Chestertown MD
222 active listings out of 6.5K total properties we track across 8 Chestertown ZIPs — listings, off-market homes, rentals, and full sales/tax history. Refreshed nightly.
Download Chestertown, MD property data
2,342,516 property records for all of Maryland — address, beds/baths, sqft, year built, status, list and last-sale price, price and tax history. Parquet or CSV.
Files are published by ZIP, county and state; this city is inside the state file.
Monthly snapshot · 255.7 MB Parquet · CSV (421.7 MB)
Records keep changing after a snapshot is compiled.
Rebuilt every day · same columns, same file layout
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 222 currently-active listings in Chestertown, MD. Full dataset covers 6.5K 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": 6477,
"active": 222,
"median_list": 350000
}Chestertown, MD real estate: market summary
As of November 2026, Straply tracks 6,477 homes in Chestertown, MD, with 222 active for sale at a median list price of $350,000 (~$237/sq ft). Notably, the market is cooling — the median sale price is down 11% year over year.
- Median list price
- $350,000
- Median $/sq ft
- $237
- Active listings
- 222
- Median sale price
- $339,500 (-11% YoY)
- Properties tracked
- 6,477
Frequently asked: Chestertown, MD real estate
What is the median home price in Chestertown?
The median list price in Chestertown, MD is $350,000 (about $237 per square foot), based on 222 active listings tracked by Straply as of November 2026.
What price range are homes in Chestertown?
Active listings in Chestertown, MD concentrate in: 39% under $300k and 32% $300k–$500k.
Are home prices in Chestertown going up or down?
The median sale price is $339,500, down 11% year over year. Straply tracked 204 sales here over the past 12 months.
How many homes are for sale in Chestertown?
Straply is tracking 222 active listings in Chestertown, MD out of 6,477 properties on record as of November 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 (59% of listings). Also common: lots / land 22%, townhouses 10%.
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 November 2026. Source: Straply. For address-level history and programmatic access, use the Straply API.