Kent County

The house is surrounded by green grass and trees, and there is a blue sky in the background.

Welcome to

Kent County is a predominantly agricultural area steeped in rich maritime history with a small-town lifestyle.

Property Listings

$14,800,000

6 bd 4 ba 6,144 Sq.Ft. Pending

22076 Napley Green Rd, Rock Hall, MD 21661

MLS®: MDKE2004702

$14,800,000

6 bd 4 ba 6,144 Sq.Ft. Pending

22076 Napley Green Rd, Rock Hall, MD 21661

MLS®: MDKE2004788

$5,900,000

6 bd 5 ba 4,214 Sq.Ft. For Sale

5135 Crosby Rd, Rock Hall, MD 21661

MLS®: MDKE2004950

$5,900,000

6 bd 5 ba 4,214 Sq.Ft. For Sale

5135 Crosby Rd, Rock Hall, MD 21661

MLS®: MDKE2004938

$5,500,000

5 bd 8 ba 9,852 Sq.Ft. Pending

23620 Lands End Rd, Chestertown, MD 21620

MLS®: MDKE2004760

$3,000,000

Cromwell Clark Rd, Chestertown, MD 21620

MLS®: MDKE2005156

Search Homes in the Area

Welcome to Kent County, Maryland

Historic charm meets waterfront tradition in a scenic Chesapeake Bay retreat.

Kent County is one of Maryland’s most picturesque and storied waterfront regions, home to the charming towns of Chestertown, Rock Hall, and Betterton. Set against the serene backdrop of the Chester River and the upper Chesapeake Bay, this town-centered community offers timeless appeal and small-town intimacy, enriched by deep-rooted traditions, colonial heritage, and a welcoming pace of life.

From its colonial architecture and brick-lined streets in Chestertown to the boating culture of Rock Hall and the beach town feel of Betterton, Kent County delivers a sense of place that’s both relaxing and culturally rich. With strong ties to the water, this area invites you to slow down, soak in the surroundings, and experience an authentic slice of the Eastern Shore lifestyle.

What to Love

A strong sense of history and preserved colonial architecture
Active waterfront culture with boating, sailing, and riverside events
Celebrated annual festivals and community traditions
Small-town atmosphere with rich cultural and culinary offerings
Scenic countryside paired with access to the Chester River and Bay

Local Lifestyle

Kent County residents enjoy a lifestyle that’s rooted in local pride, tradition, and the outdoors. The towns here are close-knit, where shopkeepers know your name and everyone turns out for community events. Whether you're sailing out of Rock Hall Harbor, attending a weekend farmer’s market in Chestertown, or relaxing on Betterton Beach, the pace of life is calm, reflective, and deeply connected to nature and history.

Founded in 1782, Washington College in Chestertown is the 10th oldest college in the United States. Its walkable, tree-lined campus blends classic brick architecture with modern academic buildings. Facilities include docks and a boathouse for the school’s sailing and rowing teams. The Miller Library, Gibson Center for the Arts, and Hodson Hall Commons serve as campus landmarks and host events open to the broader community. The college’s location within walking distance of downtown Chestertown makes it easy to explore local shops, galleries, and cafes

Dining and Shopping

Kent County may be quiet, but it’s full of exceptional, locally loved spots. In Chestertown, Evergrain Bread Company is a staple for artisan baked goods, offering fresh bread, pastries, and coffee in a cozy, historic building. Locals patronize restaurants like The Kitchen at the Imperial and Blue Bird Tavern; the former serves fantastic crab cakes, while the latter is known for hearty sandwiches, in-house soups, and frosty beer mugs.

Java Rock in Rock Hall is the kind of neighborhood café that fuels both locals and visitors, serving fresh coffee and gourmet sandwiches just a short stroll from the marina. For something truly unique, Crow Vineyards offers wine tastings and farm experiences on a family-run vineyard just outside town, showcasing the region’s agricultural excellence.

Shopping here is about supporting local artisans and makers, with everything from boutique gifts and antiques to specialty wine and food products, often tied to the area's Chesapeake heritage.

Things to Do and Entertainment

Kent County shines when it comes to annual events. The Chestertown Tea Party Festival is one of the region’s most iconic celebrations, drawing thousands each Memorial Day weekend to commemorate colonial resistance with reenactments, parades, and artisan markets. In fall, the Sultana Downrigging Weekend brings tall ships to the waterfront, with maritime-themed festivities and sailing excursions that honor the county’s seafaring roots.

Pirates and Wenches Weekend in Rock Hall is a playful, family-friendly favorite that transforms the harbor into a pirate-themed party complete with costumes, games, and local food. It’s the kind of event that perfectly captures Kent County’s mix of fun, heritage, and community spirit.

Overview for Kent County, MD

19,335 people live in Kent County, where the median age is 47.1 and the average individual income is $39,658. Data provided by the U.S. Census Bureau.

19,335

Total Population

47.1 years

Median Age

Medium

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

$39,658

Average individual Income

Around Kent County, MD

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

31

Somewhat Bikeable

Bike Score

Points of Interest

Explore popular things to do in the area, including Bespoke Chocolate, Modern Stone Age Kitchen, and Phat Daddy's BBQ.

Name	Category	Distance	Reviews	Ratings by Yelp
Visit the Bespoke Chocolate page on Yelp Search 207 S Cross St on Google Maps	Dining	2.45 miles	9 reviews	4.9/5 stars
Visit the Modern Stone Age Kitchen page on Yelp Search 236 Cannon St on Google Maps	Dining	2.45 miles	30 reviews	4.6/5 stars
Visit the Phat Daddy's BBQ page on Yelp Search 205 Spring Ave on Google Maps	Dining · $$	2.36 miles	46 reviews	4.6/5 stars
Visit the Watershed Alley page on Yelp Search 337 High St on Google Maps	Dining · $$$	2.34 miles	55 reviews	4.6/5 stars
Visit the Chester River Wine & Cheese page on Yelp Search 117 S Cross St on Google Maps	Dining · $$	2.43 miles	32 reviews	4.6/5 stars
Visit the Bookplate page on Yelp Search 112 S Cross St on Google Maps	Shopping	2.41 miles	21 reviews	4.6/5 stars
Visit the Body Mechanics Massage Studio page on Yelp Search 102 S Lynchburg St on Google Maps	Beauty	1.96 miles	3 reviews	5/5 stars
Visit the Flow Salonspa page on Yelp Search 305 High St on Google Maps	Beauty	2.4 miles	3 reviews	5/5 stars

Demographics and Employment Data for Kent County, MD

Population Households Employment

Kent County has 8,291 households, with an average household size of 2.13. Data provided by the U.S. Census Bureau. Here’s what the people living in Kent County do for work — and how long it takes them to get there. Data provided by the U.S. Census Bureau. 19,335 people call Kent County home. The population density is 69.79 and the largest age group is Data provided by the U.S. Census Bureau.

19,335

Total Population

Medium

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

47.1

Median Age

47.74 / 52.26%

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

8,291

Total Households

2.13

Average Household Size

$39,658

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

Kent County

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Kent County

Property Listings