Each edition grades its towns against each other only.
Winchester gives you more for your money than most places: a typical home costs about $251K, 3.5 years of the Lexington metro’s $72K median household income. It grades C overall, 98th of 138 graded towns in Kentucky. The low prices come with trade-offs. Residents are less healthy than 83% of U.S. towns on CDC estimates, and it reports more crime per resident than 79% of U.S. towns, including 34 violent crimes reported to the FBI in 2025. Its National Register listings include Fort Boonesborough Townsite Historic District and Providence Baptist Church. Winchester’s property crime rate is 22.4 per 1,000 residents, above both Kentucky’s towns (8.2) and U.S. towns (9.9). The biggest park or preserve is Winchester Traveling Trail, at 23 acres.
Where Winchester beats most towns.
Census counts: 130 in 1800, 19,134 in 2020. The archive holds 12 old photos and papers going back to 1877 and 4 maps from 1952 on.
16 places on the National Register of Historic Places.
Each subject compared with towns across the country (schools within Kentucky), ordered by how far Winchester is from typical.
How TownRatings grades towns →
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 is healthier than towns with similar incomes, has home values climbing faster than Kentucky’s and has milder winter nights than most of the country, though not than most of Kentucky.
Against the 7,230 U.S. towns with household incomes like Winchester’s, it is less healthy than 66%, so its C− isn’t only a matter of income.
20% of Winchester adults smoke cigarettes. Winchester beats the Kentucky average on 0 of 31 CDC measures and trails it on 4. 41% of Winchester adults sleep under 7 hours.
| Winchester | Kentucky towns | U.S. towns | |
|---|---|---|---|
| Smoke cigarettes (CDC PLACES) | 20% | 18% | 14% |
| Sleep under 7 hours (CDC PLACES) | 41% | 40% | 36% |
| Frequent physical distress (CDC PLACES) | 16% | 15% | 14% |
| Obesity (CDC PLACES) | 40% | 39% | 35% |
| What stands out | Winchester | KY |
|---|---|---|
| More uninsured adults | 7.6% | 5.4% |
| More adults facing housing insecurity | 13.4% | 11.7% |
| More adults facing food insecurity | 17.5% | 15.5% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
Its public schools are run by the Clark County school district. Two of its 13 schools are below, each with why it’s listed.
| School | Level | Students | Letter |
|---|---|---|---|
| Rev. Henry E. Baker Sr. Interm. SchoolLargest public middle schoolGrades 5–6 | Grades 5–6 | 767 | B+ |
| George Rogers Clark High SchoolLargest public high schoolGrades 9–12 | Grades 9–12 | 1,578 | B− |
NCES · EDFacts · graded within KY on state tests and graduation
Reported crimes fell from 628 to 470 over the last three FBI years, a drop beyond ordinary year-to-year swings.
Winchester reports more crime per resident than most U.S. towns we grade: about 79% report less.
FBI crime data, 2025 · crimes reported to police
Expected storm and flood damage is lower than in 72% of U.S. communities. Since 1978, 75 flood insurance claims have been paid out in Winchester.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
| Winchester | Kentucky towns | U.S. towns | |
|---|---|---|---|
| Conserved land | 2.7% | 1.7% | 4.3% |
| Miles of trail per square mile | 0.3 miles per square mile | 0.3 | 0.4 |
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Winchester Traveling Trail | 0.8 mi | 23 |
| 2. College Park | 0.2 mi | 9 |
| 3. Wiseman Park | — | 4 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
January nights average 24.5°: milder than most of the country, but colder than 75% of Kentucky places with climate records; July afternoons average 86.5°.
Winchester has chilly winters and warm summers, with plenty of rain. About 9 inches of snow falls in a winter.
| Winchester | Kentucky towns | U.S. towns | |
|---|---|---|---|
| July high | 87°F | 87°F | 85°F |
| January low | 25°F | 25°F | 22°F |
NOAA U.S. Climate Normals, 1991–2020
About one in 4 of Winchester’s working residents works in town. 17% of residents live below the poverty line in Winchester. Since 2013, Winchester has added 1,172 jobs, to 10,799 in 2023.
| Winchester | Kentucky towns | U.S. towns | |
|---|---|---|---|
| Working residents who work in town | 25% | 15% | 8% |
| Below the poverty line | 17% | 16% | 9.6% |
| Median household income | $54,000 | $60,000 | $80,000 |
| Work from home | 14% | 10% | 11% |
Census LEHD 2023 · ACS
Home values rose 40% in five years, to about $251K, against 25% across Kentucky.
