Before Walter T. Shirley came on the scene and carved up the Mastic Peninsula into small lots, there was Edward R. Tolfree in the early 1920s, who also harbored the dream of turning his 1,200 acres into a new waterfront community. His interest in the area died with the untimely passing of his wife, a famed writer, and the local chronicle picks up again with the Prudenti Family and storied history of the Island View Manor.
Tolfree was a chemist who worked with the DuPonts, helping develop many of the products that are still around today. The family had bought the Masury Estate in Center Moriches and suggested the purchase of the waterfront property, running from Neighborhood Road to Smith Point, to Tolfree, one of their top executives. The chemist and his wife, who went under the pen name Aline Gorren, moved into a spacious manor house on the property, where they would throw lavish parties. After Aline’s death, Tolfree abandoned the house, which still sits on Manor Lane off William Floyd Parkway.
A pilot during World War 1 stationed at Camp Upton, Shirley flew out of an airstrip at what is now Shirley Beach. He fell in love with the area and bought the Manor House in 1945. The man who would build out vast parts of the area that now bears his name started out as a promoter. It wasn’t until he went into the attic one day that he found the plans to develop the community right down to the names of the streets. They were drawn by a previous owner, Fred Quimby, and had inspired Tolfree until the fate of Aline Gorren intervened. Equally inspired, Shirley sold the Manor House to raise cash for his development dream and went on to build the thousands of homes that make up the community as it is today.
The new owners of the mansion were Dana and Rex Cutro, who convinced his sisters to relocate from Hazleton, Pa. to begin a new life on Long Island. “At the urging of Walter T. Shirley, who needed a place for his prospective homebuyers to stay, my grandmother, Angela, started the Shirley Motel,” explained Center Moriches attorney John Scott Prudenti. “Angela and her sister came here in their fifties and started entirely new careers, creating the Island View Manor and then the motel as one of the area’s first resorts with entertainment from a young Tony Bennett and the Dorsey Brothers,” he said, noting that his father and uncle also played a key role in developing the area. “My uncle Anthony needed an attorney, and that’s why my father went to law school,” Prudenti said. “They were responsible for building hundreds of homes in the area as well, along with a number of commercial properties.”
Anthony Prudenti also had a successful career in politics, having served as chairman of the Suffolk GOP. His daughter, A. Gail Prudenti, was Suffolk’s Surrogate Judge and was in charge of the state court system under two different governors. Her first name comes from her grandmother, Angela, a leading businesswoman of her time. Rex and Dana’s son, Rocky, was a top musician of the era, a musical tradition that followed to John Scott Prudenti, who also worked in the profession before embarking on a long career in the Suffolk District Attorney’s Office.
An interesting side story is told by John Scott regarding the source of funding that went to Shirley for the sale of the former Tolfree House. “My great uncle was severely injured in a coal mine collapse. He was trapped for three days, and his leg was left shorter than the other. The miners had recently unionized, and his settlement was one of the first under the new agreement,” Prudenti explained. “Cash from that accident set a course of destiny that changed my family's history and the trajectory of this community.”