house
1/89
$5,451/mo
$829,0003bd·4ba·2,472sf
106 Queen Street S, Chestertown, MD 21620
Listing Courtesy of Chesapeake Real Estate Associates, LLC
Homes for Sale in Historic Chestertown, Chestertown, MD
1 active listing · 27 sold since 2020
1
For Sale
$530K
Median Sale Price
31
Median Days on Market
93.3%
Sold-to-List
$236
Price / Sq Ft
Newest homes for sale in Historic Chestertown, Chestertown, MD
See all 1 on the mapHistoric Chestertown, Chestertown, MD home price trend
| Year | Median Sale Price | Homes Sold |
|---|---|---|
| 2025 | $600K | 3 |
| 2024 | $725K | 7 |
| 2023 | $417K | 2 |
| 2022 | $634K | 4 |
| 2021 | $470K | 6 |
| 2020 | $346K | 5 |
At the current trend, the median is modeled to reach about $714K in 2026 (estimate).
Cost to buy in Historic Chestertown, Chestertown, MD
At today's ~6.75% 30-year rate, the median $530K home in Historic Chestertown, Chestertown, MD runs about $3,457/mo with 20% down (principal & interest plus estimated taxes and insurance).
Estimate only — not a loan offer. Actual rate and payment depend on your profile.
Top agents in Historic Chestertown, Chestertown, MD
Most active agents by closed sales here over the past 18 months.
- John J BurkeGunther-McClary Real Estate1 sale
- Andrea S AlderdiceLong & Foster Real Estate, Inc.1 sale
- Peter D HellerColdwell Banker Chesapeake Real Estate Company1 sale
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Historic Chestertown, Chestertown, MD real estate FAQ
How many homes are for sale in Historic Chestertown, Chestertown, MD?
There is 1 home currently for sale in Historic Chestertown, Chestertown, MD.
How much do homes sell for in Historic Chestertown, Chestertown, MD?
The median sale price in Historic Chestertown, Chestertown, MD is $530K, based on 27 sales since 2020 (ranging from $281K to $861K).
How fast do homes sell in Historic Chestertown, Chestertown, MD?
Homes in Historic Chestertown, Chestertown, MD typically go under contract in about 31 days on market (median).
Do homes in Historic Chestertown, Chestertown, MD sell above asking?
Over the past 12 months, homes in Historic Chestertown, Chestertown, MD sold for an average of 93.3% of list price — below asking.
What is the price per square foot in Historic Chestertown, Chestertown, MD?
Homes in Historic Chestertown, Chestertown, MD have sold for a median of $236 per square foot since 2020.
Is the Historic Chestertown, Chestertown, MD housing market heating up or cooling down?
The median sale price in Historic Chestertown, Chestertown, MD has risen from $346K in 2020 to $600K in 2025. At the current trend, the median is on track for roughly $714K in 2026 (modeled estimate).
Who are the top real estate agents in Historic Chestertown, Chestertown, MD?
The most active agents in Historic Chestertown, Chestertown, MD over the past 18 months are: John J Burke (Gunther-McClary Real Estate) — 1 sale; Andrea S Alderdice (Long & Foster Real Estate, Inc.) — 1 sale; Peter D Heller (Coldwell Banker Chesapeake Real Estate Company) — 1 sale.