Property details·Chestertown, Kent County, Maryland·04-020561
112 Riverside Terrace
Chestertown, MD 21620
Kent County
04-020561
39.210513, -76.061477
County context
There's a particular kind of quiet that settles over Kent County. Perched on Maryland's Eastern Shore, bordered by the Chester River to the south and the Sassafras to the north, this is one of the smallest counties by population in Maryland — fewer than 20,000 residents spread across 70 people per square mile of farmland, waterfront, and colonial-era towns. Chestertown, the county seat, is the kind of place where George Washington actually slept, where Washington College has educated students since 1782, and where the Saturday farmers market draws more foot traffic than most of the week combined. The data portrait of Kent County is, accordingly, distinctive in ways that demand explanation.
The median age of 48.4 — well above the national median of around 38 — tells you immediately that this is retirement and second-home country. Over a quarter of Kent County's population is 65 or older, while children under 18 make up only 15.6%. That demographic inversion shapes almost everything: lower school enrollment, depressed labor force participation at 58.8%, and a housing stock that skews toward owner-occupied single-family homes (80.3%), many of them primary residences for retirees and weekend escapes for Washington D.C. and Baltimore professionals just 90 minutes away.
What's striking is the education profile alongside the income data. Nearly 38% of adults hold a bachelor's or graduate degree — a figure that would be unremarkable in a suburb but is notably high for a rural Eastern Shore county. Yet the median household income of $74,402 barely clears the national benchmark of $75,149. That gap between credentials and earnings suggests a community where professionals have chosen a lower-earning lifestyle — academics at Washington College, artists, retirees living on fixed incomes — rather than a workforce constrained by limited opportunity.
| Stat | Value | Context |
|---|---|---|
| Median Home Value | $307,100 | Slightly below national avg of $320,000 |
| Homeownership Rate | 72.1% | Well above national avg of ~65% |
| Vacancy Rate | 17.4% | Nearly 3x the typical urban benchmark |
| Rent Burden | 50.0% | Severe — renters are squeezed hard |
The homeownership story looks enviable on the surface, but Kent County harbors a quiet crisis for the 27.9% of households who rent. A median rent of $1,144 against incomes that skew lower for renters than owners produces a rent burden sitting at exactly 50% — meaning the median renting household spends half their gross income on housing. Over one in five renters (21.3%) faces severe rent burden exceeding their means significantly. In a county without major employers, significant transit infrastructure, or a dense affordable housing stock, renters — often younger workers, service industry employees, and those supporting the hospitality and agricultural sectors — are profoundly exposed.
The 17.4% vacancy rate adds another wrinkle. That's not a sign of a depressed market so much as a seasonal and second-home economy: waterfront properties sitting empty most of the year inflate the vacancy figure while simultaneously driving up values and rents for locals who need housing year-round.
What makes Kent County, Maryland unique? Kent County is one of Maryland's smallest and oldest counties, defined by its Chesapeake Bay waterfront character, colonial history, and a population skewed heavily toward retirees and second-home owners. Washington College in Chestertown anchors an educated, arts-oriented community that sits somewhat incongruously within a rural agricultural economy — creating a demographic profile unlike almost any other county its size in the Mid-Atlantic.
Is Kent County affordable to buy a home? For buyers, yes — at $307,100, median home values sit just below the national average, and with a homeownership rate of 72.1%, ownership is clearly attainable for residents with stable incomes. The price-to-income ratio of roughly 4.1x is close to the national benchmark of 4x, making ownership more accessible here than in much of coastal Maryland.
Why are renters so financially stressed in Kent County? The same waterfront desirability that makes Kent County attractive to retirees and weekend visitors compresses the rental market. With limited affordable rental inventory and no significant public transit to nearby employment centers, renters — often lower-wage workers in agriculture, hospitality, and services — pay a disproportionate share of income on housing, with the median renter household spending fully half their income on rent.
Our database includes 9,364 properties in Chestertown.
With an average price of $428,552, Chestertown offers mid-range housing options.
Buyers can expect to pay around $201 per square foot in this market.
Home prices in Chestertown are 5% higher than the Kent County average.
| Metric | Chestertown | Kent County | vs County |
|---|---|---|---|
| Average Price | $428,552 | $406,288 | +5% |
| Avg Sq Ft | 2,131 | 2,072 | +3% |
| Price/Sq Ft | $201 | $196 | +3% |
| Properties | 9,364 | 16,026 | -42% |
The average home price in Chestertown, MD is $428,552, based on analysis of 9,364 properties in our database.
Our database includes 9,364 properties in Chestertown, MD, providing comprehensive market coverage.
The average price per square foot in Chestertown, MD is $201. This is calculated from an average home price of $428,552 and average size of 2,131 square feet.
Homes in Chestertown, MD average 2,131 square feet, with an average price of $428,552.
Chestertown, MD is one of many cities in Kent County, MD with property data available. Browse other cities in the county to compare market conditions and pricing.
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