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 $867K
Lowest Price $24
Highest Price $20M
Total Listings 273
Avg. Days On Market 86
Avg. Price/SQFT $337

Property Types (active listings)

Chestertown Homes for Sale

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New
23620 Lands End Rd, CHESTERTOWN

$5,500,000

23620 Lands End Rd, CHESTERTOWN

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

Cross Street Realtors LLC

240 Round Top Landing Rd, CHESTERTOWN

$3,750,000

↓ $245,000

240 Round Top Landing Rd, CHESTERTOWN

3 Beds 3.5 Baths 4,804 SqFt Residential MLS® # MDQA2009012

TTR Sotheby's International Realty

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

26865 Mallard Rd, CHESTERTOWN

$999,000

26865 Mallard Rd, CHESTERTOWN

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

TTR Sotheby's International Realty

230 S Water St #1, CHESTERTOWN

$995,000

230 S Water St #1, CHESTERTOWN

3 Beds 3.5 Baths 2,490 SqFt Residential MLS® # MDKE2001598

Gunther-McClary Real Estate

228 S Water St, CHESTERTOWN

$950,000

228 S Water St, CHESTERTOWN

3 Beds 3.5 Baths 0 SqFt Residential MLS® # MDKE2001612

Gunther-McClary Real Estate

Lot 3 Muirfield Dr, CHESTERTOWN

$790,000

Lot 3 Muirfield Dr, CHESTERTOWN

3 Beds 2.5 Baths 0 SqFt Residential MLS® # MDKE2004262

Gunther-McClary Real Estate

212 Landing Ln, CHESTERTOWN

$779,000

212 Landing Ln, CHESTERTOWN

3 Beds 3.5 Baths 0 SqFt Residential MLS® # MDKE2004782

Gunther-McClary Real Estate

117 N Water St #1a, CHESTERTOWN

$725,000

↓ $25,000

117 N Water St #1a, CHESTERTOWN

3 Beds 3 Baths 0 SqFt Residential MLS® # MDKE2004206

Gunther-McClary Real Estate

11040 Kylie Ln, CHESTERTOWN

$698,000

11040 Kylie Ln, CHESTERTOWN

4 Beds 3.5 Baths 3,684 SqFt Residential MLS® # MDKE2004586

Coldwell Banker Chesapeake Real Estate Company

New
317 Union Church Rd, CHESTERTOWN

$685,000

317 Union Church Rd, CHESTERTOWN

4 Beds 3.5 Baths 2,512 SqFt Residential MLS® # MDQA2012076

Clark & Co Realty, LLC

7938 Radcliffe Rd, CHESTERTOWN

$585,000

7938 Radcliffe Rd, CHESTERTOWN

5 Beds 3.5 Baths 2,408 SqFt Residential MLS® # MDKE2004638

TTR Sotheby's International Realty

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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