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City / Town Overview

Chestertown, MD

Aggregate real estate market report across all ZIPs in scope
Balanced Market
January 2026  ·  Source: Realtor.com

Market Overview

Active Listings
67
⇧ 31.4% vs 51 last year
Pending
20
30% pending ratio
Median Price
$487,450
⇧ 23.9% vs $393,425 last year
Average Price
$609,662
⇧ 3.3% vs $590,117 last year
Days on Market
66
⇩ 13.2% vs 76 days last year

Market Analysis

Data as of January 2026. Source: Realtor.com.

The Chestertown, MD real estate market currently shows 67 active listings, with 20 pending sales. Homes are averaging 66 days on the market before going under contract.

Inventory has increased compared to last year, with 16 more homes available — giving buyers more choice.

Homes are selling faster, averaging 66 days on market compared to 76 days last year.

The median listing price has risen 23.9% year-over-year, from $393,425 to $487,450.

Whether you are buying or selling in Chestertown, MD, SELL123.com can help you save significantly on commission — typically 2% compared to traditional 5% broker fees. Call (240) SELL-123 for a free consultation.

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Included Areas

Chestertown: 21620, 21690

Market Context

ZIP coverage: 2  ·  Population: 13,636  ·  Median household income: $69,842

Typical home value: $304,404  ·  Homeownership rate: 69.2%

12-Month Trends

Historical Trend Charts

Median Price
Average Price
Days on Market
Total Listings
Pending Listings
Active Listings
New Listings