10 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Oak Bluffs | 1 | 5,438 | 5,332 | 0.57% | 746 | 7 | Town |
| Edgartown | 2 | 5,370 | 5,171 | 0.79% | 200 | 27 | Town |
| Tisbury | 3 | 4,974 | 4,813 | 0.95% | 763 | 7 | Town |
| West Tisbury | 4 | 3,681 | 3,545 | 1.21% | 147 | 25 | Town |
| Vineyard Haven | 5 | 2,430 | 1,903 | 0.87% | 1,863 | 1 | CDP |
| Oak Bluffs | 6 | 1,901 | 1,745 | 7.16% | 1,050 | 2 | CDP |
| Chilmark | 7 | 1,261 | 1,214 | 0.96% | 66 | 19 | Town |
| Edgartown | 8 | 763 | 517 | 7.16% | 638 | 1 | CDP |
| Aquinnah | 9 | 456 | 443 | 1.11% | 86 | 5 | Town |
| Gosnold | 10 | 63 | 62 | 1.61% | 5 | 13 | Town |
Oak Bluffs is the largest city in Dukes County, with a population of 5,438.
Gosnold is the smallest city in Dukes County, with a population of 63.
There are 10 cities in Dukes County, Massachusetts.