I
n this episode of Barons of Broadway, we explore the history of Defendorf Lane at 539 North Broadway in Upper Nyack, named after Civil War Captain Wilson Defendorf. A wealthy real estate developer, Defendorf bought and expanded Major John Smith's cottage near the onset of the Civil War. He later served as a volunteer troops captain in Virginia and was declared the richest man in Rockland County at the time of his death.

    The house on Defendorf Lane changed hands several times after Defendorf's wife passed away. In 1933, Helen Hayes considered it for her Nyack residence but ultimately chose Pretty Penny instead. Judge John J. Reilly lived there for 40 years before it was demolished in 1997 to make way for three riverfront estates.

    Wilson Defendorf was born in Pennsylvania in 1820 and became a stepchild after his father's death. His mother remarried Jesse Blackfan, who served as Surveyor General for Tennessee under President Andrew Jackson. Defendorf earned an appointment to West Point in 1835 but left the academy before graduating. He later raised a company of volunteer troops during the Civil War.

    Defendorf purchased the Smith house in 1862 and expanded it with a large addition while he was away at war. After the war, he became a successful real estate investment broker and owned several buildings in New York City. Defendorf married Mary Roche in 1864 and distributed produce and goods to New York City from Van Houten's Landing.

    In 1883, Defendorf purchased an additional 14 acres of riverfront property, including the old quarry surrounding the Smith house. He also bought a second property on North Broadway and Third Avenue, which was demolished in the 1930s. Defendorf passed away in 1891, leaving an estate valued at $400,000.

    The estate passed to Defendorf's great-nephew, John J. Reilly, who lived in the house for many years. Reilly was a lawyer and served as a judge on the New York Supreme Court. He preserved much of Defendorf's furniture and historical items, including his battle flag and discharge certificate signed by General Ulysses S. Grant.

    Today, real estate baron Wilson Defendorf is mostly remembered for his namesake, Defendorf Lane. The old Smith cottage didn't survive beyond the Reillys and was demolished in 1997 to make way for three contemporary houses.