Chestertown

Chestertown is the county seat of Kent County and has a population of about 5,252. Located about 90-minutes from Washington, D.C. and Philadelphia, Chestertown is a convenient location for year round living or second homes.

Chestertown Real Estate Statistics

Average Price $759K
Lowest Price $1.3K
Highest Price $8M
Total Listings 298
Avg. Days On Market 85
Avg. Price/SQFT $331

Property Types (active listings)

Chestertown Homes for Sale

Sort by:
7989 Quaker Neck Rd, CHESTERTOWN

$2,500,000

↓ $250,000

7989 Quaker Neck Rd, CHESTERTOWN

5 Beds 4.5 Baths 4,305 SqFt Residential MLS® # MDKE2005590
Little Harbor Way #1, CHESTERTOWN

$1,800,000

↑ $341,000

Little Harbor Way #1, CHESTERTOWN

4 Beds 3.5 Baths 3,540 SqFt Residential MLS® # MDKE2004992

Gunther-McClary Real Estate

Little Harbor Way #1, CHESTERTOWN

$1,459,000

Little Harbor Way #1, CHESTERTOWN

3 Beds 2.5 Baths 2,231 SqFt Residential MLS® # MDKE2005768

Gunther-McClary Real Estate

105 High St, CHESTERTOWN

$1,395,500

105 High St, CHESTERTOWN

5 Beds 4.5 Baths 3,243 SqFt Residential MLS® # MDKE2005890
#25 Landing Ln, CHESTERTOWN

$1,099,900

#25 Landing Ln, CHESTERTOWN

4 Beds 3.5 Baths 2,784 SqFt Residential MLS® # MDKE2005954

Gunther-McClary Real Estate

228 S Water St, CHESTERTOWN

$878,000

228 S Water St, CHESTERTOWN

3 Beds 3.5 Baths 2,310 SqFt Residential MLS® # MDKE2005812

Gunther-McClary Real Estate

104 Little Harbor Way, CHESTERTOWN

$849,900

104 Little Harbor Way, CHESTERTOWN

3 Beds 2.5 Baths 1,980 SqFt Residential MLS® # MDKE2005894

Gunther-McClary Real Estate

102 Little Harbor Way, CHESTERTOWN

$839,500

102 Little Harbor Way, CHESTERTOWN

3 Beds 2.5 Baths 1,964 SqFt Residential MLS® # MDKE2005950

Gunther-McClary Real Estate

104 Landing Ln, CHESTERTOWN

$813,900

104 Landing Ln, CHESTERTOWN

3 Beds 3.5 Baths 2,192 SqFt Residential MLS® # MDKE2005952

Gunther-McClary Real Estate

106 Landing Ln, CHESTERTOWN

$799,900

106 Landing Ln, CHESTERTOWN

3 Beds 3.5 Baths 2,092 SqFt Residential MLS® # MDKE2005892

Gunther-McClary Real Estate

#35 Landing Ln, CHESTERTOWN

$786,900

#35 Landing Ln, CHESTERTOWN

3 Beds 2.5 Baths 1,964 SqFt Residential MLS® # MDKE2005956

Gunther-McClary Real Estate

#37 Landing Ln, CHESTERTOWN

$765,900

#37 Landing Ln, CHESTERTOWN

3 Beds 2.5 Baths 1,964 SqFt Residential MLS® # MDKE2005960

Gunther-McClary Real Estate

CHESTERTOWN INFORMATION

Chestertown dates back to 1706 when it served as a port of entry for colonial settlers arriving to Maryland.  It was a prosperous trading and shipbuilding center.  It's shipbuilding past has been revived by the Schooner Sultana Project.  The Sultana is a replica of a traditional 18th century schooner.  It was constructed locally by a non-profit organization, and serves as a floating classroom.  Children and adults enjoy hands on educational experiences that focus on history and the study of the natural environmentChestertown Memorial Day Weekend is a big event as Chestertown kicks off each summer with the Chestertown Tea Party Festival - a weekend of fun for the whole family including a tea toss reenactment in the Chester River on the Sultana, a raft race, re-enactor street performances, colonial crafts, strolling musicians, local fare, and 5k & 10 mile run as well as other activities.

The annual Chestertown Historic House Tour is held in September.  Peek in and visit many of the area's historic homes owned by wealthy merchants in the 18th and 19th centuries.  Chestertown is also home to Washington College - the tenth oldest college in the United States.  The college was founded in 1782 with the help of George Washington who gave his name and 50 guineas to the college.  Washington served as a trustee and received an honorary degree. For more information about local activities and events, use this link Town of Chestertown or visit the Visitor Center located at 122 North Cross Street, Chestertown.  

For more information about the Chestertown area or real estate properties,
please feel free to call me at: (443) 480-1181 or send an email using the form below. Thank you - Richard.

Provide a valid email address.
Newsletter consent