13 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Denton | 1 | 5,069 | 4,844 | 0.9% | 962 | 5.27 | Town |
| Federalsburg | 2 | 2,789 | 2,826 | -0.25% | 1,445 | 1.93 | Town |
| Greensboro | 3 | 1,930 | 1,917 | 0.16% | 1,797 | 1.07 | Town |
| Ridgely | 4 | 1,611 | 1,611 | 0% | 864 | 1.86 | Town |
| Preston | 5 | 676 | 675 | 0% | 1,231 | 0.55 | Town |
| Goldsboro | 6 | 209 | 211 | 0% | 267 | 0.78 | Town |
| Marydel | 7 | 172 | 174 | 0% | 1,458 | 0.12 | Town |
| Henderson | 8 | 160 | 160 | 0% | 1,280 | 0.13 | Town |
| Williston | 9 | 153 | 174 | 0% | 582 | 0.26 | CDP |
| Hillsboro | 10 | 131 | 135 | -0.76% | 970 | 0.14 | Town |
| Templeville | 11 | 120 | 114 | 0.84% | 2,182 | 0.06 | Town |
| Choptank | 12 | 79 | 30 | -3.66% | 332 | 0.24 | CDP |
| West Denton | 13 | 61 | 14 | 7.02% | 210 | 0.29 | CDP |
Denton is the largest city in Caroline County, with a population of 5,069.
West Denton is the smallest city in Caroline County.
There are 13 cities in Caroline County, Maryland.