Chestertown, MD Real Estate & Homes For Sale
115 homes
- NEWNEW CONSTRUCTIONBUILDABLE PLAN$419,990+4 Beds3.5 Baths2,397 sqftAllegheny | Finished Basement Plan in Radcliffe Meadows Single Family Homes,
Chestertown, MD 21620 - NEWNEW CONSTRUCTIONBUILDABLE PLAN$369,990+3 Beds2 Baths2,158 sqftRosecliff | Finished Basement Plan in Radcliffe Meadows Villas,
Chestertown, MD 21620 - NEWNEW CONSTRUCTIONBUILDABLE PLAN$449,990+4 Beds2.5 Baths3,133 sqftColumbia | Finished Basement Plan in Radcliffe Meadows Single Family Homes,
Chestertown, MD 21620 - OPEN SAT, 11-1PM1.84 ACRESBenson & Mangold, LLC
- NEW0.65 ACRESColdwell Banker Chesapeake Real Estate Company
- AUCTION0.37 ACRES
- 3D VIEW0.46 ACRESDoug Ashley Realtors, LLC
- Doug Ashley Realtors, LLC
- Cross Street Realtors LLC
- Douglas Realty LLC
- $399,990+3 Beds2.5 Baths2,603 sqftCaroline | Finished Basement Plan in Radcliffe Meadows Villas,
Chestertown, MD 21620 - $484,990+3 Beds2.5 Baths3,176 sqftAnderson | Finished Basment Plan in Radcliffe Meadows Single Family Homes,
Chestertown, MD 21620 - $439,990+2 Beds2 Baths2,346 sqftAlberti Ranch | Finished Basement Plan in Radcliffe Meadows Single Family Homes,
Chestertown, MD 21620 - $464,990+2 Beds2 Baths2,642 sqftBramante Ranch | Finished Basement Plan in Radcliffe Meadows Single Family Homes,
Chestertown, MD 21620 - $499,990+3 Beds3 Baths3,301 sqftBramante 2-Story | Finished Basement Plan in Radcliffe Meadows Single Family Homes,
Chestertown, MD 21620 - Coldwell Banker Chesapeake Real Estate Company
- RE/MAX Advantage Realty
- Gunther-McClary Real Estate
- Real Broker, LLC
- Chesapeake Real Estate Associates, LLC
- Coldwell Banker Chesapeake Real Estate Company
- Cross Street Realtors LLC
- Benson & Mangold, LLC
- Coldwell Banker Chesapeake Real Estate Company
- Doug Ashley Realtors, LLC
- Coldwell Banker Chesapeake Real Estate Company
- Cross Street Realtors LLC
- Doug Ashley Realtors, LLC
- TTR Sotheby's International Realty
- Real Broker, LLC
- Chesapeake Real Estate Associates, LLC
- Doug Ashley Realtors, LLC
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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 |
|---|---|
| October 2025 | $380k |
| November 2025 | $381k |
| December 2025 | $382k |
| January 2026 | $383k |
| February 2026 | $384k |
| March 2026 | $385k |
| April 2026 | $386k |
| May 2026 | $386k |
| June 2026 | $385k |
| July 2026 | $386k |
| August 2026 | $387k |
| September 2026 | $387k |
Trends and affordability stats are provided by third party data sources.
Average Home Value in Chestertown, MD, by Home Size
Currently, there are 11 new listings in Chestertown, MD and 115 homes for sale.
| Home Size | Home Value* |
|---|---|
| 2 bedrooms (8 homes) | $296,838 |
| 3 bedrooms (40 homes) | $359,683 |
| 4 bedrooms (12 homes) | $487,408 |
Explore Neighborhoods in Chestertown, MD
Neighborhood stats provided by third party data sources.
What Locals Say about Chestertown
Browse Chestertown, MD homes by type

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.
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