction Company of Atlantic Highlands carried out the construction and Lovett's Nursery of Little Silver planted the gardens according to the plans of Theodore Stout.

Stout, who wanted to create "something big enough to make an impression from the top of the hill," was given free reign in designing the garden. Mr. Genovese's only requirement was the Mt. Vesuvius rockery. Since the Colonial revival mansion did not lend itself to an Italian garden and there was adequate water for the terraced water pools of traditional Italian gardens, the design was a mixture of English and Italian styles. Features included a pseudo-Italian rock garden on the steep slope below the house, terraced gardens at the foot of the hill, large recessed rectangular garden area surrounded by a low stone wall, and a masonry pergola which is still stands.

In 1937, Genovese left the country, ending the project prematurely. In that same year, an unexplained fire destroyed the mansion. In 1948, the property was sold to Dominic Caruso who conveyed it in later years to Mary Gladys Cubbage. On December 31, 1953, Karl and Marjorie Sperry Wihtol purchased "Deep Cut Farm" and erected the existing house to replace the one that had burned down. The Wihtols also renovated the greenhouse and worked on the gardens.
 
Karl Wihtol died in 1970, and Marjorie resided at Deep Cut Farm until 1977. In her last will and testament, she donated half the property to the Monmouth County Park System, to "be used for park and horticultural purposes only." The Park System purchased the rest of the property with the New Jersey Green Acres funds.

On December 29, 1977, Monmouth County took the title of the 39.09 acre Deep Cut Farm. The park was dedicated September 14, 1978 as a facility devoted to the education and enjoyment of the home gardener. The Monmouth County Park System had added acreage over the years. Currently, Deep Cut Gardens consists of 54 acres.