Each edition grades its towns against each other only.
Yes, by almost any measure. Winchester earns an A+, 13th among Massachusetts's 282 graded towns. On CDC health estimates it is near the top nationally, the median household earns $230K, and it reports less crime per resident than 92% of U.S. towns. The exception is cost of living: the typical home is worth about $1.5 million, 13.2 years of the Boston metro’s $116K median household income. History is its standout character grade: an A+, better than 99% of U.S. towns, with 67 places on the National Register. 79% of adults 25 and older hold a bachelor’s degree or more in Winchester, above both the Massachusetts town median (47%) and the median of U.S. towns (29%). Winchester is more walkable than 97% of U.S. towns. Its National Register listings include Sanborn House and Edward A. Brackett House.
Where Winchester beats most towns.
Capt. Josiah Locke House| Widest gap | Winchester | MA |
|---|---|---|
| Fewer older adults who have lost all their teeth | 5.3% | 11.9% |
Census counts: 1,353 in 1850, 22,970 in 2020. The archive holds 6 old photos and papers going back to 1805 and 6 maps from 1893 on.
67 places on the National Register of Historic Places.
Each subject compared with towns across the country (schools within Massachusetts), ordered by how far Winchester is from typical.
How TownRatings grades towns →
Museums, parks, gardens and other places to visit around Winchester. Close and well known come first.
Big draw8 mi Stadium & arenaFenway Park
Big draw26 mi Stadium & arenaGillette Stadium
Big draw8 mi MuseumIsabella Stewart Gardner Museum
10 mi LakeWalden Pond
8 mi AttractionFreedom Trail
6 mi Stadium & arenaHarvard StadiumFenway Park: Gatorfan252525, CC BY-SA 4.0 · Gillette Stadium: Bernard Gagnon, CC BY-SA 3.0 · Isabella Stewart Gardner Museum: Sean Dungan, CC BY-SA 4.0 · Walden Pond: Victorgrigas, CC BY-SA 3.0 · Freedom Trail: Ingfbruno, CC BY-SA 3.0 · Harvard Stadium: Nick Allen, CC BY-SA 4.0
Who provides power, water and the rest in Winchester, and how to reach them.
EPA SDWIS (Oct 9, 2026) · HIFLD + EIA-861 2025 · Census 2020 ZCTAs · NCES 2024–25 · registration: vote.gov, updated Nov 18, 2024.
Ordered by what stands out in Winchester.
Winchester reports less crime than Lexington or any other graded neighbor and has less tooth loss than most of Massachusetts, but it has homes that cost more against local pay than most of Massachusetts.
At 13.2 years of the Boston metro’s $116K median household income, the typical home (about $1.53M) costs more against local pay than in 97% of Massachusetts towns; that ratio is one input to its D for cost of living.
Winchester’s median rent is $2,279 a month. The typical Winchester home is worth about $1,530,000, up 2.6% in a year, more than twice the Massachusetts typical home.
| Winchester | Massachusetts towns | U.S. towns | |
|---|---|---|---|
| Median rent | $2,279 a month | $1,682 a month | $1,185 a month |
| Households that own their home | 82% | 79% | 73% |
Census ACS, 2020–24 · Zillow Home Value Index · Redfin Data Center
Its A for schools comes with a D for cost of living: the typical home is worth about $1.53M.
Its public schools are run by the Winchester school district. Three of its 11 schools are below, each with why it’s listed.
| School | Level | Students | Letter |
|---|---|---|---|
| McCall MiddleLargest public middle schoolGrades 6–8 | Grades 6–8 | 1,036 | A− |
| Winchester High SchoolLargest public high schoolGrades 9–12 | Grades 9–12 | 1,404 | A+ |
| Vinson-Owen ElementaryTop results in townGrades PK–5 | Grades PK–5 | 441 | A+ |
NCES · EDFacts · graded within MA on state tests and graduation
21 miles of trail in 30 parks and preserves. The trail density in Winchester is 3.3 miles per square mile. The biggest place to walk is Middlesex Fells Reservation, 304 acres with 9 miles of trail.
| Winchester | Massachusetts towns | U.S. towns | |
|---|---|---|---|
| Miles of trail per square mile | 3.3 miles per square mile | 1.8 | 0.4 |
| Conserved land | 19% | 19% | 4.3% |
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Middlesex Fells Reservation | 9 mi | 304 |
| 2. Brooks Parkhurst Town Forest | 1.5 mi | 28 |
| 3. Sucker Brook Conservation Area | 0.6 mi | 13 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
Its widest gap with Massachusetts is tooth loss: 5.3% of those 65+ have lost all their teeth, against 11.9% statewide. Against the 593 U.S. towns with household incomes like Winchester’s, it is healthier than 83%, a smaller edge than it has nationally: part of it comes with its incomes.