Typical home values rose 4.7% in the year to September 2026.
| Winchester | Kentucky towns | U.S. towns | |
|---|---|---|---|
| Households that own their home | 61% | 59% | 73% |
| Median rent | $916 a month | $937 a month | $1,185 a month |
Zillow Home Value Index · Redfin Data Center
22% of adults 25 and older have a bachelor’s degree or more, vs 28% across Kentucky.
| Winchester | Kentucky towns | U.S. towns | |
|---|---|---|---|
| Under 18 | 21% | 22% | 22% |
| Bachelor’s degree or more, 25+ | 22% | 26% | 29% |
| Median age | 40.1 years | 37.6 years | 40.5 years |
52% women, 48% men
About 91 men for every 100 women (the survey’s margin: ±1.5 points). Across Kentucky, 50.5% of residents are women. Median age: women 41.4, men 37.5.
| Winchester | KY | U.S. | |
|---|---|---|---|
| Under 10 | 10.2% | 12.1% | 11.6% |
| 10 to 17 | 10.4% | 10.5% | 10.3% |
| 18 to 24 | 8.4% | 9.1% | 9.1% |
| 25 to 34 | 15.3% | 13.1% | 13.7% |
| 35 to 44 | 11.3% | 12.6% | 13.2% |
| 45 to 54 | 14.1% | 12.3% | 12.2% |
| 55 to 64 | 12.2% | 13% | 12.7% |
| 65 to 74 | 10.9% | 10.5% | 10.2% |
| 75 and older | 7.3% | 6.8% | 7% |
| No diploma | 11.3% | 11.1% | 10.4% |
| High school | 36.2% | 32.6% | 26% |
| Some college | 23% | 19.7% | 19.1% |
| Associate’s | 7% | 9% | 8.8% |
| Bachelor’s | 14.3% | 16.2% | 21.6% |
| Graduate | 8.1% | 11.3% | 14.1% |
U.S. Census Bureau · ACS 2020-2024 5-year estimates
Museums, parks, gardens and other places to visit around Winchester. Close and well known come first.
17 mi Stadium & arenaKroger Field
17 mi Stadium & arenaRupp Arena
34 mi Canyon & gorgeRed River Gorge
8 mi State parkFort Boonesborough State Park
18 mi GardenLexington Cemetery
21 mi Park & preserveKentucky Horse ParkKroger Field: Navin75, CC BY-SA 2.0 · Rupp Arena: The original uploader was Analogue Kid at English Wikipedia., CC BY 2.5 · Red River Gorge: Robert G. Davis, NWSRS, Public domain · Fort Boonesborough State Park: Bubba73, CC BY-SA 3.0 · Lexington Cemetery: Analogue Kid at en.wikipedia, CC BY 2.5 · Kentucky Horse Park: Wes Blevins, CC BY-SA 2.5
None within 15 miles of Winchester; the nearest are
About 4 of every 100 Winchester residents are enrolled in college, against 6 across Kentucky.
16 places in Winchester on the National Register of Historic Places.
18 notable people were born in Winchester.
City in Kentucky, United States
Winchester is a city in and the county seat of Clark County, Kentucky, United States. The population was 19,134 at the 2020 census. It is part of the Lexington-Fayette, KY Metropolitan Statistical Area. Winchester is located roughly halfway between Lexington and Mt. Sterling. Winchester is a home-rule class city under Kentucky law.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
Short answers, built from the data on this page.
Winchester grades C overall, better than 27% of U.S. towns and #98 of 138 in Kentucky. It grades C− for health, C− for safety and B for schools. Health is its weak spot, with a C−.
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+.
18 notable people were born here, including Helen Thomas and Allen Tate.
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