26 cities
| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Clinton | 1 | 9,569 | 9,209 | 0.63% | 1,050 | 9 | City |
| Clinton | 2 | 9,058 | 8,757 | 0.43% | 260 | 35 | Township |
| Windsor | 3 | 3,465 | 3,333 | 0.49% | 98 | 35 | Township |
| Windsor | 4 | 2,895 | 2,772 | 0.73% | 1,197 | 2 | City |
| Fields Creek | 5 | 1,781 | 1,723 | 0.45% | 57 | 31 | Township |
| Clinton | 6 | 1,600 | 1,507 | 0.44% | 24 | 65 | Township |
| Leesville | 7 | 1,079 | 1,032 | 0.65% | 26 | 42 | Township |
| Osage | 8 | 800 | 765 | 0.76% | 20 | 39 | Township |
| Tebo | 9 | 767 | 747 | 0.39% | 16 | 47 | Township |
| White Oak | 10 | 764 | 740 | 0.53% | 24 | 32 | Township |
| Bethlehem | 11 | 723 | 690 | 0.84% | 17 | 43 | Township |
| Deepwater | 12 | 603 | 585 | 0.5% | 17 | 36 | Township |
| Urich | 13 | 480 | 467 | 0.42% | 1,188 | 0 | City |
| Deer Creek | 14 | 458 | 444 | 0.44% | 14 | 33 | Township |
| Shawnee | 15 | 446 | 432 | 0.45% | 11 | 42 | Township |
| Calhoun | 16 | 409 | 396 | 0.49% | 416 | 1 | City |
| Deepwater | 17 | 397 | 358 | 1.79% | 468 | 1 | City |
| Montrose | 18 | 395 | 385 | 0.51% | 693 | 1 | City |
| Creighton | 19 | 334 | 327 | 0.3% | 968 | 0 | City |
| Deepwater | 20 | 264 | 252 | 1.15% | 7 | 36 | Township |
| Big Creek | 21 | 264 | 256 | 0.38% | 6 | 41 | Township |
| Davis | 22 | 240 | 232 | 0.42% | 7 | 33 | Township |
| Honey Creek | 23 | 194 | 185 | 0.52% | 6 | 30 | Township |
| Bear Creek | 24 | 148 | 142 | 0.68% | 4 | 36 | Township |
| Blairstown | 25 | 98 | 95 | 1.03% | 394 | 0 | City |
| Brownington | 26 | 73 | 69 | 1.39% | 603 | 0 | Town |
Clinton is the largest city in Henry County, with a population of 9,569.
Brownington is the smallest city in Henry County, with a population of 73.
There are 26 cities in Henry County, Missouri.