31 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Portland | 1 | 69,836 | 68,496 | 0.39% | 3,242 | 22 | City |
| Portland | 2 | 69,769 | 68,496 | 0.29% | 3,239 | 22 | City |
| South Portland | 3 | 27,097 | 26,581 | 0.38% | 2,250 | 12 | City |
| South Portland | 4 | 27,038 | 26,581 | 0.16% | 2,245 | 12 | City |
| Scarborough | 5 | 24,230 | 22,245 | 0.92% | 507 | 48 | Town |
| Brunswick | 6 | 22,691 | 21,763 | 0.27% | 485 | 47 | Town |
| Westbrook | 7 | 22,079 | 20,435 | 3.24% | 1,284 | 17 | City |
| Westbrook | 8 | 21,623 | 20,435 | 1.11% | 1,258 | 17 | City |
| Windham | 9 | 19,954 | 18,491 | 1.34% | 428 | 47 | Town |
| Gorham | 10 | 18,591 | 18,364 | 0.25% | 367 | 51 | Town |
| Falmouth | 11 | 12,925 | 12,475 | 0.05% | 440 | 29 | Town |
| Standish | 12 | 11,011 | 10,241 | 1.05% | 186 | 59 | Town |
| Cape Elizabeth | 13 | 9,754 | 9,539 | 0.68% | 657 | 15 | Town |
| Yarmouth | 14 | 9,068 | 8,998 | 0.09% | 676 | 13 | Town |
| Freeport | 15 | 8,935 | 8,741 | 0.65% | 257 | 35 | Town |
| Cumberland | 16 | 8,895 | 8,469 | 0.71% | 389 | 23 | Town |
| Gray | 17 | 8,725 | 8,287 | 1.65% | 202 | 43 | Town |
| Bridgton | 18 | 6,076 | 5,423 | 3.05% | 107 | 57 | Town |
| New Gloucester | 19 | 5,929 | 5,690 | 1.16% | 126 | 47 | Town |
| Harpswell | 20 | 5,092 | 5,023 | 0.35% | 211 | 24 | Town |
| Raymond | 21 | 4,699 | 4,556 | 0.79% | 142 | 33 | Town |
| North Yarmouth | 22 | 4,400 | 4,099 | 0.87% | 207 | 21 | Town |
| Naples | 23 | 4,124 | 3,926 | 1.53% | 130 | 32 | Town |
| Casco | 24 | 3,777 | 3,642 | 0.96% | 121 | 31 | Town |
| Harrison | 25 | 2,630 | 2,455 | 1.62% | 79 | 33 | Town |
| Sebago | 26 | 1,989 | 1,913 | 1.02% | 61 | 33 | Town |
| Baldwin | 27 | 1,665 | 1,520 | 2.34% | 47 | 35 | Town |
| Pownal | 28 | 1,649 | 1,574 | 1.54% | 72 | 23 | Town |
| Chebeague Island | 29 | 403 | 397 | 0.5% | 113 | 4 | Town |
| Long Island | 30 | 232 | 235 | -0.43% | 162 | 1 | Town |
| Frye Island | 31 | 30 | 28 | 3.45% | 22 | 1 | Town |
Portland is the largest city in Cumberland County, with a population of 69,836.
Frye Island is the smallest city in Cumberland County, with a population of 30.
There are 31 cities in Cumberland County, Maine.