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

Sumptuous mansions, extravagant parties, lavish outfits, and exotic cars characterize some of the scenes portrayed by F. Scott Fitzgerald in his book The Great Gatsby about the Gold Coast of Long Island during the 1920s. Inspired by visits to Long Island, Fitzgerald’s book takes place in an era when wealthy New Yorkers, seeking a more bucolic retreat from their urban lives, built opulent estates on the north shore of Long Island. Of the grand Gold Coast mansions of that era that remain today, many have been demolished but many others have been re-purposed and renovated, functioning as venues for special events and weddings. Others have been converted into educational centers and museums. Here are ten of these grand mansions from Long Island’s Gold Coast era.

1. Oheka Castle

Oheka Castle, one of the notable Gold Coast mansions
Oheka castle features an expansive garden, Courtesy of Oheka Castle.

Oheka Castle, also called the Otto Kahn Estate, was built during the 1910s by philanthropist and investment financier Otto Hermann Kahn. Situated on the highest point on Long Island in Cold Spring Harbor, the estate is the second-largest private home in the United States boasting 127 rooms and over 109,000 square feet. The estate also features an 18-hole golf course, one of the largest private greenhouse complexes in America, and a sprawling French Formal Garden in the front of the house. Oheka Castle exemplifies the estates of the Jazz Age, also known as the roaring ’20s, and is said to have served as a partial inspiration for Gatsby’s estate in F. Scott Fitzgerald’s The Great Gatsby.

During the heydays of the Gold Coast of Long Island during the 1920s, Kahn used the lavish estate to host extravagant parties and entertain royalty, heads of state, and Hollywood stars. After Kahn’s death in 1934, the Gold Coast estate changed hands multiple times and was utilized for various purposes, including a retreat for New York City Sanitation workers. From 1948 to 1979, the Eastern Military Academy used it as a school. Today, Long Island developer Gary Melius operates it as a weddings and events venue, luxury hotel, and conference center.