A Colonial Town with a Storied Past

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 $1M
Lowest Price $28
Highest Price $11.5M
Total Listings 423
Avg. Days On Market 70
Avg. Price/SQFT $384

Property Types (active listings)

Chestertown Homes for Sale

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23620 Lands End Rd, CHESTERTOWN

$4,850,000

↓ $650,000

23620 Lands End Rd, CHESTERTOWN

5 Beds 7 Baths 9,852 SqFt Residential MLS® # MDKE2004760

Cross Street Realtors LLC

7989 Quaker Neck Rd, CHESTERTOWN

$2,750,000

7989 Quaker Neck Rd, CHESTERTOWN

5 Beds 4.5 Baths 4,305 SqFt Residential MLS® # MDKE2005590

Coldwell Banker Chesapeake Real Estate Company

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

7961 Quaker Neck Rd, CHESTERTOWN

$1,550,000

↑ $55,000

7961 Quaker Neck Rd, CHESTERTOWN

5 Beds 4 Baths 4,167 SqFt Residential MLS® # MDKE2005090

Compass

105 High St, CHESTERTOWN

$1,395,500

↑ $500

105 High St, CHESTERTOWN

5 Beds 4.5 Baths 3,243 SqFt Residential MLS® # MDKE2005002

Coldwell Banker Chesapeake Real Estate Company

New
119 High St, CHESTERTOWN

$1,250,000

119 High St, CHESTERTOWN

5 Beds 4.5 Baths 4,409 SqFt Residential MLS® # MDKE2005728

Cross Street Realtors LLC

300 Hickory Ln, CHESTERTOWN

$1,198,000

↓ $99,000

300 Hickory Ln, CHESTERTOWN

5 Beds 3.5 Baths 3,640 SqFt Residential MLS® # MDQA2013388

Gunther-McClary Real Estate

23393 Cacaway Farm Ln, CHESTERTOWN

$1,195,000

↓ $55,000

23393 Cacaway Farm Ln, CHESTERTOWN

3 Beds 3.5 Baths 4,446 SqFt Residential MLS® # MDKE2004002

Gunther-McClary Real Estate

226 S Water St, CHESTERTOWN

$998,000

226 S Water St, CHESTERTOWN

3 Beds 3.5 Baths 0 SqFt Residential MLS® # MDKE2004940

Gunther-McClary Real Estate

New
492 Pear Tree Point Rd, CHESTERTOWN

$920,000

492 Pear Tree Point Rd, CHESTERTOWN

3 Beds 2 Baths 2,632 SqFt Residential MLS® # MDQA2015126

Coldwell Banker Chesapeake Real Estate Company

New
10050 Forrest Ln, CHESTERTOWN

$899,000

10050 Forrest Ln, CHESTERTOWN

4 Beds 2 Baths 1,820 SqFt Residential MLS® # MDKE2005792

Coldwell Banker Chesapeake Real Estate Company

10761 Kasota Rd, CHESTERTOWN

$895,000

10761 Kasota Rd, CHESTERTOWN

3 Beds 3 Baths 2,582 SqFt Residential MLS® # MDKE2005698

Coldwell Banker Chesapeake Real Estate Company

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.

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