Chestertown Historic District · Photo: Acroterion · CC BY-SA 4.074 homes sold in Chestertown in the last year, at a typical $361K
Almost every sale is a house. Below: what each kind of home sells for, the best months to buy, how hard you’ll have to bid, and a shortcut to every site where Chestertown homes are listed.
Every place Chestertown homes are listed, in one stop
We don’t copy listings: the agents’ sites have the photos and the latest price changes. Set what you want once and we open each site already filtered to Chestertown.
For sale
Rent
New, land & open houses
Links open the listing sites; TownRatings isn’t paid for them and doesn’t rank one above another. Rentals and government-owned homes come from sources outside the MLS.
Houses are 0% of Chestertown’s sales, at a typical — (year to May 2026)
74 homes sold in the year to September 2026.
About as many homes sell as usual, at 1.6 times the 2016 price
74 sales in the last year, against 160 in 2021 and a low of 44 in 2012. The typical sale went from $225K in 2016 to $361K.
Source: Redfin Data Center, MLS sales; from June 2026 each month is a 3-month rolling window, its counts divided by 3. Typical price and $/sq ft are the monthly medians, weighted by sales. Redfin stopped publishing towns’ figures by property type after May 2026, so houses and condos are shown for the year to then.
Bidding wars in Chestertown are more common than before the pandemic, with about as many homes for sale
We read every month of Chestertown’s home sales since 2012 so you don’t have to. Each figure covers 12 months, because a single month in a town is too few sales to mean much. Latest: the year to September 2026, 74 sales.
If you’re buying in Chestertown
- Shop in May. It brings about 12 new listings a month, close to the busiest month, with fewer bidding wars (21% over asking).
- Offer under asking. Buyers paid 97.7% of the list price on average; 16% paid over.
- You’ll usually have time. Only 34% of homes go under contract within two weeks; the typical one takes 70 days.
Spring brings both the most homes and the most bidding wars
May has the most new listings (about 12 a month), but April is the most competitive: 23% of April sales close over asking. January has the least competition (10%) but only about 7 new listings.
Averages for each calendar month, 2015 on.
Calmer than the 2021 frenzy, and calmer than Maryland
| Chestertown now | 2017–19 | 2021 peak | MD now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 16% | 8% | 27% | 32% |
| Gone within two weeksShare of homes under contract within 14 days | 34% | 14% | 50% | 40% |
| Price paid vs. askingAverage sale price ÷ list price | 97.7% | 94.1% | 98.6% | 99.7% |
| Days to sellMedian days from listing to contract | 70 | 101 | 49 | 46 |
38 homes for sale on a typical day
That’s 2.2 times the 2022 low (17), 13% fewer than in 2017–19 and well under 2012’s 71.
Chestertown ranks 182nd of 193 busy Maryland markets for bidding wars
Share of sales over asking in the last year, among towns with 60 or more sales. Chestertown is one of the state’s calmer markets.
Source: Redfin Data Center, city figures, January 2012 to September 2026 (MLS sales, not seasonally adjusted; from June 2026 each month is a 3-month rolling window, its counts divided by 3). Ratios are weighted by homes sold; price cuts by homes for sale.
Owning the typical Chestertown home costs about $2,230 a month
Price: Chestertown’s typical sale, last 12 months. Property tax at Chestertown’s 1.2% (median bill ÷ median value, Census ACS); insurance at 0.35% of price a year. Before PMI, HOA dues, upkeep and the tax deduction. Whether Chestertown is affordable on local pay is on Cost of living.
Six things worth knowing
New listings in May
The month with the most choice. February has the fewest, about 7.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $361K home, about $4,160 a year.
Taxes vs. neighborsSchools
The schools grade for Chestertown, from test results, graduation and how much students grow.
Schools in ChestertownTypical commute
The average one-way trip to work for people who live in Chestertown.
Work & commuteCheck the flood map
Flood insurance isn’t in a standard policy, and lenders require it in FEMA flood zones. Check the address before you make an offer.
Natural hazardsLook up any property
Assessed value, lot size and every past sale of a home you’re eyeing are public, at the town or county assessor and the registry of deeds.
Edgewood and Perryman sell for less a square foot
The busier markets within 25 miles of Chestertown, by what sold. Prices, taxes and how far a paycheck goes next door are on Cost of living.
| Sold | Typical sale | $/sq ft | Over asking | Days to sell | |
|---|---|---|---|---|---|
| Edgewood | 233 | $270K | $168 | 36% | 38 |
| Bowleys Quarters | 76 | $389K | $220 | 36% | 28 |
| Chestertown | 74 | $361K | $206 | 16% | 70 |
| Centreville | 74 | $474K | $216 | 17% | 73 |
| Perryman | 43 | $268K | $152 | 28% | 92 |
| Rock Hall | 31 | $385K | $253 | 14% | 69 |
| Kingstown | 27 | $378K | $221 | 27% | 53 |
Redfin Data Center, October 2025 to September 2026. Towns with fewer than 20 sales are left out, and Redfin doesn’t report every town separately.
Post your home to Chestertown, free
Selling it yourself, renting out an apartment or looking for a roommate? Post it to Chestertown. People who follow the town see it, and so do people comparing Chestertown with their own town. No commission, no listing fee.
Questions about buying a home in Chestertown
What do homes sell for in Chestertown, MD?
74 homes sold in the year to September 2026 at a typical $361K, $206 a square foot.
Is Chestertown a buyer’s or seller’s market?
A balanced market: 37 homes were for sale in September 2026 and 7 sold, about 4.8 months of supply. Buyers paid 97.7% of asking on average.
When is the best time to buy in Chestertown?
May brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Chestertown?
About 1.2% of a home’s value a year. On a $361K home that’s near $4,160.
Where can I see homes for sale in Chestertown?
Zillow, Redfin, Realtor.com and Homes.com all carry Chestertown’s MLS listings; the search links above open each one filtered to Chestertown.
Sales, prices, days on market and listings: Redfin Data Center (MLS, monthly, not seasonally adjusted; from June 2026 each month is a 3-month rolling window, its counts divided by 3). Property tax rate: Census American Community Survey. Two-bedroom rent: HUD Fair Market Rent. Typical home value: Zillow Home Value Index. Schools grade: TownRatings (how grades work).