| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Winchester | 1 | 28,291 | 28,003 | 0.07% | 3,077 | 9 | City |
| Stephens City | 2 | 2,241 | 2,033 | 1.54% | 924 | 2 | Town |
| Middletown | 3 | 1,492 | 1,359 | 1.43% | 1,870 | 1 | Town |
Winchester is the largest city in Frederick County, with a population of 28,291.
Middletown is the smallest city in Frederick County, with a population of 1,492.
There are 3 cities in Frederick County, Virginia.