Winchester, MA: town finances
Strong savings (14% of budget vs 7.3% typical); 2 override votes since 2016; another override vote likely.
Budget grade
Better than 89% of MA towns · score 93 of 100
± Borderline: the score is within 2 points of the A/B cutoff, so a small change in the data could move the budget grade.
Ability to pay
Top 5% for income and property value
Shown separately; not part of the budget grade. Income per resident $109,898 (Census ACS 2020-24); property value (EQV) per resident $509,454 (DLS 2024).
Chance of an override vote
7 points on our 0-8 scale: Low 0-2, Medium 3-4, High 5+. It ranks towns; it is not a percentage.
The story in charts
Winchester: a $10M override rebuilt reserves, but the room it bought is gone
Winchester also appears in: The wealthiest big suburbs: fewer students, costlier schools, tax bills ahead of inflation
Key numbers
| Measure | Winchester | Median MA town |
|---|---|---|
| Typical tax bill, FY2026 (average single-family) | $18,272 | $6,755 |
| Tax bill as a share of median household income | 7.9% | 6.4% |
| Tax bill growth per year, FY2016-26 | 5.26% | 3.95% |
| Override vote dates, last 5 years | Yes (1 vote) | 35% of towns had one |
| Savings (reserves), % of budget, FY2024-26 average | 14.2% | 7.3% |
| Debt, % of property value, FY2023-25 (voter-approved debt at half weight) | 1.08% | 0.70% |
| Debt payments inside the tax cap, % of budget | 2.1% | 1.3% |
| Unused room under the tax cap, FY2026 (% of max levy) | 0.04% | 0.34% |
| School enrollment, 5-year change | -3% | -2% |
| Students per teacher, 2025-26 | 12.0 | 11.4 |
| Median single-family sale price, 2024 | $1.8M (148 sales) | $614k |
| Single-family price change, 2019-24 | +46.0% | +52.8% |
| Median household income (Census, 2020-24) | $230,198 | $113,750 |
| Population (DLS) | 22,640 | 10,585 |
Main school district: Winchester. Shaded = worse than the median town on tax bill share or enrollment. Medians are across all 351 towns with data.
Why this budget grade
Budget grade A, excellent (93/100, near the A/B line; better than 89% of MA towns): reserves averaged 14% of budget over FY2024-26 (state median 7.3%); debt 1.08% of property value with voter-approved debt at half weight (1.74% before; median 0.70%); debt payments inside the tax cap 2.1% of budget (median 1.3%). 76% of debt payments are voter-approved and paid outside the cap.
Why this chance of an override vote
Chance of an override vote: High (7 pts): almost no unused room under the tax cap (0.04% of max levy, +3); override votes since July 2016, latest 2023-01 (+2); voter-approved debt or capital increase passed since July 2021 (+1); school spending grew 4.5%/yr vs 3.7%/yr for the tax cap limit, FY2020-2025 (+1).
Context, not scored
Teacher jobs +4.1% last year; enrollment -3% over 5 yrs; tax bill 7.9% of median income (state median 6.4%).
"pts" are points toward the chance of an override vote. Max levy is the most the town can raise without a vote under Prop 2½. See how the budget grade works.
Override votes since July 2016
| Vote date | Result | Amount | Purpose (as listed by DLS) |
|---|---|---|---|
| Jan 7, 2023 | Passed | $400,000 | Capital Stabilization Fund |
| Mar 26, 2019 | Passed | $10,000,000 | Operating Budget And Building Stab Fund |
Source: MA DLS Proposition 2½ override vote file, as of 25 Oct 2026. One ballot can carry several questions.
See this town in the full data table →
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