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 $24
Highest Price $20M
Total Listings 431
Avg. Days On Market 71
Avg. Price/SQFT $393

Property Types (active listings)

Chestertown Homes for Sale

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21082 Wyoming Ave, CHESTERTOWN

$1,550,000

↓ $249,000

21082 Wyoming Ave, CHESTERTOWN

3 Beds 3.5 Baths 2,699 SqFt Residential MLS® # MDKE2005016

Doug Ashley Realtors, LLC

26875 Mallard Rd, CHESTERTOWN

$1,495,000

26875 Mallard Rd, CHESTERTOWN

3 Beds 3.5 Baths 3,789 SqFt Residential MLS® # MDKE2005186

Gunther-McClary Real Estate

Little Harbor Way #1, CHESTERTOWN

$1,459,000

Little Harbor Way #1, CHESTERTOWN

3 Beds 2.5 Baths 2,315 SqFt Residential MLS® # MDKE2004992

Gunther-McClary Real Estate

23393 Cacaway Farm Ln, CHESTERTOWN

$1,450,000

23393 Cacaway Farm Ln, CHESTERTOWN

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

Gunther-McClary Real Estate

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
209 N Water St, CHESTERTOWN

$1,350,000

209 N Water St, CHESTERTOWN

5 Beds 3.5 Baths 2,909 SqFt Residential MLS® # MDKE2005212

Cross Street Realtors LLC

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

26865 Mallard Rd, CHESTERTOWN

$950,000

↓ $49,000

26865 Mallard Rd, CHESTERTOWN

4 Beds 3 Baths 3,355 SqFt Residential MLS® # MDKE2004550

TTR Sotheby's International Realty

228 S Water St, CHESTERTOWN

$898,000

↓ $52,000

228 S Water St, CHESTERTOWN

3 Beds 3.5 Baths 0 SqFt Residential MLS® # MDKE2001612

Gunther-McClary Real Estate

26889 Morgnec Rd, CHESTERTOWN

$865,000

26889 Morgnec Rd, CHESTERTOWN

2 Beds 2 Baths 1,966 SqFt Residential MLS® # MDKE2005060

Coldwell Banker Chesapeake Real Estate Company

24576 Langford Rd, CHESTERTOWN

$845,000

↓ $40,000

24576 Langford Rd, CHESTERTOWN

3 Beds 2.5 Baths 4,023 SqFt Residential MLS® # MDKE2004906

Maryland Heritage Properties

New
211 David Dr, CHESTERTOWN

$795,000

211 David Dr, CHESTERTOWN

4 Beds 4 Baths 4,401 SqFt Residential MLS® # MDKE2005038

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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