Chestertown

Chestertown Real Estate Listings
101 N Water St, CHESTERTOWN
  • Residential
  • 6 Beds
  • 6 Baths
  • 7,440 SqFt

101 N Water St, CHESTERTOWN

$4,400,000
400 River Rd, CHESTERTOWN
  • Residential
  • 5 Beds
  • 5 Baths
  • 7,932 SqFt

400 River Rd, CHESTERTOWN

$1,800,000
8039 Quaker Neck Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 3.5 Baths
  • 3,578 SqFt

8039 Quaker Neck Rd, CHESTERTOWN

$1,480,000 ↓ $70,000
7250 Pentridge Ln, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 0 SqFt

7250 Pentridge Ln, CHESTERTOWN

$1,450,000 ↓ $200,000
7250 Pentridge Ln, CHESTERTOWN
  • Farm
  • 4 Beds
  • 2.5 Baths
  • 0 SqFt

7250 Pentridge Ln, CHESTERTOWN

$1,450,000 ↓ $200,000
7755 Waterview Ln, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 4,730 SqFt

7755 Waterview Ln, CHESTERTOWN

$1,350,000
4652 Cliffs City Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2 Baths
  • 2,691 SqFt

4652 Cliffs City Rd, CHESTERTOWN

$945,000 ↑ $70,000
408 Pear Tree Point Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 2,782 SqFt

408 Pear Tree Point Rd, CHESTERTOWN

$887,000
9831 Breezecroft Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 3.5 Baths
  • 2,352 SqFt

9831 Breezecroft Ln, CHESTERTOWN

$859,000
954 High St, CHESTERTOWN
  • Residential
  • 6 Beds
  • 6 Baths
  • 6,334 SqFt

954 High St, CHESTERTOWN

$795,000 ↓ $30,000
456 Pear Tree Point Rd, CHESTERTOWN
  • Residential
  • 2 Beds
  • 2 Baths
  • 1,834 SqFt

456 Pear Tree Point Rd, CHESTERTOWN

$750,000
114 N Water St, CHESTERTOWN
  • Residential
  • 4 Beds
  • 3.5 Baths
  • 3,640 SqFt

114 N Water St, CHESTERTOWN

$749,000

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: $564,707
Total Listings: 58
Avg. Days On Market: 95
Avg. Price/SQFT: $211
Highest Price: $4,400,000
Lowest Price: $59,000
Avg. Property Age: 54 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
7968 Aldan Dr, CHESTERTOWN
  • Residential
  • 5 Beds
  • 3.5 Baths
  • 5,200 SqFt

7968 Aldan Dr, CHESTERTOWN

$689,000
421 Pear Tree Point Rd W, CHESTERTOWN
  • Residential
  • 2 Beds
  • 1 Baths
  • 997 SqFt

421 Pear Tree Point Rd W, CHESTERTOWN

$249,000
203 Silver Heel Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 3,080 SqFt

203 Silver Heel Rd, CHESTERTOWN

$399,900
New
108 S Mill St, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 2,114 SqFt

108 S Mill St, CHESTERTOWN

$435,000
305 Cedar, CHESTERTOWN
  • Residential
  • 2 Beds
  • 1.5 Baths
  • 2,134 SqFt

305 Cedar, CHESTERTOWN

$310,000
111 S College Ave, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 1,600 SqFt

111 S College Ave, CHESTERTOWN

$329,900 ↓ $10,000
9540 Fairlee Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2 Baths
  • 2,795 SqFt

9540 Fairlee Rd, CHESTERTOWN

$499,900
143 Fairview Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1 Baths
  • 1,026 SqFt

143 Fairview Dr, CHESTERTOWN

$198,000
8939 Orchard, CHESTERTOWN
  • Residential
  • 4 Beds
  • 3 Baths
  • 2,905 SqFt

8939 Orchard, CHESTERTOWN

$580,000
206 Birch Run Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 2,334 SqFt

206 Birch Run Rd, CHESTERTOWN

$425,000
9850 Fairlee Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1 Baths
  • 1,120 SqFt

9850 Fairlee Rd, CHESTERTOWN

$264,900
400 River Rd, CHESTERTOWN
  • Residential
  • 5 Beds
  • 5 Baths
  • 7,932 SqFt

400 River Rd, CHESTERTOWN

$1,800,000

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 October 27th, 2021 at 6:45am EDT.