Chestertown

Background Image

Chestertown, MD

Area Guide

Share Guide

Take it easy in this historic town on the river

Historic Riverside Scenic Rural Laidback Convenient Charming

Located on the western banks of the Chester River, Chestertown boasts a rich history in a scenic environment. Chestertown is surrounded by farmland, exuding a rural small-town vibe. Chestertown residents enjoy a slow-paced approach to life, with plenty of time to stroll the waterfront at Wilmer Park and peruse the many shops in the Chestertown Historic District.

A bevy of annual events bring the Chestertown community together, including the Harry Potter Festival, Jazz Festival, Tea Party Festival, Porchfest, Riverfest, National Music Festival, and Taste of Chestertown. Chestertown is also home to Washington College, the first college chartered in the newly independent United States following the Revolutionary War. Big-city amenities aren’t too far away, with larger cities like Philadelphia, Baltimore, and Washington, DC just a 90-minute drive from Chestertown.

Rent Trends

As of March 2025, the average apartment rent in Chestertown, MD is $1,304 for one bedroom, $1,457 for two bedrooms, and $1,856 for three bedrooms. Apartment rent in Chestertown has increased by 7.1% in the past year.

Property Type
Average Rent
Average Sq Ft
Apartment
$1,304/month
754 Sq Ft
See Rental Market Trends in Chestertown, MD

Transportation

47

Car-Dependent

out of 100 WalkScore® Rating

This area is considered a car-dependent area and most errands will require a car.

55

Bikeable

out of 100 BikeScore® Rating

While there’s some bike infrastructure in this area, you’ll still need a car for many errands.

Schools

H. H. Garnett Elementary

Public

Grades PK-5

347 Students

4
out of 10

Kent County Middle School

Public

Grades 6-8

399 Students

3
out of 10

Points of Interest

Top Apartments in Chestertown

Houses for Rent in Chestertown

Search Nearby Rentals

Methodology

† Our analysis of utilities, groceries, transportation, healthcare, home prices, and other goods and services is sourced from the Cost of Living Index, a respected benchmark published by the Council for Community and Economic Research (C2ER) that provides a thorough overview of living expenses across different regions.

Rent data is provided by CoStar Group’s Market Trend reports. As the industry leader in commercial real estate information, analytics, and news, CoStar conducts extensive research to produce and maintain a comprehensive database of commercial real estate information. We combine this data with public record to provide the most up-to-date rental information available.

Consumer goods, services, and home prices are sourced from the Cost of Living Index published by the Council for Community and Economic Research (C2ER). The data on this page is updated quarterly. It was last published in February 2025.