Chestertown, MD Housing Market

Homes for sale

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

2.6%

Days on Market

43.5

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 43.5 days.

100

Somewhat Competitive

Some homes get multiple offers.
The average homes sell for about 3% below list price and go pending in around 44 days.
Hot homes
can sell for around list price and go pending in around 15 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 50 days.
Hot homes
can sell for about 1% above list price and go pending in around 21 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 29 days.
Hot homes
can sell for about 1% above list price and go pending in around 6 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 FEB 28, 2025
$355,675 Last Sold Price
3 beds
2 baths
1,872 sq ft
10724 Foreston Rd, Chestertown, MD 21620
(410) 778-0330
List Price
$337,000
Sale to List
6% over list
Days on Market
35 days
10724 Foreston Rd, 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
SOLD FEB 28, 2025
$110,000 Last Sold Price
—beds
1 bath
759 sq ft
204 Spring Rd, Millington, MD 21651
(410) 643-2244
List Price
$165,000
Sale to List
33% under list
Days on Market
114 days
204 Spring Rd, Millington, MD 21651
SOLD FEB 28, 2025
$20,000 Last Sold Price
—beds
—baths
—sq ft
Par 113 Spring Rd, Millington, MD 21651
(410) 643-2244
List Price
$50,000
Sale to List
60% under list
Days on Market
114 days
Par 113 Spring Rd, Millington, MD 21651
SOLD FEB 27, 2025
$325,000 Last Sold Price
3 beds
2 baths
2,460 sq ft
117 Primrose Road Primrose Road Rd, Chestertown, MD 21620
(410) 778-2610
List Price
$385,000
Sale to List
16% under list
Days on Market
157 days
117 Primrose Road Primrose Road Rd, Chestertown, MD 21620
SOLD FEB 27, 2025
$305,000 Last Sold Price
3 beds
1 bath
1,028 sq ft
116 Fairview Dr, Chestertown, MD 21620
(410) 778-3779
List Price
$299,900
Sale to List
2% over list
Days on Market
47 days
116 Fairview Dr, Chestertown, MD 21620
SOLD FEB 19, 2025
$283,000 Last Sold Price
3 beds
3.5 baths
1,840 sq ft
104 Oak Leaf Dr, Chestertown, MD 21620
(302) 504-6147
List Price
$289,000
Sale to List
2% under list
Days on Market
116 days
104 Oak Leaf Dr, Chestertown, MD 21620
SOLD FEB 6, 2025
$389,900 Last Sold Price
3 beds
2 baths
1,344 sq ft
109 Grant Ct, Chestertown, MD 21620
(410) 643-4663
List Price
$389,900
Sale to List
0% over list
Days on Market
71 days
109 Grant Ct, Chestertown, MD 21620
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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