Postilio was a founding member of CORE, a New York real estate firm, and has been ranked as one of the top real estate agents in New York City. He entered the real estate profession in 2003 at the suggestion of a friend. He was hired by Shaun Osher of Douglas Elliman, the largest residential real estate brokerage in the New York metropolitan area. In 2005, Postilio and Osher left Elliman to start a new real estate brokerage, which would become CORE. In 2015, Postilio and his partner Mickey Conlon joined Douglas Elliman, the No. 1 real estate brokerage in New York. Company chairman Howard Lorber stated that, "Tom & Mickey are two of the brightest superstars in the business," with company president and CEO Dottie Herman adding they were, "well-respected for their collective experience, trusted business relationships and cultural and social influences, Tom and Mickey are true leaders in their field." Postilio was ranked among the top 1000 Real Estate Professionals in the United States by REAL Trends/The Wall Street Journal. Postilio is known for working with high-net-worth celebrity clients such as Jim Carrey, Joan Collins, Michael Feinstein, Lady Gaga, and David Sanborn. He became a star on Selling New York, a reality show on HGTV that features brokers selling high-end real estate to some of New York's wealthiest residents. He frequently appears alongside his partner, Mickey Conlon, and the duo have been dubbed the show's "Dream Team." Responsible for more than $1.5 billion in residential sales, they rank among the most successful real estate brokers in the United States and were named CORE's top-producing agents in 2013 and 2014. Postilio has appeared on numerous television shows as a real estate commentator and host, including CBS's Living Large, Fox's Good Day New York, NBC's Open House, ABC's Good Morning America, and CNBC's Mega Homes Report. He has also been featured in articles in several publications, including The New York Times, New York Daily News, the New York Post, the Wall Street Journal, Forbes, The Hollywood Reporter, and a variety of real estate trade publications. Postilio has been designated a Certified Negotiations Expert by the Real Estate Board of New York, of which he is a member. He was appointed as a juror for the Architzer A+ Awards, the world's largest architectural awards program. After Donald Trump announced he would run for president, Postilio appeared with Conlon on Inside Edition to discuss Trump's first mansion in Greenwich, Connecticut, which was listed for $54 million, $50 million more than Trump paid for the estate when he bought it in 1982. In 2007, Postilio was at the center of a story that made international headlines about the astronomical pricing for parking spaces in New York City. Based on the sale and waiting list for parking spaces in the basement of a boutique luxury condominium project at 246 West 17th Street in Manhattan's pricey Chelsea neighborhood, the record price tags of $275,000 were compared to the cost of cars, home values, and income levels around the world. Still, the cost of such spaces was justified as valuable by residents and industry economists based on the lack of available parking in the city and a decline in the number of parking garages in New York City. As of late 2014, prices for some parking spaced in Manhattan have exceeded $1 million.
Singing career
Before getting involved in real estate, Postilio began his career as a singer of the Great American Songbook and traveled internationally with the Glenn Miller Orchestra. He traveled with the group for one year, playing in venues in Europe, Asia and the United States. He received a MAC Award for Outstanding New York Debut as well as the Backstage Bistro Award for Outstanding Vocalist. Postilio sang in the Oak Room at New York's Algonquin Hotel and was noted for his Frank Sinatra singing style, with the New York Times stating "his carefully syncopated phrasing and exuberance suggest a softened echo of the late-50s Sinatra in his swinging mode." He released two albums in the 1990s: What Matters Most and Dream. Upon seeing his performance in 1998, Regis Philbin stated on ABC TV's Regis & Kathie Lee, "he looks and sounds like a young Sinatra." His acclaim as a Sinatra-style singer led to his starring role in the Off-Broadway musical, Our Sinatra. He has appeared on The Today Show, PBS Great Performances, Showbiz Tonight, and BBC News. Postilio returned to the nightclub stage in 2011 with his show "This Time Around", performed at Feinstein's at Loews Regency in New York.
