Chestertown housing market,
at a glance.
63 active homes·$424,900 median asking·85 median days listed
Updated September 20, 2026. Active asking prices only, not sold prices and not an appraisal. Check official sources before acting.
Chestertown market snapshot
As of September 20, 2026
63
Active homes
3 new in 7 days
$424,900
Median asking price
$85,000–$1,500,000
$279/sq ft
Median price per sq ft
1,964 sq ft typical
85 days
Median days listed
typically built 1983
What stands out today
- 49%listed over 90 days31 of 63 active homes.
- 68%single family inventory43 of 63 listings with a stated type.
- 202 daysmedian for 1 bed listingsThe longest wait of any bedroom band here.
By bedroom count
1 bed listings wait longest: a median of 202 days, against 64 for 4 bed.
Houses, condos and townhouses, 62 of 63 active homes. Whole buildings and land have no bedroom count; they are in Property mix.
| Bedrooms | For sale | Median asking | Days listed |
|---|---|---|---|
| 1 bedlow sample | 3 | $295,000 | 202 days |
| 2 bedlow sample | 5 | $375,000 | 99 days |
| 3 bed | 32 | $335,000 | 74 days |
| 4 bed | 13 | $429,900 | 64 days |
| 5+ bedlow sample | 9 | $824,900 | 114 days |
Inventory age
49% of active homes have been listed more than 90 days. This reflects today's active inventory, not a trend over time.
40%
11%
49%
- Under 60 days
- 40%
- 25 homes
- 60–90 days
- 11%
- 7 homes
- Over 90 days
- 49%
- 31 homes
Property mix
Single Family homes are 68% of what is for sale.
| Single Family$375,000 | 4368% | |
|---|---|---|
| Condo$786,900 | 1524% | |
| Townhouse$264,900 | 58% |
Compare nearby markets
Ordered by active listings, not by any view of where to buy.
BaltimoreBaltimore City
$234,900 median ask · 3,536 homes · 59 days
Ocean CityWorcester
$465,000 median ask · 523 homes · 92 days
FrederickFrederick
$489,000 median ask · 507 homes · 36 days
Silver SpringMontgomery
$535,000 median ask · 421 homes · 31 days
HagerstownWashington
$324,900 median ask · 391 homes · 46 days
Upper MarlboroPrince George's
$489,000 median ask · 365 homes · 44 days
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Active asking prices only, not sold prices and not an appraisal. Check official sources before acting.About this data
- Active asking prices only, not sold prices and not an appraisal. Check official sources before acting.
- Coverage is the areas EuKreate tracks, so this is not the whole market.
- Whether a home is under contract is not in the data we receive, so no pending count is shown.
- No trend yet: we began measuring this area on 2026-09-20, and a change needs two measurements.
- EuKreate began tracking Chestertown on September 20, 2026. Movement appears once there are enough daily readings to compare.