26 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Clinton | 1 | 9,554 | 9,209 | 0.73% | 1,048 | 9 | City |
| Clinton | 2 | 8,995 | 8,761 | 0.22% | 258 | 35 | Township |
| Windsor | 3 | 3,462 | 3,333 | 0.64% | 98 | 35 | Township |
| Windsor | 4 | 2,890 | 2,775 | 0.8% | 1,195 | 2 | City |
| Fields Creek | 5 | 1,768 | 1,719 | 0.28% | 57 | 31 | Township |
| Clinton | 6 | 1,611 | 1,507 | 1% | 25 | 65 | Township |
| Leesville | 7 | 1,061 | 1,031 | 0.19% | 25 | 42 | Township |
| Osage | 8 | 787 | 765 | 0.25% | 20 | 39 | Township |
| Tebo | 9 | 765 | 748 | 0.26% | 16 | 47 | Township |
| White Oak | 10 | 757 | 740 | 0.26% | 24 | 32 | Township |
| Bethlehem | 11 | 711 | 690 | 0.28% | 16 | 43 | Township |
| Deepwater | 12 | 593 | 584 | 0% | 17 | 36 | Township |
| Urich | 13 | 477 | 466 | 0.42% | 1,181 | 0 | City |
| Deer Creek | 14 | 456 | 445 | 0.22% | 14 | 33 | Township |
| Shawnee | 15 | 439 | 431 | 0% | 11 | 42 | Township |
| Calhoun | 16 | 407 | 397 | 0.49% | 414 | 1 | City |
| Montrose | 17 | 392 | 384 | 0.51% | 688 | 1 | City |
| Deepwater | 18 | 385 | 357 | 1.58% | 454 | 1 | City |
| Creighton | 19 | 324 | 329 | -0.31% | 939 | 0 | City |
| Big Creek | 20 | 262 | 254 | 0.38% | 6 | 41 | Township |
| Deepwater | 21 | 254 | 249 | 0.4% | 7 | 36 | Township |
| Davis | 22 | 237 | 232 | 0% | 7 | 33 | Township |
| Honey Creek | 23 | 188 | 184 | 0% | 6 | 30 | Township |
| Bear Creek | 24 | 144 | 141 | 0% | 4 | 36 | Township |
| Blairstown | 25 | 98 | 95 | 1.03% | 394 | 0 | City |
| Brownington | 26 | 72 | 69 | 1.41% | 595 | 0 | Town |
Clinton is the largest city in Henry County, with a population of 9,554.
Brownington is the smallest city in Henry County, with a population of 72.
There are 26 cities in Henry County, Missouri.