Jason Halpern is a developer and his career in real estate is balanced by fatherhood. He began his career at Halpern Enterprises a firm located in Winchester and was founded by his late father although it was Jason who launched it back in the late 1990s. His father was a national champion in offshore powerboat racing and died in a boating accident in the year 1981. In the late 1990s, the company was sold to Reckson Associates. Halpern has a teenage son known as Max from his previous marriage. They have a good father-son relationship, and Jason has taken him to watch their family long term team, New York Giants while playing across the country. This includes the day the team won the 2012 super bowl in Indianapolis. The two love scuba diving for they have been spotted doing it on various occasions.
His father sponsored a racing team that was named after his company in the late 1970s. Jason has inherited the love for fast cars from his father and in the early 2000s; he participated in a racing competition. Before his recession, he had planned to take part in races and had already purchased a car and commenced training. The reasons that he quit is due to his work getting hectic. He has stated that he would like to get back to the sport in the future.
Halpern got engaged to a Ukrainian model Veronika a few years ago, and the two have traveled together in places such as Africa to celebrate the 40th birthday of their close friend Winston Fisher who is a developer too. He is recognized to be a fan of luxurious watches, and among the many, he owns a Vintage Patek although it first belonged to his father. He has kept it to date and has high regards for it.