10 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Winchester | 1 | 27,749 | 28,115 | -0.18% | 3,018 | 9 | City |
| Winchester | 2 | 27,749 | 28,003 | -0.18% | 3,018 | 9 | City |
| Shawneeland | 3 | 2,466 | 2,142 | 1.65% | 325 | 8 | CDP |
| Lake Holiday | 4 | 2,315 | 2,622 | 1.18% | 682 | 3 | CDP |
| Stephens City | 5 | 2,192 | 2,021 | 1.48% | 904 | 2 | Town |
| Stephens City | 6 | 2,192 | 2,031 | 1.48% | 904 | 2 | Town |
| Middletown | 7 | 1,465 | 1,353 | 1.45% | 1,890 | 1 | Town |
| Middletown | 8 | 1,465 | 1,358 | 1.45% | 1,890 | 1 | Town |
| Brucetown | 9 | 294 | 213 | 7.3% | 519 | 1 | CDP |
| Gore | 10 | 45 | 113 | 7.14% | 51 | 1 | CDP |
Winchester is the largest city in Frederick County, with a population of 27,749.
Gore is the smallest city in Frederick County, with a population of 45.
There are 10 cities in Frederick County, Virginia.