Each square represents one ballot question. Hover to see details.
| Year | Question | Cost | Yes % | Result |
|---|---|---|---|---|
| 2007 | Hamilton Farm acquisition | $13.6M | 78.8% | Passed |
| 2023 | Lynch Elementary construction | — | 82.4% | Passed |
| 2013 | Winchester High School renovation | — | 68.0% | Passed |
| 2002 | Operating & capital stabilization override | $4.55M | 56.8% | Passed |
| 1998 | McCall Middle School renovation | $17.7M | 51.4% | Passed |
| 2001 | Ambrose Elementary construction | $15M | 48.3% | Failed |
| 2004 | Operating override (December) | $3.93M | 43.6% | Failed |
| 1991 | Health Dept. & services overrides (5 questions) | avg. $185K | avg. 40% | Failed |
1991 was the low point. All five questions on the March 1991 ballot failed, with voter support averaging just 40 percent across the five overrides. The highest-performing question — a $27,000 Library Book Account — still fell short with 45 percent. No other single election in the dataset saw every question rejected.
Operating overrides almost always failed — until recently. From 1991 through 2013, only two of 14 general operating overrides passed at the polls, a 14 percent success rate. Since 2019, voters have approved every Prop 2½ override put before them, a five-for-five streak that signals a meaningful shift in how Winchester voters view tax increases for services.
The Hamilton Farm vote produced the widest margin of victory. The 2007 debt exclusion for the $13.6 million Hamilton Farm acquisition earned 78.8 percent support and a margin of 3,774 votes — the largest raw margin of any question in these records — drawing nearly 6,600 voters to a special election in March. Among low-turnout elections, the 2022 Northeast Vocational High School question (91.9 percent) and the 2023 Lynch Elementary School question (82.4 percent) achieved higher approval rates on smaller electorates.
School projects now pass reliably. After the 1996 school construction question failed and the 2001 Ambrose Elementary vote fell just 134 votes short, Winchester has approved seven of eight school-related ballot questions since 1998. The 2023 Lynch Elementary School construction earned 82.4 percent support, the highest approval rate of any school question in the dataset.