Chestertown Real Estate

Welcome to Chestertown, Maryland—a charming riverside town that beautifully blends history, culture, and a vibrant community spirit. Nestled in Kent County along the scenic Chester River, Chestertown offers a picturesque setting that captivates both residents and visitors alike.

Founded in the 18th century, this historic town boasts a rich heritage, with well-preserved architecture that transports you back in time. Stroll along the cobblestone streets and admire the elegant Georgian and Federal-style homes, many of which date back to the colonial era. The town's commitment to preserving its history is evident in landmarks like the Chestertown Historic District, which is listed on the National Register of Historic Places.

Chestertown is not just about history; it's a hub for arts and culture. The town hosts a variety of events throughout the year, including the renowned Chestertown Tea Party Festival, celebrating its revolutionary roots, and the RiverArts organization, which showcases local artists and craftspeople. Outdoor enthusiasts will find plenty to love here, too. The Chester River offers opportunities for kayaking, sailing, and fishing, while the surrounding countryside invites hiking and biking adventures.

With a friendly, close-knit community, Chestertown is a place where neighbors become friends. Families are drawn to its excellent schools and safe environment, while retirees enjoy the serene pace of life. Whether you’re looking to settle down or simply visit, Chestertown welcomes you with open arms and a promise of unforgettable experiences. Come explore this hidden gem on Maryland's Eastern Shore, where history meets hospitality!

Newest Listings in Chestertown

104 Maple Ave, Chestertown $595,000

List price is opening bid at online auction to be conducted on auctioneer's website. Online Auction Only! Bidding begins Saturday, November 28 and ends Thursday, Decembe...

Courtesy of Alex Cooper Auctioneers, Inc.

Listing courtesy of Alex Cooper Auctioneers, Inc.. Contact:

7570 Muirfield Dr, Chestertown $895,000

Elegant Golf Course Living on Maryland’s Eastern shore. Experience the understated elegance of Eastern Shore living in this beautifully crafted, custom-built residence o...

4 Beds
3 Baths

Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

818 High St, Chestertown $3,300,000

Prime Commercial Opportunity in Chestertown!! The Brian E. Bainbridge Health Building is a prominent, three-story commercial property offers 23,000 square feet of versati...

Courtesy of Coldwell Banker Chesapeake Real Estate Company

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

111 Kent St S, Chestertown $450,000

Nestled in the heart of the Chestertown Historic District, this exquisite residence offers a harmonious blend of traditional charm and modern luxury. Built in 2008, this ...

2 Beds
3 Baths

Courtesy of Doug Ashley Realtors, LLC

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

403 Calvert St, Chestertown $135,000

INVESTOR OPPORTUNITY! Come see this 3-bedroom, 1.5-bath townhome offering great potential to add to your portfolio! Recent improvements include drywall replacement, newly...

3 Beds
2 Baths

Courtesy of Chesapeake Real Estate Associates, LLC

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

201 Garland Way, Chestertown $375,000

Discover a prime investment opportunity in the sought-after Coventry Farms subdivision! This charming Colonial-style home, built in 2010, boasts 2,886 square feet of pote...

4 Beds
3 Baths

Courtesy of ERA Martin Associates

Listing courtesy of ERA Martin Associates. Contact:

108 N Water St, Chestertown $1,125,000

This 1925 classic colonial, three story residence, with both front and back gardens, is uniquely situated in the center of the favored 100 block of North Water Street, in...

5 Beds
4 Baths

Courtesy of Cross Street Realtors LLC

Listing courtesy of Cross Street Realtors LLC. Contact:

7545 Quaker Neck Rd, Chestertown $175,000

Needs work. Sold as is

3 Beds
1 Baths

Courtesy of Thurston Wyatt Real Estate, LLC

Listing courtesy of Thurston Wyatt Real Estate, LLC. Contact:

501 High St, Chestertown $349,900

Investor Alert in Historic Downtown Chestertown! Fully Occupied Triplex. Units offer hardwood floors, mini splits to units 1 and 2, a new bathroom in unit 3 and kitchen u...

Courtesy of Chesapeake Real Estate Associates, LLC

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

8668 Elm Rd, Chestertown $349,900

Brand new construction in water oriented Tolchester Estates located on the Chesapeake Bay. 4 Bedroom, 2 bath Cape Cod on a wooded lot and quiet neighborhood. Community o...

4 Beds
2 Baths

Courtesy of Kevin Dey Realty

Listing courtesy of Kevin Dey Realty. Contact:

7655 James Ln, Chestertown $519,900

Enjoy a peaceful country setting at 7655 James Lane. Situated on a two-acre lot along a quiet cul-de-sac street, this well-maintained ranch home offers approximately 2,47...

3 Beds
3 Baths

Courtesy of RE/MAX Advantage Realty

Listing courtesy of RE/MAX Advantage Realty. Contact:

24607 Chestertown Rd, Chestertown $365,000

Enjoy the best of both worlds with this well-maintained home situated on a generous 0.653-acre lot just outside of Chestertown! Offering the space and privacy of country ...

3 Beds
3 Baths

Courtesy of Coldwell Banker Chesapeake Real Estate Company

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact: