Chestertown

Chestertown Real Estate Listings
6270 Broad Neck Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 3,360 SqFt

6270 Broad Neck Rd, CHESTERTOWN

$10,000,000
4746 Cliffs City Rd, CHESTERTOWN
  • Residential
  • 5 Beds
  • 4 Baths
  • 5,174 SqFt

4746 Cliffs City Rd, CHESTERTOWN

$3,400,000
5750 Honest Point Ln, CHESTERTOWN
  • Residential
  • 4 Beds
  • 4.5 Baths
  • 6,050 SqFt

5750 Honest Point Ln, CHESTERTOWN

$2,750,000
24091 Providence Plantation Ln, CHESTERTOWN
  • Residential
  • 5 Beds
  • 5.5 Baths
  • 5,250 SqFt

24091 Providence Plantation Ln, CHESTERTOWN

$2,450,000 ↓ $120,000
24091 Providence Plantation Ln, CHESTERTOWN
  • Farm
  • 5 Beds
  • 5.5 Baths
  • 5,190 SqFt

24091 Providence Plantation Ln, CHESTERTOWN

$2,450,000 ↓ $120,000
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
23441 Cacaway Farm Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 3.5 Baths
  • 2,479 SqFt

23441 Cacaway Farm Ln, CHESTERTOWN

$925,000
0 Muirfield Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 0 SqFt

0 Muirfield Dr, CHESTERTOWN

$605,000 ↑ $20,000
114 Washington Ave, CHESTERTOWN
  • Residential
  • 5 Beds
  • 6 Baths
  • 4,100 SqFt

114 Washington Ave, CHESTERTOWN

$595,000
211 Landing Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 2,200 SqFt

211 Landing Ln, CHESTERTOWN

$595,000
108 Church Aly, CHESTERTOWN
  • Residential
  • 5 Beds
  • 1 Baths
  • 3,246 SqFt

108 Church Aly, CHESTERTOWN

$475,000 ↓ $40,000

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: $885,774
Total Listings: 39
Avg. Days On Market: 188
Avg. Price/SQFT: $283
Highest Price: $10,000,000
Lowest Price: $69,900
Avg. Property Age: 73 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 $900,000 - $1,000,000
Over $1,000,000
New
21363 Indiana Ave, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1 Baths
  • 896 SqFt

21363 Indiana Ave, CHESTERTOWN

$69,900
21317 Persimmon Dr #23, CHESTERTOWN
  • Residential
  • 2 Beds
  • 1 Baths
  • 1,269 SqFt

21317 Persimmon Dr #23, CHESTERTOWN

$121,900 ↑ $2,000
614 High St, CHESTERTOWN
  • Residential
  • 2 Beds
  • 1 Baths
  • 1,064 SqFt

614 High St, CHESTERTOWN

$129,500
511 High, CHESTERTOWN
  • Residential
  • 0 Beds
  • 0 Baths
  • 1,286 SqFt

511 High, CHESTERTOWN

$150,000
125 Conley Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 1,280 SqFt

125 Conley Dr, CHESTERTOWN

$171,000
102 Conley Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 1,280 SqFt

102 Conley Dr, CHESTERTOWN

$184,900
23730 Handy Point Rd, CHESTERTOWN
  • Residential
  • 0 Beds
  • 2 Baths
  • 1,998 SqFt

23730 Handy Point Rd, CHESTERTOWN

$219,000
209 Edmore Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 1,222 SqFt

209 Edmore Rd, CHESTERTOWN

$224,900
115 School Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2 Baths
  • 1,356 SqFt

115 School Rd, CHESTERTOWN

$235,000
106 Oak Leaf Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 1,976 SqFt

106 Oak Leaf Dr, CHESTERTOWN

$239,900
106 E Step Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2 Baths
  • 1,400 SqFt

106 E Step Rd, CHESTERTOWN

$245,000
810 Double Creek Point Road, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2 Baths
  • 1,400 SqFt

810 Double Creek Point Road, CHESTERTOWN

$250,000

Maryland Eastern Shore

Chestertown Real Estate

Chestertown Homes for Sale

Historic Chestertown is set on the banks of the Chester River on the Eastern Shore of Maryland. You will find boundless choices of Chestertown properties for sale. Downtown Chestertown offers historic homes on quiet streets, newer homes in nearby developments, waterfront communities and condos. Outside of town are properties in private settings, farms and stunning waterfront homes.

Chestertown is the second largest district of restored 18th-Century homes in Maryland. A prime example of the colonial architecture, at the corner of Water and High Streets is the 1770 Georgian Home, Widehall, built by Thomas Smythe. Smythe was a merchant who is believed to have been one of the area's richest citizens. The annual Chestertown Historic House Tour is held in September and is an opportunity to peek in and visit many of the area's historic homes owned by wealthy merchants in the 18th and 19th centuries. For more information about Chestertown and Kent County Tours please call (410) 778-2829.

Discover the Eastern Shore

Chestertown History

A Storied Past

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. In the mid-18th century, Chestertown was one of Maryland's leading ports and was named one of the colony's six Royal Ports of Entry.

Chestertown’s shipbuilding past has been revived through the non-profit Sultana Education Foundation offers 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 environment.

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, served as a trustee and received an honorary degree. Washington College is a great resource for Chestertown with access to senior programs and facilities.

Eastern Shore Living

Life in Chestertown

Visitors and residents alike are attracted to the area’s natural beauty and its peaceful, small town lifestyle combined with the convenience of being less than two hours from big city amenities. Enjoy the slower pace, walking along the tree-lined brick paths, and popping in to shops and galleries. Some of the local haunts are the Chester River Wine and Cheese Shop, Twigs and Teacups gift shop, Evergrain Bread bakery, Play it Again Sams Coffee Shop and Germaine's Carryout -New Orleans with a twist.

The Chester River Walk leads to waterfront dining at 98 Cannon Riverfront Grille and to The River Packet, a 65-foot classic yacht offering leisurely cruises on the Chester River. The area has many destinations to enjoy boating, hunting, crabbing and fishing, as well as walking and biking in parks and on trails.

Chestertown has a strong community sensibility and is home to many artists and musicians offering live theater and music performances. The Annual Chestertown Tea Party Festival is fun for everyone with folks in period dress, puppet shows, music, local fare and the wacky River Raft Race. The highlight of the weekend is a reenactment of the historic Tea Toss on the Sultana on the Chester River. In the Fall is the Sultana Downrigging Weekend with visiting tall ships offering tours, sailings and a beautiful evening illumination. Other events include the Harry Potter Festival and A Dickens Christmas. Link to information about local activities and events Town of Chestertown.

Find Your Eastern Shore Place

Get in Touch

Interested in finding out more about the area or a property? Richard can help - just call (443) 480-1181 or send an email.

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Bright MLS Logo© 2021 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 April 13th, 2021 at 8:46pm EDT.