Born in Łódź, Poland, to a Jewish family, Winter emigrated in 1901 to New York City, one year after his father. His father took on a tour of Manhattan, showing him the lavish Vanderbilt and Astor houses which Winter was to eventually own. After saving for 12 years, Winter in 1912 used the proceeds as a painter of tenements to buy tenements in lower Manhattan. The following year, he and Scotch-Irishman Andrew O'Brien bought their first apartment building, in Washington Heights. The venture was successful and Winter soon after started his own company funded by his share of the profits and investors in the Polish Jewish community, he invested in mid-Manhattan where he targeted the great mansions of Fifth Avenue for redevelopment. In 1925, he purchased the Mrs. William B. Astor House and later demolished it; in 1929, it was replaced with the new Congregation Emanu-El of New York. Also in 1925, he purchased the William K. Vanderbilt House and demolished it replacing it with a residential high rise. By tearing down the mansions, Winter along with fellow real estate speculatorFrederick Brown, were credited with transforming that section of Fifth Avenue into "the aristocrat of shopping thoroughfares." In 1927, he formed Winter Incorporated and offered preferred shares on the New York Stock Exchange which enabled him to raise funds for larger projects. He went bankrupt in 1937 during the Great Depression losing his entire $40 million in wealth, although he recovered most of his wealth by his death in 1944. He was known for having the ability to identify under-valued properties in up-and-coming neighborhoods, making a purchase, and then selling them later for a tidy profit. Within 20 years, he became the most prolific realtor in New York City with over $500 million sales. His portfolio of prominent properties came to include the Hotel Delmonico, the Stanhope Hotel, the Hotel Lenori, the Spanish Flats, Bretton Hall, the Gunther Building, the Hotel Claridge, Hotel Hermitage, and many residential properties along Park and Fifth Avenues.
Personal life
He was married to Dora Winter; they had five children: Benjamin Winter Jr., Marvin S. Winter, Beatrice Winter Spitz, Ethel Winter Schanzer, and Natalie Winter Ballen. In the 1950s, his son Marvin turned the company from an opportunistic buyer and seller of real estate to a long-term holder. After Marvin's death, his sons Benjamin Winter and James Winter took over the family business. Later, Benjamin's son, David S. Winter, joined the business.
