Each edition grades its towns against each other only.
Windsor gives you more for your money than most places: homes are within reach, about $350K for a typical one, or 4.3 years of the Virginia Beach metro’s $82K median household income. It grades B+ overall, ranked 122nd of 249 in Virginia. On the plus side, its schools outperform 80% of the state's. 17% of adults 25 and older hold a bachelor’s degree or more in Windsor, below both the Virginia town median (44%) and the median of U.S. towns (29%). Windsor has 2 places on the National Register of Historic Places, among them Boykin's Tavern and Henry Saunders House.
Where Windsor beats most towns.
| School | Grades | Students |
|---|---|---|
| Georgie D. Tyler Middle | 6–8 | 368 |
| Windsor High | 9–12 | 508 |
William Scott FarmsteadWhere Windsor’s working residents go each day. Line width shows the share.
Census LEHD 2023
Each subject compared with towns across the country (schools within Virginia), ordered by how far Windsor is from typical.
How TownRatings grades towns →
Census counts: 266 in 1880, 2,746 in 2020. The archive holds 18 old photos and papers going back to 2005 and 4 maps from 1919 on.
2 places on the National Register of Historic Places.
Who provides power, water and the rest in Windsor, and how to reach them.
EPA SDWIS (Oct 9, 2026) · HIFLD + EIA-861 2025 · Census 2020 ZCTAs · NCES 2024–25 · registration: vote.gov, updated Sep 30, 2026.
Ordered by what stands out in Windsor.
Windsor pairs an A− for schools with modest home prices, trades lower home prices for longer drives to work and fares better on crime within Virginia than nationally.
1,643 jobs are based in Windsor, 1.6 for every working resident, so most of the people who work here commute in.
Most working residents leave Windsor for work: only 7% work in town. Windsor’s average trip to work is 32 minutes. Since 2013, Windsor has added 358 jobs, to 1,643 in 2023.
| Windsor | Virginia towns | U.S. towns | |
|---|---|---|---|
| Average trip to work | 32 minutes | 27 minutes | 25 minutes |
| Median household income | $69,000 | $102,000 | $80,000 |
| Below the poverty line | 12% | 7.7% | 9.6% |
Census LEHD 2023 · ACS
Its A− for schools comes with a B+ for cost of living: the typical home is worth about $350K.
Its public schools are run by the Isle of Wight County Public Schools. Its two schools are below. The largest public high school is Windsor High, with 508 students.
| School | Level | Students | Letter |
|---|---|---|---|
| Georgie D. Tyler MiddleLargest public middle schoolGrades 6–8 | Grades 6–8 | 368 | B− |
| Windsor HighLargest public high schoolGrades 9–12 | Grades 9–12 | 508 | B+ |
NCES · EDFacts · graded within VA on state tests and graduation
Expected storm and flood damage is lower than in 74% of U.S. communities.
FEMA National Risk Index · OpenFEMA
Windsor has mild winters and warm summers, with plenty of rain. The July high in Windsor is 89°F.
NOAA U.S. Climate Normals, 1991–2020
Homes are within reach (about $350K for the typical one, B+ for cost of living), but half of working residents commute more than 23 miles.
81% of Windsor households own their home. The typical Windsor home is worth about $350,000, up 4% in a year, 15% below the Virginia typical home.
| Windsor | Virginia towns | U.S. towns | |
|---|---|---|---|
| Median rent | $950 a month | $1,764 a month | $1,185 a month |
| Households that own their home | 81% | 68% | 73% |
Census ACS, 2020–24 · Zillow Home Value Index · Redfin Data Center
At 15.1 crimes per 1,000 residents a year, it reports less crime than 84% of Virginia’s graded towns.
FBI crime data, 2025 · crimes reported to police
| Windsor | Virginia towns | U.S. towns | |
|---|---|---|---|
| Miles of trail per square mile | 0.2 miles per square mile | 0.7 | 0.4 |
| Conserved land | 5.1% | 4.6% | 4.3% |
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Robinson Park | — | 1 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
Windsor beats the Virginia average on 0 of 32 CDC measures and trails it on 5. 40% of adults have high blood pressure in Windsor.
| Windsor | Virginia towns | U.S. towns | |
|---|---|---|---|
| High blood pressure (CDC PLACES) | 40% | 33% | 35% |
| Diabetes (CDC PLACES) | 14% | 11% | 12% |
| Binge drink (CDC PLACES) | 14% | 14% | 16% |
| Yearly checkup (CDC PLACES) | 81% | 79% | 79% |
| What stands out | Windsor | VA |
|---|---|---|
| More adults with arthritis | 31.4% | 26.2% |
| More adults with COPD | 7.4% | 6.2% |
| More adults who have had a stroke | 3.9% | 3.3% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
1 within 15 miles of the center of Windsor
About 5 of every 100 Windsor residents are enrolled in college, against 7 across Virginia.
2 places in Windsor on the National Register of Historic Places.
3 notable people were born in Windsor.
Town in Virginia, United States
Windsor is an incorporated town in Isle of Wight County in the Hampton Roads region of southeastern Virginia, United States. It is located near the crossroads of U.S. routes 460 and 258. As of the 2020 census, Windsor had a population of 2,746.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
Short answers, built from the data on this page.
By most measures, yes. Windsor grades B+ overall, better than 72% of U.S. towns and #122 of 249 in Virginia. It grades B− for health, B for safety and A− for schools.
Not for the area. Cost of living, which also weighs rents, property taxes and how many households pay 30% or more of their income for housing, grades B+.
3 notable people were born here, including Daniel Brown and Richard J. Holland.
