Chestertown Real Estate Statistics
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.
Property Types (active listings)
Average Price: $656,617
Total Listings: 101
Avg. Days On Market: 183
Avg. Price/SQFT: $221
Highest Price: $6,500,000
Lowest Price: $19,500
Avg. Property Age: 119 YEARS
Basic Statistics (active listings)

Chestertown Homes for Sale

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
6798 Broad Neck Rd, CHESTERTOWN
  • Farm
  • 5 Beds
  • 5.5 Baths
  • 11,840 SqFt

6798 Broad Neck Rd, CHESTERTOWN

$6,500,000
6798 Broad Neck Rd, CHESTERTOWN
  • Residential
  • 5 Beds
  • 5.5 Baths
  • 11,840 SqFt

6798 Broad Neck Rd, CHESTERTOWN

$6,500,000
4746 Cliffs City Rd, CHESTERTOWN
  • Residential
  • 5 Beds
  • 4 Baths
  • 5,174 SqFt

4746 Cliffs City Rd, CHESTERTOWN

$3,400,000
23791 Ricauds Branch Rd, CHESTERTOWN
  • Farm
  • 3 Beds
  • 2.5 Baths
  • 3,248 SqFt

23791 Ricauds Branch Rd, CHESTERTOWN

$2,925,000
24091 Providence Plantation Ln, CHESTERTOWN
  • Farm
  • 5 Beds
  • 5.5 Baths
  • 5,190 SqFt

24091 Providence Plantation Ln, CHESTERTOWN

$2,650,000 ↓ $145,000
24091 Providence Plantation Ln, CHESTERTOWN
  • Residential
  • 5 Beds
  • 5.5 Baths
  • 5,250 SqFt

24091 Providence Plantation Ln, CHESTERTOWN

$2,650,000 ↓ $145,000
8744 S Bayview Dr, CHESTERTOWN
  • Residential
  • 5 Beds
  • 5.5 Baths
  • 6,105 SqFt

8744 S Bayview Dr, CHESTERTOWN

$1,950,000 ↓ $449,000
7250 Pentridge Ln, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 0 SqFt

7250 Pentridge Ln, CHESTERTOWN

$1,650,000 ↓ $200,000
7250 Pentridge Ln, CHESTERTOWN
  • Farm
  • 4 Beds
  • 2.5 Baths
  • 0 SqFt

7250 Pentridge Ln, CHESTERTOWN

$1,650,000
19 Byford Ct, CHESTERTOWN
  • Residential
  • 5 Beds
  • 6 Baths
  • 7,505 SqFt

19 Byford Ct, CHESTERTOWN

$1,195,000
5886 Quaker Neck Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 3 Baths
  • 2,524 SqFt

5886 Quaker Neck Rd, CHESTERTOWN

$1,095,000 ↓ $90,000
102 Cannon St, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 2,028 SqFt

102 Cannon St, CHESTERTOWN

$995,000

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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Bright MLS Logo© 2020 BRIGHT, All Rights Reserved. Information deemed reliable but not guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Coldwell Banker Chesapeake Real Estate Company participates, and is provided by BRIGHT through a licensing agreement. Real estate listings held by brokerage firms other than Coldwell Banker Chesapeake Real Estate Company are marked with the IDX logo and detailed information about each listing includes the name of the listing broker.The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller.

Listing information last updated on July 6th, 2020 at 4:06am EDT.