Once there, it has been claimed a man approached them to ask for the time, before pulling out a gun and pointing it directly at Jonathan's mother's head.
Jonathan - who is also known as Foodgod - then told the man to take whatever he wanted, and he ended up grabbing the Richard Mille watch.
There was also allegedly a second gunman on the scene who was keeping watch, and both perpetrators are believed to have fled on foot when neighbours came out to see what was going on.
Englewood Cliffs police told TMZ officers were on the scene within a minute of the call to get a description of the suspects, and although a K9 unit was used to track the suspects and potential evidence, the search is yet to yield any results.
The scary incident comes almost four years after Jonathan's best friend Kim, 39, was robbed at gunpoint in Paris, France, in October 2016.
Five gunmen posed as police officers to break into the 'Keeping Up with the Kardashians' star's hotel room, where they bound and gagged her with handcuffs and tape before making away with more than $10 million worth of jewellery.
Kim later admitted the "horrific" ordeal allowed her to reflect on her "self-worth" and how she shouldn't be defined by how much money she has to her name.
She said: "My life has definitely changed a lot in the last two years.
"For a good year, I almost lost myself. I was never depressed, but I wasn't motivated to get up and work like I used to. It shook me.
"There was a lot of me that measured who I was by how much I had. I thought, 'Oh, I'm worth so much.' That needed to change in me.
"I'm grateful for the experience. Even though it was horrific and I wouldn't wish it upon anyone, it really did deeply change me to where now I feel like I can get back to myself.
"I felt like I was living in a bubble, and that opened me up to so much."
