43 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 |
| Oak Hill | 18 | 6,750 | 4,783 | 7.14% | 1,203 | 6 | CDP |
| Bridgton | 19 | 6,076 | 5,423 | 3.05% | 107 | 57 | Town |
| New Gloucester | 20 | 5,929 | 5,690 | 1.16% | 126 | 47 | Town |
| North Windham | 21 | 5,680 | 5,651 | 0.92% | 844 | 7 | CDP |
| Harpswell | 22 | 5,092 | 5,023 | 0.35% | 211 | 24 | Town |
| Raymond | 23 | 4,699 | 4,556 | 0.79% | 142 | 33 | Town |
| North Yarmouth | 24 | 4,400 | 4,099 | 0.87% | 207 | 21 | Town |
| Naples | 25 | 4,124 | 3,926 | 1.53% | 130 | 32 | Town |
| Casco | 26 | 3,777 | 3,642 | 0.96% | 121 | 31 | Town |
| Cumberland Center | 27 | 3,016 | 2,944 | 1.14% | 713 | 4 | CDP |
| Harrison | 28 | 2,630 | 2,455 | 1.62% | 79 | 33 | Town |
| Steep Falls | 29 | 2,324 | 2,016 | 3.52% | 232 | 10 | CDP |
| Dunstan | 30 | 2,152 | 1,592 | 7.12% | 681 | 3 | CDP |
| Falmouth Foreside | 31 | 2,150 | 1,550 | 2.04% | 1,413 | 2 | CDP |
| Sebago | 32 | 1,989 | 1,913 | 1.02% | 61 | 33 | Town |
| Baldwin | 33 | 1,665 | 1,520 | 2.34% | 47 | 35 | Town |
| Pownal | 34 | 1,649 | 1,574 | 1.54% | 72 | 23 | Town |
| Little Falls | 35 | 937 | 745 | 1.63% | 815 | 1 | CDP |
| South Windham | 36 | 699 | 1,022 | -6.05% | 585 | 1 | CDP |
| Cousins Island | 37 | 508 | 521 | 0.4% | 479 | 1 | CDP |
| Naples | 38 | 447 | 555 | 0.22% | 173 | 3 | CDP |
| Chebeague Island | 39 | 403 | 397 | 0.5% | 113 | 4 | Town |
| Standish | 40 | 235 | 198 | -6.37% | 88 | 3 | CDP |
| Long Island | 41 | 232 | 235 | -0.43% | 162 | 1 | Town |
| Littlejohn Island | 42 | 43 | 63 | -10.42% | 126 | 0 | CDP |
| Frye Island | 43 | 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 43 cities in Cumberland County, Maine.