Chestertown, MD
City market trends and history
Public Record
Median Sale Price
$397.5K
12-Month Sales
27
+9.1%
1-Year Appreciation
+9.1%
Properties Tracked
2,227
Median Sale Price History
Top Neighborhoods
| Name | Median |
|---|
Top Neighborhoods by Activity
| Neighborhood | Sales 12mo | Median |
|---|
Top ZIP Codes
| ZIP | Sales 12mo | Median |
|---|
Recent Sales
| Date | Address | Price |
|---|---|---|
| May 4, 2026 | Pine Tree Rd | $480K |
| Apr 21, 2026 | E Step Rd | $365K |
| Jan 21, 2026 | Cannon St | $800K |
| Dec 11, 2025 | Birch Run Rd | $475K |
| Nov 13, 2025 | 10165 JOHN CARVILL RD | $525K |
| Nov 12, 2025 | McGinnes Rd | $354.9K |
| Oct 8, 2025 | Parsons Rd | $120K |
| Oct 6, 2025 | Barroll Dr | $438K |
| Sep 30, 2025 | Barroll Dr | $438K |
| Sep 24, 2025 | Scheeler Rd | $250K |
| Aug 28, 2025 | 21363 INDIANA AVE | $280K |
| Aug 28, 2025 | Longfellow Dr | $180K |
| Aug 25, 2025 | Pomona Rd | $690K |
| Aug 1, 2025 | Hyala Ct | $359K |
| Jul 29, 2025 | 22153 1ST POINT RD | $1.06M |
| Jul 28, 2025 | Devon Dr | $485K |
| Jul 22, 2025 | Cannon St | $190.5K |
| Jun 26, 2025 | 9050 POINT LN | $745K |
| Jun 26, 2025 | Dutchess Rd | $312K |
| Jun 13, 2025 | Devon Dr | $525K |
4-Quarter Forecast
Linear projection from past trendQuarterly trend
+3.8%
Implied 1-yr
+15.2%
2026 Q3
$420K
2026 Q4
$432.8K
Median Price — History + Forecast
Property type mix
Share by property type
Year-built distribution
Properties by build era
Map
Recent top sales — most expensive
| Address | Sale date | Sale price |
|---|---|---|
| Fairgale Farm Ln | Mar 1, 2023 | $2,000,000 |
| Round Top Creek Ln | May 12, 2023 | $1,950,000 |
| 10108 3RD POINT RD | Jun 29, 2023 | $1,895,000 |
| Silver Heel Dr | Aug 1, 2022 | $1,860,000 |
| River Rd | Dec 28, 2021 | $1,810,000 |
| East Fork Dr | Apr 4, 2024 | $1,770,000 |
| 9545 CHANTILLY FARM LN | Jun 5, 2024 | $1,725,000 |
| S Water St | Mar 16, 2022 | $1,700,000 |
| 210 TRUSLOW FARM LN | Jun 24, 2024 | $1,500,000 |
| Quaker Neck Rd | Jun 13, 2022 | $1,500,000 |
How Chestertown compares
| Metric | Chestertown | Maryland avg | US avg |
|---|---|---|---|
| Median price | $397.5K | $514.7K | $535.4K |
| 1-year change | +9.1% | +3.1% | -5.4% |
| Sales (12mo) | 27 | 4,940 | — |
| Median sqft | — | — | — |
Other cities in Maryland
How Chestertown ranks in Maryland
1-year appreciation
#85 of 416
Median price
#143 of 416
Frequently asked about Chestertown
What is the median sale price in Chestertown, MD?
The median sale price in Chestertown over the last 12 months is $397.5K, based on 27 transactions.
How fast are home prices appreciating in Chestertown?
Chestertown home prices have changed +9.1% year-over-year on a median basis.
How many sales happen each year in Chestertown?
Roughly 27 home sales were recorded in Chestertown over the trailing 12 months.
What types of properties are most common in Chestertown?
single_family is the most common property type tracked in Chestertown.
When were most homes in Chestertown built?
Most homes in Chestertown were built in the Pre-1950 era.