Chestertown Homes for Sale

Welcome to Chestertown, Maryland – a hidden gem nestled in the heart of Kent County. This charming town, steeped in rich history and vibrant culture, offers a picturesque blend of small-town charm and modern amenities. With its scenic waterfront along the Chester River, Chestertown is a haven for nature lovers and outdoor enthusiasts. Stroll along the historic streets lined with 18th-century buildings, quaint shops, and delightful cafes, or enjoy a leisurely afternoon at one of the local parks.

Chestertown is not just a feast for the eyes; it’s also a thriving community filled with friendly faces and engaging events. The town hosts a variety of festivals throughout the year, including the renowned Chestertown Tea Party Festival, celebrating the town's revolutionary spirit. Additionally, the local arts scene is flourishing, with galleries and theaters showcasing the talents of both established and emerging artists.

For those looking to find their dream home, Chestertown offers an array of beautiful properties for sale. From charming historic homes with unique architectural details to modern residences with all the latest conveniences, there’s something to suit every lifestyle and budget. Many of these homes boast stunning views of the river or are conveniently located near the vibrant downtown area, allowing residents to enjoy all the best that Chestertown has to offer.

Whether you’re seeking a peaceful retreat or a vibrant community to call home, Chestertown, MD, is the perfect place to start your next chapter. Explore the homes for sale today and discover the enchanting lifestyle that awaits you in this delightful town!

Newest Chestertown Homes for Sale

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:

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:

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:

317 Rolling Rd, Chestertown $229,900

Located in the College Heights neighborhood of Chestertown, this 3-bedroom, 2-bath home is situated on a .34± acre lot and is full of potential! Enjoy the convenience of ...

3 Beds
2 Baths

Courtesy of Select Land & Homes, LLC

Listing courtesy of Select Land & Homes, 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:

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:

8901 S Bayview Dr, Chestertown $525,000

The Perfect Maryland Retreat with Chesapeake Bay Views Close By. Experience the quality of a custom-built Cape Cod crafted by a reputable local builder. Lovingly maintai...

3 Beds
3 Baths

Courtesy of Doug Ashley Realtors, LLC

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

21338 Virginia Ave, Chestertown $400,000

Nestled in the quiet Tolchester Estates, this charming new construction home, completed in 2026, embodies the pinnacle of low maintenance living. This well-built ranch-st...

2 Beds
2 Baths

Courtesy of Doug Ashley Realtors, LLC

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

106 Harlan Loop, Chestertown $425,000

Nestled in Coventry Farms II, this exquisite Colonial-style residence offers a harmonious blend of Space, Convenience and comfort, perfect for those who appreciate the fi...

4 Beds
3 Baths

Courtesy of Douglas Realty LLC

Listing courtesy of Douglas Realty LLC. Contact:

8986 Orchard Dr, Chestertown $679,900

Welcome to 8986 Orchard Drive, tucked away in the sought-after Orchard Hill neighborhood just outside of Chestertown! This move-in-ready home offers comfortable one-level...

3 Beds
4 Baths

Courtesy of Benson & Mangold, LLC

Listing courtesy of Benson & Mangold, LLC. Contact: