Performance indicators for the Chestertown short-term rental market based on reliable data.
Listings
Reliable / Active
Cap Rate
Middle-Earners Gross Yield
Revenue
Middle-Earners Revenue
Occupancy
Middle-Earners Occupancy
Home Value
Median Home Sale Price
Top Earners
Top-Earners Revenue
The highest-performing listings in Chestertown.
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Challenging to Investors
Short-term rentals are explicitly prohibited for ADUs in residential districts, and the town lacks a clear town-wide STR licensing framework, leaving principal dwellings to rely on a county license plus 5% county and ~6% state hotel taxes. This ambiguity, coupled with strict performance standards (owner-occupancy, 90‑day minimum for ADUs) and potential inconsistent enforcement, creates meaningful compliance risk and constraints for investors.
Local STR Agent
STR specialist · Chestertown, MD
Chestertown is a town in Kent County, Maryland, United States. The population was 5,252 as of the 2010 census. It is the county seat of Kent County.