Chestertown, MD Housing Market

The Chestertown housing market is somewhat competitive. The median sale price of a home in Chestertown was $283K last month, up 2.9% since last year. The median sale price per square foot in Chestertown is $158, down 24.0% since last year.

Trends
Demand
Migration
Schools
Climate

Chestertown Housing Market Trends

What is the housing market like in Chestertown today?

$283K

Sale Price

+2.9%
since last year

$158

Sale $/Sq. Ft.

-24.0%
since last year

Under List Price

2.5%

Days on Market

Down Payment

—

Total Homes Sold

To compare other locations to the Chestertown and U.S. housing market, enter a city, neighborhood, state, or zip code into the search bar. Learn which home features in Chestertown add value to a home.

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How hot is the Chestertown housing market?

Chestertown is somewhat competitive. Homes sell in 51 days.

100

Somewhat Competitive

Some homes get multiple offers.
The average homes sell for about 3% below list price and go pending in around 51 days.
Hot homes
can sell for around list price and go pending in around 16 days.

Compare With Nearby Cities

Middle River

100

Somewhat Competitive

Some homes get multiple offers.
The average homes sell for about 2% below list price and go pending in around 49 days.
Hot homes
can sell for about 1% above list price and go pending in around 18 days.

Aberdeen

100

Very Competitive

Many homes get multiple offers, some with waived contingencies.
The average homes sell for about 1% below list price and go pending in around 32 days.
Hot homes
can sell for about 2% above list price and go pending in around 7 days.

See more nearby cities and neighborhoods

Chestertown Migration & Relocation Trends

No data on migration and relocation available in this area right now

Learn about migration trends in nearby cities

View houses in Chestertown that sold recently

Recently sold homes

SOLD MAR 14, 2025
$380,000 Last Sold Price
3 beds
2 baths
1,800 sq ft
409 Riverview Rd, Chestertown, MD 21620
(443) 988-0483
List Price
$387,500
Sale to List
2% under list
Days on Market
177 days
409 Riverview Rd, Chestertown, MD 21620
SOLD MAR 13, 2025
$440,000 Last Sold Price
4 beds
2.5 baths
1,848 sq ft
312 Princess Anne Dr, Chestertown, MD 21620
(410) 643-5005
List Price
$449,900
Sale to List
2% under list
Days on Market
61 days
312 Princess Anne Dr, Chestertown, MD 21620
SOLD MAR 12, 2025
$400,000 Last Sold Price
3 beds
2.5 baths
2,167 sq ft
204 Pine Cove Ln, Chestertown, MD 21620
(410) 721-0103
List Price
$395,000
Sale to List
1% over list
Days on Market
40 days
204 Pine Cove Ln, Chestertown, MD 21620
SOLD MAR 7, 2025
$685,000 Last Sold Price
4 beds
3.5 baths
2,512 sq ft
317 Union Church Rd, Chestertown, MD 21620
(410) 827-4663
List Price
$685,000
Sale to List
0% over list
Days on Market
36 days
317 Union Church Rd, Chestertown, MD 21620
SOLD MAR 6, 2025
$325,000 Last Sold Price
3 beds
1 bath
2,376 sq ft
10061 Flatland Rd, Chestertown, MD 21620
(800) 446-4267
List Price
$310,000
Sale to List
5% over list
Days on Market
38 days
10061 Flatland Rd, Chestertown, MD 21620
SOLD MAR 5, 2025
$165,300 Last Sold Price
3 beds
1 bath
1,545 sq ft
23110 Old Fairlee Rd, Chestertown, MD 21620
(410) 547-1116
List Price
$159,900
Sale to List
3% over list
Days on Market
151 days
23110 Old Fairlee Rd, Chestertown, MD 21620
SOLD MAR 3, 2025
$75,000
—beds
—baths
—sq ft
Calvert St, Chestertown, MD 21620
List Price
—
Sale to List
—
Days on Market
—
Calvert St, Chestertown, MD 21620
SOLD FEB 28, 2025
$375,000 Last Sold Price
—beds
—baths
—sq ft
224 Spring Rd, Millington, MD 21651
(240) 913-9339
List Price
$409,000
Sale to List
8% under list
Days on Market
203 days
224 Spring Rd, Millington, MD 21651
See all recently sold homes in Chestertown.
See listings

Schools in Chestertown

Learn about schools in the Chestertown area

Elementary
Middle
High

GreatSchools Rating

3/10

H. H. Garnett Elementary School

Public • PreK-5

343

Students

8 reviews

School data provided by GreatSchools. School service boundaries are intended to be used as reference only. To verify enrollment eligibility for a property, contact the school directly.

Climate's impact on Chestertown housing

Learn about natural hazards and environmental risks, such as floods, fires, wind, and heat that could impact homes in Chestertown.

Wind Factor - Major

94% of properties are at major risk of a severe wind event over the next 30 years

Heat Factor - Severe

100% of properties are at severe risk of heat over the next 30 years

Provided by First Street Foundation

More real estate resources for Chestertown

New Listings in Chestertown

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