The Town FilesChestertown, Maryland
Town in Kent County · population 5,532 (2020 Census)
- Median home
- $344,000
- Household income
- $54,346
- Jan low / Jul high
- 27° / 87°
- Snow a year
- 17 in
- Tornadoes ≤10 mi since 1950
- 6
- Median age
- 32.6
Chestertown is a town of 5,532 people in Kent County, Maryland. The median home is worth $344,000, below the typical Maryland town ($412,300). It ranks more seaside character than 99% of Maryland towns, hipper than 97% of Maryland towns, better for young professionals than 90% of Maryland towns.
How Chestertown ranks
Percentile among Maryland towns with at least 500 people on The Town Files lifestyle rankings. 50 is typical for the state; 90 means better than 90% of Maryland towns.
Homes and cost of living
The median home in Chestertown is worth $344,000, below the typical Maryland town ($412,300). Homes cost about 6.3 times the median household income of $54,346, which is more affordable than 5% of Maryland towns. Median rent is $1,206 a month. 51.8% of households own their home.
| Housing | Chestertown | Typical Maryland town |
|---|---|---|
| Median home value | $344,000 | $412,300 |
| Median rent | $1,206 | $1,748 |
| Median household income | $54,346 | $108,677 |
| Home value ÷ income | 6.3× | 3.8× |
| Homeownership | 51.8% | 77.3% |
| Median year built | 1982 | 1980 |
| Seasonal / vacation homes | 2.2% | — |
Who lives in Chestertown
| People | Chestertown | Typical Maryland town |
|---|---|---|
| Median age | 32.6 | 40.2 |
| Age 65 and over | 26.1% | 16.4% |
| Under 18 | 15.8% | — |
| Bachelor's degree or higher | 53.2% | 39.4% |
| Below the poverty line | 11.6% | 7.1% |
| Veterans | 4.5% | — |
| Born outside the U.S. | 5.2% | — |
| Work from home | 14.4% | 17.4% |
| Average commute | 19.9 min | 31.4 min |
| Homes with broadband | 84.2% | 94.3% |
Weather in Chestertown
July highs average 86.6°F and January lows 27.1°F. About 46.0 inches of rain and melted snow fall a year, with 16.7 inches of snow (typical Maryland town: 15.9 in). Expect about 37 days a year at 90°F or hotter and 97 nights at or below freezing.
Tornadoes, storms and disasters
6 tornadoes have passed within 10 miles of Chestertown since 1950, compared with 18 for the typical Maryland town. 2 rated (E)F2 or stronger. The strongest, an F2, struck on March 21, 1976 about 7.7 miles from the town center. The most recent was on May 19, 2011.
Hail of 1 inch or larger has been reported within 10 miles 9 times; the largest was 1.75 inches on May 12, 2018.
Severe weather in Kent County since 1996
Kent County has been included in 21 federal disaster or emergency declarations since 1953, most often for flood, hurricane, snowstorm.
| Declared | Incident | Declaration |
|---|---|---|
| January 24, 2026 | Winter Storm | EM-3634: Severe Winter Storm |
| March 26, 2020 | Biological | DR-4491: Covid-19 Pandemic |
| March 13, 2020 | Biological | EM-3430: Covid-19 |
| March 4, 2016 | Snowstorm | DR-4261: Severe Winter Storm And Snowstorm |
| November 20, 2012 | Hurricane | DR-4091: Hurricane Sandy |
Jobs and pay in Kent County
Kent County had 7,648 jobs in 2024, paying an average of $52,881 a year. Unemployment was 2.4% in 2023; in Chestertown itself the ACS puts it at 3.8%.
Public schools in Chestertown
2 public schools with 711 students, about 11.3 students per teacher.
| School | Grades | Students | Per teacher |
|---|---|---|---|
| Kent County Middle School | 6-8 | 382 | 10.6 |
| H. H. Garnett Elementary | PK-5 | 329 | 12.2 |
Towns near Chestertown
- Centreville, MD12.2 mi · 4,727 people · home $449,900
- Bowleys Quarters, MD17.7 mi · 6,853 people · home $400,100
- Edgewood, MD18.3 mi · 25,713 people · home $242,200
- Grasonville, MD19.2 mi · 3,474 people · home $459,600
- Abingdon, MD20.0 mi · 4,826 people · home $366,200
- Joppatowne, MD20.2 mi · 13,425 people · home $342,300
- Riverside, MD20.2 mi · 7,021 people · home $246,100
- Edgemere, MD20.5 mi · 9,069 people · home $372,600
Chestertown questions
Is Chestertown, Maryland a good place to retire?
On The Town Files lifestyle rankings, Chestertown scores better for retirees than 86% of Maryland towns and quieter than 39%. 26.1% of residents are 65 or older (median age 32.6).
How much does a house cost in Chestertown?
The median owner-occupied home in Chestertown is valued at $344,000 (Census ACS 2020–2024), against a median household income of $54,346, so homes cost about 6.3 times income. Median rent is $1,206 a month.
What is the weather like in Chestertown?
July highs average 86.6°F and January lows 27.1°F (NOAA 1991–2020 normals). It gets about 46.0 inches of precipitation a year and 16.7 inches of snow.
Does Chestertown get tornadoes?
6 tornadoes have passed within 10 miles of Chestertown since 1950 (NOAA Storm Events); the strongest was a F2 on March 21, 1976. The typical Maryland town has had 18.
- U.S. Census Bureau, American Community Survey 5-year estimates (2020–2024)
- U.S. Census Bureau, 2020 Census and 2025 Gazetteer (2020 / 2025)
- NOAA NCEI U.S. Climate Normals (1991–2020)
- NOAA NCEI Storm Events Database (1950–2026)
- FEMA OpenFEMA Disaster Declarations (this product uses the FEMA OpenFEMA API but is not endorsed by FEMA) (1953–2026)
- NCES Common Core of Data (2023–24)
- BLS Quarterly Census of Employment and Wages; USDA ERS county unemployment (BLS LAUS) (2000–2024)
- The Town Files lifestyle rankings, built from federal demographic, school, crime and housing data (2025)