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Featured local agent — Chestertown, NY
Sarah Mitchell
Compass Real Estate · Chestertown, NY
“Your trusted relocation specialist since 2009. 350+ homes sold. Zero-pressure, data-first approach.”
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Chestertown, NY Housing Market & Real Estate
Housing market overview · Updated monthly ·
$310,000median sale price
How is the Chestertown, NY housing market right now?
The median home sale price in Chestertown, NY is $310,000, down 7.5% year-over-year. Homes sell in an average of 61 days. The market is currently a buyer's market. (Source: Redfin monthly MLS data, as of December 2025 — the most recent Redfin release; Redfin publishes each month's data on a ~6-week lag.)
Is Chestertown a buyer's or seller's market?
Chestertown, NY is currently a buyer's market and homes selling in about 61 days. How we determine this →
Homes sold
1
Last 12 weeks
Days on market
61
Average pace
Active listings
—
Sale-to-list
95.4%
Below asking
What does the Chestertown housing market data show?
| Metric | Value |
|---|---|
| Median sale price | $310,000 |
| Year-over-year price change | -7.5% |
| Average days on market | 61 days |
| Sale-to-list price ratio | 95.4% |
| Median price per sq ft | $369/sq ft |
| Homes sold (latest month) | 1 |
| Market condition | Buyer's market |
Source: Redfin · Updated monthly
How much do homes cost in Chestertown by property type?
How the Chestertown, NY market breaks down across single-family homes, condos, and townhouses.
| Property type | Median price | Price / sq ft | Homes sold | Days on market |
|---|---|---|---|---|
| Single-family | $279,750 | $194/sq ft | 2 | 115 days |
| Condo / Co-op | $310,000 | $369/sq ft | 1 | 61 days |
| Townhouse | $335,000 | $169/sq ft | 1 | 110 days |
Source: Redfin · Updated monthly
The Chestertown housing market is currently classified as a buyer's market with a median sale price of $310,000. Prices have fallen 7.5% compared to last year, with homes spending an average of 61 days on market.This inventory level gives buyers significantly more negotiating power, allowing time to inspect properties thoroughly and potentially negotiate better terms.The price-to-income ratio of 6.1x provides context for how home values compare to local earning capacity.
Homes for sale in Chestertown
Explore homes currently listed for sale in Chestertown, New York across major real estate platforms.
Who lives in Chestertown?
Population
529
Median income
$64,438/yr
Median age
39.8 years
Owner-occupied
68.5%
College grads
27.7%
Avg commute
27.9 min
Source: U.S. Census Bureau ACS
What are homes worth in Chestertown?
Zillow home value
$392,874
Price-to-income
6.1x
Source: Zillow Research
What is it like to live in Chestertown?
Chestertown is a community of approximately 1K residents with a median age of 39.8 years.The median household income is $64,438, which represents a working-class community with solid middle-income opportunities. 27.7% of residents hold a bachelor's degree or higher, showing a mixed educational demographic.
Homeownership rates are at 68.5%, reflecting strong community stability and long-term resident commitment. The average commute time is 27.9 minutes, which makes this an excellent choice for those seeking short commutes to employment centers.Overall, Chestertown offers a balanced lifestyle with accessible home values relative to local income levels.
Which public schools serve Chestertown?
1 schools tracked · 472 students
The largest public schools serving Chestertown, NY by enrollment, drawn from the National Center for Education Statistics. School quality is a commonly cited factor in home-buying decisions — these are the campuses families in this area are most likely to encounter.
NORTH WARREN CENTRAL SCHOOL
Grades PK-12 · 472 students
Source: National Center for Education Statistics, Common Core of Data directory. Updated annually. Ratings and test scores are not currently displayed.
Which cities are near Chestertown, NY?
Want a head-to-head view? Compare Chestertown side-by-side with any other U.S. city using our market-comparison tool.
Frequently asked questions
What is the average home price in Chestertown?
The median home sale price in Chestertown is $310,000, down 7.5% from last year.
How long do homes stay on market in Chestertown?
Homes typically spend 61 days on market before going under contract.
What is the median income in Chestertown?
The median household income is $64,438 per year.
What is the Zillow home value estimate for Chestertown?
The Zillow Home Value Index (ZHVI) for Chestertown is $392,874, representing the typical home value in the area.
What is the median condo price in Chestertown?
The median condo/co-op sale price in Chestertown, NY is $310,000, compared to $279,750 for a single-family home, based on the latest Redfin data.
How much does a single-family home cost in Chestertown?
The median single-family home price in Chestertown, NY is $279,750 (about $194 per square foot).
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