| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Denton | 1 | 5,123 | 4,845 | 0.95% | 973 | 5 | Town |
| Federalsburg | 2 | 2,871 | 2,833 | 0.24% | 1,488 | 2 | Town |
| Greensboro | 3 | 1,973 | 1,910 | 0.56% | 1,837 | 1 | Town |
| Ridgely | 4 | 1,636 | 1,610 | 0.37% | 878 | 2 | Town |
| Preston | 5 | 686 | 674 | 0.29% | 1,250 | 1 | Town |
| Goldsboro | 6 | 215 | 211 | 0% | 275 | 1 | Town |
| Marydel | 7 | 177 | 176 | 0% | 1,500 | 0 | Town |
| Henderson | 8 | 161 | 160 | 0% | 1,288 | 0 | Town |
| Hillsboro | 9 | 132 | 134 | -0.75% | 978 | 0 | Town |
| Templeville | 10 | 118 | 115 | 0.85% | 2,145 | 0 | Town |
Denton is the largest city in Caroline County, with a population of 5,123.
Templeville is the smallest city in Caroline County, with a population of 118.
There are 10 cities in Caroline County, Maryland.