12 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Haleyville | 1 | 4,305 | 4,355 | -0.19% | 514 | 8 | City |
| Haleyville | 2 | 4,305 | 4,342 | -0.19% | 514 | 8 | City |
| Double Springs | 3 | 1,123 | 1,115 | 0.18% | 219 | 5 | Town |
| Double Springs | 4 | 1,123 | 1,112 | 0.18% | 219 | 5 | Town |
| Addison | 5 | 680 | 661 | 0.59% | 181 | 4 | Town |
| Addison | 6 | 680 | 659 | 0.59% | 181 | 4 | Town |
| Lynn | 7 | 632 | 610 | 0.64% | 59 | 11 | Town |
| Lynn | 8 | 632 | 610 | 0.64% | 59 | 11 | Town |
| Arley | 9 | 334 | 327 | 0.3% | 86 | 4 | Town |
| Arley | 10 | 334 | 326 | 0.3% | 86 | 4 | Town |
| Natural Bridge | 11 | 41 | 40 | 0% | 94 | 0 | Town |
| Natural Bridge | 12 | 41 | 40 | 0% | 94 | 0 | Town |
Haleyville is the largest city in Winston County, with a population of 4,305.
Natural Bridge is the smallest city in Winston County, with a population of 41.
There are 12 cities in Winston County, Alabama.