"This is a historic investment in the future of our city and it's showing our belief in students and teachers that they deserve the very best," Mayor Caroline Simmons said.
On the lower end, some buildings will receive upgrades like solar panels, bathroom renovations and roof replacements.
On the higher end, work is currently being done to drill geothermal wells for what will be a brand new, bigger Roxbury Elementary School, holding grades kindergarten - eight, as opposed to the current building, which only holds K-5.
Across the street, work is also underway to build a brand new Westhill High School.
The new Roxbury School is scheduled to open for the 2028-29 school year, with Westhill to follow the year after.
Sixty to 80% of the costs at each site are being covered by the state.
"It's really unprecedented," said Matthew Quinones, the director of operations for the City of Stamford. "This is all about modernizing our school district, finding the most efficient ways to plan for capital investment, so it's about being proactive, not reactive."
The tough part for the moment is that a lot of the work is being done right next to buildings where class is currently in session, backing up traffic, taking up parking, and creating noise.
"We're always trying to make sure we're not interrupting the school day," said Scott Torre, a project manager at O&G Industries, which is doing the work at Roxbury. "We work with the principal to try to stay out of their way."
While the construction is going on however, the city is partnering with the construction companies to get the students involved so they can learn about the work and different types of sustainable technology being used.
"We kind of left vacant areas of the scrim open so they actually see," said Torre. "I loved that kind of stuff when I was a kid, it's why I got into the business so, I know there's a kid who's out there feeling just like I did."
Plans also call for building a brand new two-building elementary and middle school campus for students south of Interstate 95, with construction slated to start in 2027.