10 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Oak Bluffs town | 1 | 5,265 | 5,330 | -0.85% | 722 | 7.29 | Town |
| Edgartown town | 2 | 5,228 | 5,171 | -0.38% | 195 | 26.81 | Town |
| Tisbury town | 3 | 4,775 | 4,817 | -0.93% | 732 | 6.52 | Town |
| West Tisbury town | 4 | 3,542 | 3,550 | -0.62% | 142 | 25.03 | Town |
| Vineyard Haven | 5 | 2,430 | 1,903 | 0.87% | 1,863 | 1.30 | CDP |
| Oak Bluffs | 6 | 1,901 | 1,745 | 7.16% | 1,050 | 1.81 | CDP |
| Chilmark town | 7 | 1,222 | 1,212 | -0.41% | 64 | 19.04 | Town |
| Edgartown | 8 | 763 | 517 | 7.16% | 638 | 1.20 | CDP |
| Aquinnah town | 9 | 436 | 445 | -1.13% | 82 | 5.33 | Town |
| Gosnold town | 10 | 65 | 68 | -1.52% | 5 | 13.19 | Town |
Oak Bluffs town is the largest city in Dukes County, with a population of 5,265.
Gosnold town is the smallest city in Dukes County.
There are 10 cities in Dukes County, Massachusetts.