7 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Plentywood | 1 | 1,615 | 1,668 | -0.68% | 1,190 | 1 | City |
| Medicine Lake | 2 | 238 | 245 | -0.83% | 603 | 0 | Town |
| Westby | 3 | 160 | 167 | -1.23% | 285 | 1 | Town |
| Outlook | 4 | 79 | 82 | -1.25% | 63 | 1 | Town |
| Reserve | 5 | 34 | 36 | 6.25% | 25 | 1 | CDP |
| Redstone | 6 | 24 | 31 | 9.09% | 71 | 0 | CDP |
| Homestead | 7 | 19 | 10 | 5.56% | 44 | 0 | CDP |
Plentywood is the largest city in Sheridan County, with a population of 1,615.
Homestead is the smallest city in Sheridan County, with a population of 19.
There are 7 cities in Sheridan County, Montana.