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The Winchester Select Board recently voted unanimously to accept a comprehensive State of the Town report and schedule a Special Town Meeting for Feb. 9 to present the findings to residents and Town Meeting members.
The report, which concluded a months-long analysis by representatives from the Select Board, School Committee, Finance Committee, Capital Planning Committee and Planning Board, presents Winchester as “operating from a position of strength” while facing “significant and immediate risks” requiring new resources to stabilize the town’s fiscal picture.
The board accepted the report in draft form at its Jan. 12 meeting, but did not formally adopt a specific override figure. Operating models presented to the board show scenarios ranging from $10 million to $13 million over three or four years.
Structural deficit driven by rising costs
The town faces a structural deficit exceeding $4 million in fiscal year 2027, driven by escalating costs against revenue constrained by Proposition 2 1/2.
Health insurance premiums rose 18.92% in fiscal year 2026, growing from $13.9 million to approximately $16.5 million, an increase of roughly $2.6 million on Winchester’s approximately $161 million total operating budget.
The property tax levy can grow at a maximum of 2.5% per year under state law, meaning the levy on Winchester’s current tax base can increase by roughly $3.3 million annually before requiring an override.
Select Board member Paras Bhayani, who chaired the State of the Town committee, said Town Meeting members need to understand the implications for Spring Town Meeting regardless of whether an override succeeds.
“Town Meeting also needs to be aware of what are the implications for Spring Town Meeting,” Bhayani said. “I mean, I think that’s the biggest hook for why to do it as a special town meeting to me.”
The School Committee prioritized $4.5 million in program additions over four years, with $2.3 million phased in during fiscal year 2027, for needs including literacy and math curriculum, academic supports, high school course expansions and student mental health services.
The School Committee’s fiscal year 2026 budget totaled $70.9 million, representing a 7.15% increase described as maintaining level services without funding new initiatives.
The Select Board approved $800,000 of $1.6 million in municipal department requests for priorities including the Council on Aging, recreation programs, conservation and tree programs, community health and technology resilience.
Capital backlog totals $54 million
Capital needs total approximately $85.6 million over five years, with $31.7 million available from stabilization funds, leaving a $53.9 million shortfall. Top priorities include Town Hall restoration at $19.4 million and critical systems at McCall, Lincoln and Ambrose schools totaling $17.2 million.
Roger McPeek, chair of the Capital Planning Committee, said presenting capital and operating needs together helped the community understand the full scope.
“I think that being able to present, at one time all of the numbers that we see going forward, and being able to advertise, if you will, to the rest of the community that more often than not, is looking at the operational side of some of the capital problems are, and the magnitude of them that we’re facing was, was really good,” McPeek said.
Karen Maruyama Bolognese, chair of the School Committee, said the process provided an opportunity to share school data and challenges with the broader community.
“Because schools are are a big beast of a project, it’s been a great opportunity to introduce some of the data from the schools, School Department, some of the challenges, some of the ways that, and some of the prioritization of those challenges and all of the planning over the next five years,” Bolognese said.
Operating models show that without new revenue, town reserves would decline significantly. Reserves are projected to range from 4.1% to 14% of the operating budget depending on the override amount and strategic additions the town implements. At the low end, 4.1% of a $161 million budget equals approximately $6.6 million in reserves; at 14%, reserves would total roughly $22.5 million.
Bhayani told the board that increasing commercial rates at the transfer station by 50% would generate $500,000 annually, while changes to retiree health insurance cost sharing could generate $1.4 million per year. However, he cautioned against relying on revenue projections facing political challenges.
“I do think there’s real risk when I look at a page six of all these initiatives coming to fruition,” Bhayani said. “I layered them all on as an illustration, but they certainly would not be in my base case.”
Tax impact on median household
Select Board Chair Michelle Prior emphasized presenting residents with complete tax impact information, including the potential override plus debt service from Lynch School, Morocco Culvert and South Reservoir Dam projects, as well as Community Preservation Act assessment growth.
“I think for the voters to understand that in addition to whatever the Select Board decides and the referendum, whatever the voters decide, there is debt service coming on, probably the $600 to $700 per year per household for projects,” Prior said.
Select Board member Bill McGonigle expressed concern about the reserve projections and the assumptions underlying the revenue scenarios.
“I just continue to be a little nervous putting too much emphasis on what we might get for revenue, and we need to continue to chase after it, but we can’t rely on it,” McGonigle said. “I don’t like seeing the reserves get as low as I see them getting in some of these boxes.”
The median Winchester home valued at $1.6 million would see approximately $1,300 in additional annual taxes from a $10 million override, based on assessor figures showing $128 to $138 per $1 million in assessed value. An $11 million override would add another $130 to that figure, bringing the total increase to approximately $1,430 annually for the median household.
Select Board member Michael Bettencourt said continuing the State of the Town committee would help ensure accountability in implementing approved spending.
“Once we have an override, which I think will be successful, I hope it will be successful to say the most important thing is that here we’re doing the things that we said that we’re going to do, right?” Bettencourt said.
The Special Town Meeting will include one article “to hear an act upon the reports of town official sports committees and commissions regarding the State of the Town of the budget outlook.”
The board plans information sessions Jan. 27 and Feb. 4 for Town Meeting members, with public forums scheduled for Feb. 2 and potentially Feb. 10. The board will meet Jan. 26 to finalize presentation details and select a tentative override number.
Will Dowd is a Massachusetts journalist who covers municipal government and community life for Winchester News. He previously co-founded the Marblehead Current and now runs The Marblehead Independent, a reader-funded digital newsroom.
