Chestertown, MD Real Estate & Homes For Sale
114 homes
- NEW - 2 HRS AGO5.17 ACRESGunther-McClary Real Estate
- NEW - 22 HRS AGO3D VIEW0.34 ACRESDoug Ashley Realtors, LLC
- NEWCOMING SOON 9/110.5 ACRESRE/MAX Executive
- NEWCOMING SOON 9/100.45 ACRESTaylor Properties
- NEWCOMING SOON 9/181.22 ACRESRE/MAX Chesapeake
- OPEN SAT, 10-12PM0.34 ACRESColdwell Banker Chesapeake Real Estate Company
- EXP Realty, LLC
- Coldwell Banker Chesapeake Real Estate Company
- Chesapeake Real Estate Associates, LLC
- Coldwell Banker Chesapeake Real Estate Company
- Cross Street Realtors LLC
- Doug Ashley Realtors, LLC
- Coldwell Banker Chesapeake Real Estate Company
- Cross Street Realtors LLC
- Coldwell Banker Chesapeake Real Estate Company
- Doug Ashley Realtors, LLC
- TTR Sotheby's International Realty
- Real Broker, LLC
- Chesapeake Real Estate Associates, LLC
- Doug Ashley Realtors, LLC
- Doug Ashley Realtors, LLC
- Elevated Real Estate Solutions
- Cross Street Realtors LLC
- Coldwell Banker Chesapeake Real Estate Company
- Real Broker, LLC
- Benson & Mangold, LLC
- TTR Sotheby's International Realty
Chestertown, MD Real Estate Trends
Learn about the Chestertown, MD housing market through trends and averages.Affordability of Living in Chestertown, MD
| Month | Median home value |
|---|---|
| August 2025 | $390k |
| September 2025 | $390k |
| October 2025 | $390k |
| November 2025 | $391k |
| December 2025 | $393k |
| January 2026 | $394k |
| February 2026 | $395k |
| March 2026 | $396k |
| April 2026 | $396k |
| May 2026 | $396k |
| June 2026 | $396k |
| July 2026 | $396k |
Trends and affordability stats are provided by third party data sources.
Average Home Value in Chestertown, MD, by Home Size
Currently, there are 12 new listings in Chestertown, MD and 114 homes for sale.
| Home Size | Home Value* |
|---|---|
| 2 bedrooms (6 homes) | $300,391 |
| 3 bedrooms (38 homes) | $366,474 |
| 4 bedrooms (14 homes) | $499,115 |
Explore Neighborhoods in Chestertown, MD
Neighborhood stats provided by third party data sources.
What Locals Say about Chestertown

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement.
Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale.
Property information displayed is deemed reliable but is not guaranteed.
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