5. Winfeld Hall, Woolworth Mansion

Winfield Hall aerial view.Photo courtesy of Max Spann Real Estate & Auction Company.

Also located at Glen Cove, the historic Woolworth Estate, also known as Winfield Hall, was designed in 1916 by acclaimed architect C. P. H Gilbert for the prominent department store owner Frank Winfield Woolworth. Construction of the Italian Renaissance style home was commenced immediately after Woolworth’s prior home–located at the same site–was destroyed in a mysterious fire. Fortunately, the plans for the new mansion were already drawn.

After Woolworth’s death, the estate loitered in the family until 1929 when it was purchased by the wife of Richard S. Reynolds, of the R. S Reynolds Metal Company. Afterwards, the mansion became the Grace Downs Academy, a business school for young women, until it was purchased by Martin Carey, the brother of former New York Governor Hugh Carey.

In late-January, 2015 a fire broke out at Winfield Hall that extensively damaged the mansion. Ironically, after the original fire of 1916, Woolworth built the new estate to be fireproof. According the North Shore historian Paul Mateyunas, the cost of rebuilding the house would run the tens of millions of dollars.