Waterfront homes and docks below a distant city skyline, with autumn trees and mountains on the horizon.

Chestertown Real Estate

With a strong sense of community and a variety of events.

PROPERTY LISTINGS

Aerial view of a house amid expansive green fields, a curving driveway, and wooded land.
For Sale
MLS® MDKE2007006

$38,200,000

8184 ROCK HALL ROAD, CHESTERTOWN, MD 21620
4 Beds 2 Baths 2,330 Sq.Ft.
Country road running beside a cultivated field and tree line near Chestertown.
Pending
MLS® MDKE2005156

$3,000,000

CROMWELL CLARK ROAD, CHESTERTOWN, MD 21620
Waterfront home among trees with a private dock extending into the river.
For Sale
MLS® MDKE2007098

$2,895,000

6324 QUAKER NECK ROAD, CHESTERTOWN, MD 21620
5 Beds 3.5 Baths 5,938 Sq.Ft.
Downtown storefront building with four dormer windows and River Arts signs above the entrance.
For Sale
MLS® MDKE2006810

$2,300,000

200 HIGH STREET, CHESTERTOWN, MD 21620
6,918 Sq.Ft.
Three-story home with white-railed balconies, a spiral staircase, and landscaped grounds.
For Sale
MLS® MDKE2007154

$1,800,000

LITTLE HARBOR WAY Unit: 1, CHESTERTOWN, MD 21620
4 Beds 3.5 Baths 3,540 Sq.Ft.
Gray house with dark shutters and a columned porch beside a brick sidewalk.
For Sale
MLS® MDKE2006158

$1,600,000

117 WATER STREET N 1A, 1B, 2A, & 2B, CHESTERTOWN, MD 21620
7 Beds 5 Baths 5,400 Sq.Ft.
Brick home with green shutters and a red-roofed porch behind a broad lawn.
For Sale
MLS® MDKE2006596

$1,495,000

8796 MARYLAND PARKWAY, CHESTERTOWN, MD 21620
9 Beds 6.5 Baths 4,776 Sq.Ft.
Red-and-brown house with a covered porch, landscaped lawn, and curved gravel driveway.
For Sale
MLS® MDKE2006502

$1,375,000

22470 FAIRGALE FARM LANE, CHESTERTOWN, MD 21620
4 Beds 5 Baths 4,257 Sq.Ft.
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Welcome to Chestertown Real Estate

Located in the heart of Kent County, Maryland, USA. Known for its picturesque streets, historic homes, and vibrant community, Chestertown offers a unique blend of small-town charm and modern amenities.
 
Chestertown is a place where history comes alive, with its well-preserved colonial architecture and rich maritime heritage. Residents and visitors alike can enjoy strolling along the brick sidewalks, exploring local shops and art galleries, or dining at one of the many cozy cafes and restaurants.
 
Nature enthusiasts will appreciate Chestertown's proximity to the scenic Chester River, where outdoor activities such as kayaking, fishing, and birdwatching abound. The nearby Wilmer Park provides a peaceful retreat for picnicking and enjoying the waterfront views.
 
Families will find top-rated schools in the area, making Chestertown an ideal place to raise children. With a strong sense of community and a variety of events and festivals throughout the year, there is always something to do and explore in this vibrant city.
 
Whether you are looking for a historic home with character or a modern property with all the amenities, Chestertown has something to offer everyone. Come and discover the beauty and warmth of Chestertown—a place you'll be proud to call home.

Overview for Chestertown Real Estate, MD

13,533 people live in Chestertown Real Estate, where the median age is 42.9 and the average individual income is $43,887. Data provided by the U.S. Census Bureau.

13,533

Total Population

42.9 years

Median Age

Low

Population Density Population Density This is the number of people per square mile in a neighborhood.

$43,887

Average individual Income

Around Chestertown Real Estate, MD

There's plenty to do around Chestertown Real Estate, including shopping, dining, nightlife, parks, and more. Data provided by Walk Score and Yelp.

1
Car-Dependent
Walking Score
45
Somewhat Bikeable
Bike Score

Points of Interest

Explore popular things to do in the area, including Royal Farms, Subway, and Cafe Sado.

Name Category Distance Reviews
Ratings by Yelp
Dining 0.99 miles 1 review 1/5 stars
Subway Logo
Dining · $ 1.01 miles 6 reviews 2.5/5 stars
Cafe Sado Logo
Dining · $$ 1.01 miles 75 reviews 3.4/5 stars
Papa Smurfs BBQ Food Truck Logo
Dining 1.02 miles 4 reviews 4/5 stars
Dining 1.02 miles 0 reviews 0/5 stars
Dining 1.09 miles 0 reviews 0/5 stars

Demographics and Employment Data for Chestertown Real Estate, MD

Population Households Employment

Chestertown Real Estate has 5,674 households, with an average household size of 2.12. Data provided by the U.S. Census Bureau. Here’s what the people living in Chestertown Real Estate do for work — and how long it takes them to get there. Data provided by the U.S. Census Bureau. 13,533 people call Chestertown Real Estate home. The population density is 114 and the largest age group is Data provided by the U.S. Census Bureau.

13,533

Total Population

Low

Population Density Population Density This is the number of people per square mile in a neighborhood.

42.9 years

Median Age

49 / 51%

Men vs Women

Population by Age Group

0-9:

0-9 Years

10-17:

10-17 Years

18-24:

18-24 Years

25-64:

25-64 Years

65-74:

65-74 Years

75+:

75+ Years

Education Level

  • Less Than 9th Grade
  • High School Degree
  • Associate Degree
  • Bachelor Degree
  • Graduate Degree
5,674

Total Households

2.12

Average Household Size

$43,887

Average individual Income

Households with Children

With Children:

Without Children:

Marital Status

Married
Single
Divorced
Separated

Blue vs White Collar Workers

Blue Collar:

White Collar:

Commute Time

0 to 14 Minutes
15 to 29 Minutes
30 to 59 Minutes
60+ Minutes

Schools in Chestertown Real Estate, MD

All ()
Primary Schools ()
Middle Schools ()
High Schools ()
Mixed Schools ()
The following schools are within or nearby Chestertown Real Estate. The rating and statistics can serve as a starting point to make baseline comparisons on the right schools for your family. Data provided by the U.S. Census Bureau.
Type
Name
Category
Grades
School rating

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WORK WITH JIMMY

Jimmy Rupert is a successful Maryland real estate agent and has helped hundreds of buyers and sellers turn their dreams into reality. Jimmy is committed to guiding you every step of the way-whether you’re buying or selling. Whatever your needs, he has you covered.

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CELL PHONE
(443) 618-5917

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8221 Ritchie Highway Ste 101 Pasadena, MD 21122