The median sales price for homes in Chestertown MD for Aug 13 to Nov 13 was $236,000. This represents an increase of 37.2%, or $64,000, compared to the prior quarter and an increase of 6.3% compared to the prior year. Sales prices have depreciated 5.6% over the last 5 years in Chestertown. The average listing price for Chestertown homes for sale on Trulia was $455,115 for the week ending Nov 27, which represents a decline of 5.2%, or $24,952, compared to the prior week and an increase of 4.9%, or $21,065, compared to the week ending Nov 06. Average price per square foot for Chestertown MD was $144, an increase of 2.1% compared to the same period last year.