Homes for Sale in Historic District Chestertown, Chestertown, MD
No homes on the market right now — but 18 have sold here since 2020. Homes move fast; get notified first.
0
For Sale
$393K
Median Sale Price
16
Median Days on Market
89.9%
Sold-to-List
$216
Price / Sq Ft
Historic District Chestertown, Chestertown, MD home price trend
| Year | Median Sale Price | Homes Sold |
|---|---|---|
| 2025 | $490K | 5 |
| 2024 | $255K | 1 |
| 2023 | $625K | 2 |
| 2022 | $365K | 3 |
| 2021 | $270K | 5 |
| 2020 | $385K | 2 |
At the current trend, the median is modeled to reach about $472K in 2026 (estimate).
Cost to buy in Historic District Chestertown, Chestertown, MD
At today's ~6.63% 30-year rate, the median $393K home in Historic District Chestertown, Chestertown, MD runs about $2,537/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 District Chestertown, Chestertown, MD
Most active agents by closed sales here over the past 18 months.
- Sarah E. KingCross Street Realtors LLC1 sale
- Elisabeth J OstranderDoug Ashley Realtors, LLC1 sale
- Richard KeaveneyCross Street Realtors LLC1 sale
- Nancy Mcd McguireMaryland Heritage Properties1 sale
- Michael OneillColdwell Banker Chesapeake Real Estate Company1 sale
Be first when a home hits the market in Historic District Chestertown, Chestertown, MD
Homes here sell fast and rarely come up. Turn on instant alerts and we'll email you the moment a new one is listed.
Historic District Chestertown, Chestertown, MD real estate FAQ
How many homes are for sale in Historic District Chestertown, Chestertown, MD?
There are no homes for sale in Historic District Chestertown, Chestertown, MD right now. 18 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 Historic District Chestertown, Chestertown, MD?
The median sale price in Historic District Chestertown, Chestertown, MD is $393K, based on 18 sales since 2020 (ranging from $130K to $749K).
How fast do homes sell in Historic District Chestertown, Chestertown, MD?
Homes in Historic District Chestertown, Chestertown, MD typically go under contract in about 16 days on market (median).
Do homes in Historic District Chestertown, Chestertown, MD sell above asking?
Over the past 12 months, homes in Historic District Chestertown, Chestertown, MD sold for an average of 89.9% of list price — below asking.
What is the price per square foot in Historic District Chestertown, Chestertown, MD?
Homes in Historic District Chestertown, Chestertown, MD have sold for a median of $216 per square foot since 2020.
Is the Historic District Chestertown, Chestertown, MD housing market heating up or cooling down?
The median sale price in Historic District Chestertown, Chestertown, MD has risen from $385K in 2020 to $490K in 2025. At the current trend, the median is on track for roughly $472K in 2026 (modeled estimate).
Who are the top real estate agents in Historic District Chestertown, Chestertown, MD?
The most active agents in Historic District Chestertown, Chestertown, MD over the past 18 months are: Sarah E. King (Cross Street Realtors LLC) — 1 sale; Elisabeth J Ostrander (Doug Ashley Realtors, LLC) — 1 sale; Richard Keaveney (Cross Street Realtors LLC) — 1 sale.