“They have expressed their desire to be great community partners and thus far have proven themselves to be just that,” Jillson said.

OUT WITH THE OLD

Despite the exciting changes brought about by the transitions in ownership, many of Chan’s purchases have been followed by the departure of longtime tenants.

“The market is what the market is,” Jillson said. “Any purchaser and any developer can pay whatever they deem appropriate.”

Iconic Cambridge bar and restaurant UpStairs on the Square was the first establishment to shut down after Chan’s acquisitions of property. After 31 years of business, the restaurant announced its closing soon after Chan purchased the property at Winthrop Square, and restaurant owners decided not to renew their lease.

While former co-owner of UpStairs on the Square Mary-Catherine Deibel said Chan’s purchase of the property presented a logical time for her to close her establishment. She said she is excited to see what the future of the space holds.

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According to Boston Restaurant Talk, a new farm-to-table eatery called Parsnip is slated to open in UpStairs on the Square’s place.

“I think it’s great that the building is staying an indepently owned restaurant,” Deibel said. “It will bring vitality to the Square and, based on what I see so far, the restaurant will be high quality and interesting.”

Similarly, after nine years in the square, Indian bistro Tamarind Bay was forced to close its doors when the restaurant’s rent doubled following Chan’s purchase of the property at 75 Winthrop St.

The space will be occupied by Night Market, a Japanese restaurant operated by Gerald Chan’s son Ash Chan, an entrepreneur who previously owned and operated the liquid nitrogen ice cream shop Churn2.

SOME THINGS NEVER CHANGE

In spite of all the closures, Chan said he is working to preserve the culture of Harvard Square.

Not all of Chan’s properties are transferring tenants. Grendel’s Den, the bar and restaurant located at 81 Winthrop St., has no plans to change occupancy. According to Kari Kuelzer, co-owner and general manager, their lease does not end until 2020.

“We didn’t renegotiate the lease. We’ve had the lease since 1999 when we had a lease with Gregory Carr,” Kuelzer said, referring to entrepreneur and philanthropist Gregory C. Carr, an alumnus of the Harvard Kennedy School.