4 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Winona | 1 | 3,767 | 4,462 | -3.56% | 279 | 14 | City |
| Duck Hill | 2 | 1,471 | 656 | 12.46% | 1,423 | 1 | Town |
| Kilmichael | 3 | 545 | 634 | -3.2% | 185 | 3 | Town |
| Stewart | 4 | 159 | 50 | 7.43% | 141 | 1 | CDP |
Winona is the largest city in Montgomery County, with a population of 3,767.
Stewart is the smallest city in Montgomery County, with a population of 159.
There are 4 cities in Montgomery County, Mississippi.