26 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Clinton | 1 | 9,509 | 9,209 | 0.63% | 1,043 | 9 | City |
| Clinton | 2 | 9,019 | 8,757 | 0.43% | 259 | 35 | Township |
| Windsor | 3 | 3,448 | 3,333 | 0.5% | 97 | 35 | Township |
| Windsor | 4 | 2,874 | 2,772 | 0.7% | 1,188 | 2 | City |
| Fields Creek | 5 | 1,773 | 1,723 | 0.45% | 57 | 31 | Township |
| Clinton | 6 | 1,593 | 1,507 | 0.44% | 24 | 65 | Township |
| Leesville | 7 | 1,072 | 1,032 | 0.66% | 26 | 42 | Township |
| Osage | 8 | 794 | 765 | 0.76% | 20 | 39 | Township |
| Tebo | 9 | 764 | 747 | 0.39% | 16 | 47 | Township |
| White Oak | 10 | 760 | 740 | 0.53% | 24 | 32 | Township |
| Bethlehem | 11 | 717 | 690 | 0.84% | 17 | 43 | Township |
| Deepwater | 12 | 600 | 585 | 0.5% | 17 | 36 | Township |
| Urich | 13 | 478 | 467 | 0.42% | 1,183 | 0 | City |
| Deer Creek | 14 | 456 | 444 | 0.44% | 14 | 33 | Township |
| Shawnee | 15 | 444 | 432 | 0.45% | 11 | 42 | Township |
| Calhoun | 16 | 407 | 396 | 0.49% | 414 | 1 | City |
| Montrose | 17 | 393 | 385 | 0.26% | 689 | 1 | City |
| Deepwater | 18 | 390 | 358 | 1.56% | 460 | 1 | City |
| Creighton | 19 | 333 | 327 | 0.3% | 965 | 0 | City |
| Big Creek | 20 | 263 | 256 | 0.38% | 6 | 41 | Township |
| Deepwater | 21 | 261 | 252 | 1.16% | 7 | 36 | Township |
| Davis | 22 | 239 | 232 | 0.42% | 7 | 33 | Township |
| Honey Creek | 23 | 193 | 185 | 0.52% | 6 | 30 | Township |
| Bear Creek | 24 | 147 | 142 | 0.68% | 4 | 36 | Township |
| Blairstown | 25 | 97 | 95 | 0% | 390 | 0 | City |
| Brownington | 26 | 72 | 69 | 0% | 595 | 0 | Town |
Clinton is the largest city in Henry County, with a population of 9,509.
Brownington is the smallest city in Henry County, with a population of 72.
There are 26 cities in Henry County, Missouri.