Homes for Sale in Downtown Chestertown, Chestertown, MD
No homes on the market right now — but 34 have sold here since 2020. Homes move fast; get notified first.
0
For Sale
$294K
Median Sale Price
31
Median Days on Market
100.0%
Sold-to-List
$185
Price / Sq Ft
Downtown Chestertown, Chestertown, MD home price trend
| Year | Median Sale Price | Homes Sold |
|---|---|---|
| 2026 | $650K | 1 |
| 2025 | $764K | 2 |
| 2024 | $374K | 5 |
| 2023 | $300K | 2 |
| 2022 | $354K | 5 |
| 2021 | $230K | 12 |
| 2020 | $150K | 7 |
At the current trend, the median is modeled to reach about $773K in 2027 (estimate).
Cost to buy in Downtown Chestertown, Chestertown, MD
At today's ~6.63% 30-year rate, the median $294K home in Downtown Chestertown, Chestertown, MD runs about $1,901/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 Downtown Chestertown, Chestertown, MD
Most active agents by closed sales here over the past 18 months.
- Richard KeaveneyCross Street Realtors LLC2 sales
- Jennifer L MobleyColdwell Banker Chesapeake Real Estate Company1 sale
Be first when a home hits the market in Downtown Chestertown, Chestertown, MD
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Downtown Chestertown, Chestertown, MD real estate FAQ
How many homes are for sale in Downtown Chestertown, Chestertown, MD?
There are no homes for sale in Downtown Chestertown, Chestertown, MD right now. 34 have sold here since 2020 — the market moves fast, so set up an alert to hear the moment one is listed.
How much do homes sell for in Downtown Chestertown, Chestertown, MD?
The median sale price in Downtown Chestertown, Chestertown, MD is $294K, based on 34 sales since 2020 (ranging from $96K to $647K).
How fast do homes sell in Downtown Chestertown, Chestertown, MD?
Homes in Downtown Chestertown, Chestertown, MD typically go under contract in about 31 days on market (median).
Do homes in Downtown Chestertown, Chestertown, MD sell above asking?
Over the past 12 months, homes in Downtown Chestertown, Chestertown, MD sold for an average of 100.0% of list price — at or above asking.
What is the price per square foot in Downtown Chestertown, Chestertown, MD?
Homes in Downtown Chestertown, Chestertown, MD have sold for a median of $185 per square foot since 2020.
Is the Downtown Chestertown, Chestertown, MD housing market heating up or cooling down?
The median sale price in Downtown Chestertown, Chestertown, MD has risen from $150K in 2020 to $650K in 2026. At the current trend, the median is on track for roughly $773K in 2027 (modeled estimate).
Who are the top real estate agents in Downtown Chestertown, Chestertown, MD?
The most active agents in Downtown Chestertown, Chestertown, MD over the past 18 months are: Richard Keaveney (Cross Street Realtors LLC) — 2 sales; Jennifer L Mobley (Coldwell Banker Chesapeake Real Estate Company) — 1 sale.