Chestertown MD
111 active listings out of 6K total properties we track across 7 Chestertown ZIPs — listings, off-market homes, rentals, and full sales/tax history. Refreshed nightly.
While you're here, take in the bigger picture — maps below show Maryland (statewide), not just Chestertown. Same company, same dataset, different resolution.
Inventory breakdown
Distribution of the 111 currently-active listings in Chestertown, MD. Full dataset covers 6K properties — listings, off-market homes, rentals, and full history.
ZIP codes in Chestertown
Drill into any ZIP for hex-level breakdowns.
Nearby cities
Other Maryland cities within driving distance.
Get Chestertown, MD data in your app
GET https://api.straply.com/v1/markets/city/chestertown-md
Authorization: Bearer $STRAPLY_KEY{
"city": "chestertown-md",
"total_tracked": 5993,
"active": 111,
"median_list": 425000
}Chestertown, MD real estate: market summary
As of April 2026, Straply tracks 5,993 homes in Chestertown, MD, with 111 active for sale at a median list price of $425,000 (~$231/sq ft). Notably, most homes were built in the 2000s.
- Median list price
- $425,000
- Median $/sq ft
- $231
- Active listings
- 111
- Median sale price
- $487,500
- Properties tracked
- 5,993
Frequently asked: Chestertown, MD real estate
What is the median home price in Chestertown?
The median list price in Chestertown, MD is $425,000 (about $231 per square foot), based on 111 active listings tracked by Straply as of April 2026.
What price range are homes in Chestertown?
Active listings in Chestertown, MD concentrate in: 42% $300k–$500k and 21% under $300k.
How many homes are for sale in Chestertown?
Straply is tracking 111 active listings in Chestertown, MD out of 5,993 properties on record as of April 2026.
How old are the homes in Chestertown?
Most homes in Chestertown, MD were built in the 2000s. About 48% were built after 1980, while 17% predate 1940. The newest tracked home dates to 2026.
What types of homes are in Chestertown?
Chestertown, MD is mostly single-family homes (71% of listings). Also common: condos 13%, townhouses 12%.
How many bedrooms do homes in Chestertown typically have?
The most common size in Chestertown, MD is 3 bd.
What areas are near Chestertown?
Nearby markets Straply also tracks include Worton, Church Hill, Rock Hall, Kennedyville.
Data as of April 2026. Source: Straply. For address-level history and programmatic access, use the Straply API.