52 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Clinton | 1 | 9,509 | 9,196 | 0.63% | 1,043 | 9 | City |
| Clinton | 2 | 9,509 | 9,209 | 0.63% | 1,043 | 9 | City |
| Clinton | 3 | 9,019 | 8,744 | 0.43% | 259 | 35 | Township |
| Clinton | 4 | 9,019 | 8,757 | 0.43% | 259 | 35 | Township |
| Windsor | 5 | 3,448 | 3,330 | 0.5% | 97 | 35 | Township |
| Windsor | 6 | 3,448 | 3,333 | 0.5% | 97 | 35 | Township |
| Windsor | 7 | 2,874 | 2,770 | 0.7% | 1,188 | 2 | City |
| Windsor | 8 | 2,874 | 2,772 | 0.7% | 1,188 | 2 | City |
| Fields Creek | 9 | 1,773 | 1,721 | 0.45% | 57 | 31 | Township |
| Fields Creek | 10 | 1,773 | 1,723 | 0.45% | 57 | 31 | Township |
| Clinton | 11 | 1,593 | 1,509 | 0.44% | 24 | 65 | Township |
| Clinton | 12 | 1,593 | 1,507 | 0.44% | 24 | 65 | Township |
| Leesville | 13 | 1,072 | 1,030 | 0.66% | 26 | 42 | Township |
| Leesville | 14 | 1,072 | 1,032 | 0.66% | 26 | 42 | Township |
| Osage | 15 | 794 | 764 | 0.76% | 20 | 39 | Township |
| Osage | 16 | 794 | 765 | 0.76% | 20 | 39 | Township |
| Tebo | 17 | 764 | 745 | 0.39% | 16 | 47 | Township |
| Tebo | 18 | 764 | 747 | 0.39% | 16 | 47 | Township |
| White Oak | 19 | 760 | 739 | 0.53% | 24 | 32 | Township |
| White Oak | 20 | 760 | 740 | 0.53% | 24 | 32 | Township |
| Bethlehem | 21 | 717 | 689 | 0.84% | 17 | 43 | Township |
| Bethlehem | 22 | 717 | 690 | 0.84% | 17 | 43 | Township |
| Deepwater | 23 | 600 | 584 | 0.5% | 17 | 36 | Township |
| Deepwater | 24 | 600 | 585 | 0.5% | 17 | 36 | Township |
| Urich | 25 | 478 | 466 | 0.42% | 1,183 | 0 | City |
| Urich | 26 | 478 | 467 | 0.42% | 1,183 | 0 | City |
| Deer Creek | 27 | 456 | 443 | 0.44% | 14 | 33 | Township |
| Deer Creek | 28 | 456 | 444 | 0.44% | 14 | 33 | Township |
| Shawnee | 29 | 444 | 431 | 0.45% | 11 | 42 | Township |
| Shawnee | 30 | 444 | 432 | 0.45% | 11 | 42 | Township |
| Calhoun | 31 | 407 | 395 | 0.49% | 414 | 1 | City |
| Calhoun | 32 | 407 | 396 | 0.49% | 414 | 1 | City |
| Montrose | 33 | 393 | 384 | 0.26% | 689 | 1 | City |
| Montrose | 34 | 393 | 385 | 0.26% | 689 | 1 | City |
| Deepwater | 35 | 390 | 357 | 1.56% | 460 | 1 | City |
| Deepwater | 36 | 390 | 358 | 1.56% | 460 | 1 | City |
| Creighton | 37 | 333 | 325 | 0.3% | 965 | 0 | City |
| Creighton | 38 | 333 | 327 | 0.3% | 965 | 0 | City |
| Big Creek | 39 | 263 | 256 | 0.38% | 6 | 41 | Township |
| Big Creek | 40 | 263 | 256 | 0.38% | 6 | 41 | Township |
| Deepwater | 41 | 261 | 252 | 1.16% | 7 | 36 | Township |
| Deepwater | 42 | 261 | 252 | 1.16% | 7 | 36 | Township |
| Davis | 43 | 239 | 232 | 0.42% | 7 | 33 | Township |
| Davis | 44 | 239 | 232 | 0.42% | 7 | 33 | Township |
| Honey Creek | 45 | 193 | 185 | 0.52% | 6 | 30 | Township |
| Honey Creek | 46 | 193 | 185 | 0.52% | 6 | 30 | Township |
| Bear Creek | 47 | 147 | 142 | 0.68% | 4 | 36 | Township |
| Bear Creek | 48 | 147 | 142 | 0.68% | 4 | 36 | Township |
| Blairstown | 49 | 97 | 95 | 0% | 390 | 0 | City |
| Blairstown | 50 | 97 | 95 | 0% | 390 | 0 | City |
| Brownington | 51 | 72 | 69 | 0% | 595 | 0 | Town |
| Brownington | 52 | 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 52 cities in Henry County, Missouri.