23 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Denton | 1 | 5,100 | 4,843 | 1.01% | 968 | 5 | Town |
| Denton | 2 | 5,100 | 4,845 | 1.01% | 968 | 5 | Town |
| Federalsburg | 3 | 2,881 | 2,837 | 0.35% | 1,493 | 2 | Town |
| Federalsburg | 4 | 2,881 | 2,831 | 0.35% | 1,493 | 2 | Town |
| Greensboro | 5 | 1,983 | 1,916 | 0.71% | 1,846 | 1 | Town |
| Greensboro | 6 | 1,983 | 1,913 | 0.71% | 1,846 | 1 | Town |
| Ridgely | 7 | 1,654 | 1,614 | 0.49% | 887 | 2 | Town |
| Ridgely | 8 | 1,654 | 1,612 | 0.49% | 887 | 2 | Town |
| Preston | 9 | 691 | 676 | 0.44% | 1,259 | 1 | Town |
| Preston | 10 | 691 | 675 | 0.44% | 1,259 | 1 | Town |
| Goldsboro | 11 | 216 | 213 | 0% | 276 | 1 | Town |
| Goldsboro | 12 | 216 | 213 | 0% | 276 | 1 | Town |
| Marydel | 13 | 178 | 176 | 0% | 1,508 | 0 | Town |
| Marydel | 14 | 178 | 176 | 0% | 1,508 | 0 | Town |
| Henderson | 15 | 161 | 159 | 0% | 1,288 | 0 | Town |
| Henderson | 16 | 161 | 159 | 0% | 1,288 | 0 | Town |
| Williston | 17 | 153 | 174 | 0% | 582 | 0 | CDP |
| Hillsboro | 18 | 135 | 135 | 0% | 1,000 | 0 | Town |
| Hillsboro | 19 | 135 | 135 | 0% | 1,000 | 0 | Town |
| Templeville | 20 | 114 | 114 | 0% | 2,073 | 0 | Town |
| Templeville | 21 | 114 | 114 | 0% | 2,073 | 0 | Town |
| Choptank | 22 | 79 | 30 | -3.66% | 332 | 0 | CDP |
| West Denton | 23 | 61 | 14 | 7.02% | 210 | 0 | CDP |
Denton is the largest city in Caroline County, with a population of 5,100.
West Denton is the smallest city in Caroline County, with a population of 61.
There are 23 cities in Caroline County, Maryland.