Chestertown, MD vs Westernport, MD

The cost of living difference between Chestertown, MD and Westernport, MD is dramatic. Westernport is 47.4% cheaper than Chestertown, a gap that translates to thousands of dollars per year in household expenses. Chestertown has a cost index of 97 while Westernport sits at 66, making this one of the more striking comparisons on our site. Relocating between these cities would require a serious reassessment of budget and lifestyle expectations.

On the housing front, median rent in Chestertown is $1,090/month compared to $727/month in Westernport — a 50% difference. Home values follow the same pattern: Westernport is more affordable at $85,800 median vs $333,900.

Median household income in Chestertown is $47,047 compared to $52,059 in Westernport (-9.6%). Westernport offers a double advantage: higher earnings combined with a lower cost of living, giving residents significantly more purchasing power. Looking at affordability, residents of Chestertown spend roughly 27.8% of their income on rent, more than the 16.8% in Westernport.

Climate-wise, Chestertown is notably warmer with an average of 55.2°F compared to 46.5°F in Westernport. Westernport receives more rainfall at 56.7" per year compared to 47.1" in Chestertown.