Simon's Coffee Shop, a fixture between the Porter Square Red Line stop and Lesley University's campus, closed its doors on Monday after 23 years serving lattes and seasonal drinks to neighborhood regulars and college students. The closure at 1736 Massachusetts Ave. clears the way for demolition of the single-story building that has housed the cafe, with owner Simon Yu now hoping to relocate just across the street.
According to MassLive, Simon's Coffee Shop announced the closure in an Instagram post, and Yu said he expects to continue running a coffee shop across the street at 1741 Massachusetts Ave. He has not yet finalized or signed the agreement for that new location, the outlet reported, and he was unable to offer a reopening date. Yu told the publication he is very happy the shop can continue its legacy and offer the same products and services once it lands somewhere new.
A Farewell Before the Wrecking Ball
The night before closing, Yu hosted an evening farewell gathering where regulars were invited to write messages on the cafe's walls, take home non-movable decorations, and pick up coupons redeemable at whatever interim location eventually opens, according to Cambridge Day. Announcements posted on the shop's door and on social media had detailed the evening's schedule ahead of time. Yu originally established Simon's Coffee Shop in 2002 after purchasing and renaming an existing coffee house, building what became a 23-year footprint in the Porter Square area, per the same outlet's earlier reporting.
Demolition of the building at 1740 Massachusetts Ave. is scheduled to begin in early September, following utility shutoffs that included a gas disconnection late last month, kicking off an estimated 18- to 20-month construction timeline. The site will make way for Old North Development's six-story mixed-use project, a 64,330-square-foot building that will add 71 residential apartments, including 13 deed-restricted affordable units with two three-bedroom apartments, the outlet's reporting on the Cambridge Planning Board's review found.
Zero Parking, Dozens of Bike Spaces
The residential project will include zero on-site vehicle parking spaces, instead building out 75 long-term and 13 short-term bicycle parking spots — a design that reflects Cambridge policies encouraging car-free construction near transit hubs, according to the Neighborhood Nine Coalition. The project was able to move forward largely by-right thanks to multi-family zoning reforms the Cambridge City Council enacted in February 2025, which permit residential buildings up to six stories along major transit corridors when developers meet inclusionary housing thresholds. That citywide overhaul was designed to spur housing production amid a regional housing shortage, the coalition notes.
Architectural plans from Peter Quinn Architects call for five retail and commercial spaces spread across the ground floor and basement of the new building, with a designated return space for Simon's Coffee Shop facing Linnaean Street, Cambridge Day reported in November. The primary residential lobby, by contrast, will face Massachusetts Avenue. Lead developer Adam Siegel has said Old North Development plans to cover the full cost of building out a new storefront for the cafe and to offer Yu a below-market lease rate to support its eventual return.
Neighbors Displaced, One Finds a New Home
Simon's wasn't the only longtime tenant forced out. Keezer's Classic Clothing, a 131-year-old menswear shop founded in 1895, relocated in late August to 1730 Massachusetts Ave. under a five-year lease, having operated out of the basement space at 1740 Massachusetts Ave. for nine years. The shop had previously been displaced from Cambridgeport back in 2017. A third commercial occupant of the property, a Walgreens pharmacy, permanently closed on July 9 ahead of the planned teardown, with customer prescriptions automatically transferred to neighboring chain locations.
Whether Yu will finalize the lease across the street, and how the cafe will bridge an 18- to 20-month construction hiatus without a storefront, remain open questions. Independent retailers navigating multi-year redevelopment timelines don't always make it back to reopen in the buildings that replace them, a tension that has shadowed this stretch of Massachusetts Avenue since the project was first announced. For now, Simon's regulars are left with coupons for a location that doesn't exist yet, and the promise of a return once the dust settles.