Winchester beats the Massachusetts average on 22 of 32 CDC measures and trails it on 1. 12% of adults report frequent mental distress in Winchester.
| Winchester | Massachusetts towns | U.S. towns | |
|---|---|---|---|
| Obesity (CDC PLACES) | 22% | 28% | 35% |
| Frequent mental distress (CDC PLACES) | 12% | 16% | 17% |
| Frequent physical distress (CDC PLACES) | 9.1% | 12% | 14% |
| Smoke cigarettes (CDC PLACES) | 7% | 11% | 14% |
| What stands out | Winchester | MA |
|---|---|---|
| Fewer older adults who have lost all their teeth | 5.3% | 11.9% |
| Fewer uninsured adults | 2.4% | 5.2% |
| More adults who have had cancer | 9.9% | 8.5% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
Its A tops all 5 graded towns on its borders; Lexington (A) comes closest. Violent crime is rare: 5 reported in 2025, 0.2 per 1,000 residents.
Among 277 Massachusetts towns, just 9 have a lower violent crime rate than Winchester.
| Winchester | Massachusetts towns | U.S. towns | |
|---|---|---|---|
| Violent crimes per 1,000 (2025) | 0.2 per 1,000 residents | 1.5 | 1.6 |
| Property crimes per 1,000 (2025) | 4.1 per 1,000 residents | 4.9 | 9.9 |
FBI crime data, 2025 · crimes reported to police
Jobs based here fell from 8,057 in 2013 to 6,295. 33.8% of workers work from home, against 18.6% across Massachusetts.
Only 8 of the 283 Massachusetts towns we compare have a higher median household income than Winchester. 4.7% of Winchester residents live below the poverty line. Since 2013, Winchester has lost 1,762 jobs, to 6,295 in 2023.
| Winchester | Massachusetts towns | U.S. towns | |
|---|---|---|---|
| Work from home | 34% | 18% | 11% |
| Median household income | $230,000 | $120,000 | $80,000 |
| Average trip to work | 31 minutes | 30 minutes | 25 minutes |
| Below the poverty line | 4.7% | 6% | 9.6% |
Census LEHD 2023 · ACS
Winchester has chilly, snowy winters and pleasant summers. July afternoons reach 83°, January nights drop to 19° and about 64 inches of snow falls in a winter.
NOAA U.S. Climate Normals, 1991–2020
145 flood insurance claims have been filed here, and 29 properties have flooded more than once.
Expected storm and flood damage is lower than in 57% of U.S. communities. Since 1979, 145 flood insurance claims have been paid out in Winchester.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
53 within 15 miles of the center of Winchester
About 5 of every 100 Winchester residents are enrolled in college, against 8 across Massachusetts.
Where Winchester’s working residents go each day. Line width shows the share.
Census LEHD 2023
67 places in Winchester on the National Register of Historic Places.
31 notable people were born in Winchester.
Town in Massachusetts, United States
Winchester is a town in Middlesex County, Massachusetts, United States, located 8.2 miles (13.2 km) north of downtown Boston as part of the Greater Boston metropolitan area. It is also one of the wealthiest municipalities in Massachusetts. The population was 22,970 at the 2020 United States Census.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
5 towns share a border with Winchester.
Short answers, built from the data on this page.
Yes, by almost any measure. Winchester grades A+ overall, among the top 2% of U.S. towns and #13 of 282 in Massachusetts. It grades A+ for health, A for safety and A for schools. Cost of living is its weak spot, with a D.
Yes. Cost of living, which also weighs rents, property taxes and how many households pay 30% or more of their income for housing, grades D.
31 notable people were born here, including Mark A. Milley and Brad Whitford.
