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

6324 Quaker Neck Rd, Chestertown $2,895,000

Discover 6324 Quaker Neck Road, an exceptional waterfront estate spanning over 5 acres along the East Fork of Langford Creek offering over 5 feet of water at low tide. Ov...

5 Beds
4 Baths

Courtesy of Cross Street Realtors LLC

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

22974 Bay Shore Rd, Chestertown $329,900

Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farm...

2 Beds
2 Baths

Courtesy of Benson & Mangold, LLC

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

7712 Waterview Ln, Chestertown $659,999

Live where you play at 7712 Waterview Lane in sought-after Country Club Estates. Situated on just under an acre, this beautifully renovated, well-maintained Cape Cod is ...

3 Beds
4 Baths

Courtesy of Coldwell Banker Chesapeake Real Estate Company

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

8732 Elm Rd, Chestertown $289,000

Located in Tolchester Estates, this well maintained ranch style home sits on a lovely tree shaded lot. There are three bedrooms, two bathrooms and an open kitchen, dining...

3 Beds
2 Baths

Courtesy of Coldwell Banker Chesapeake Real Estate Company

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

8276 Broad Neck Rd, Chestertown $1,295,000

Step into your own private world, just 2.75 miles from Historic Downtown Chestertown. Tucked away at the rear of a mostly wooded 19+/- acre parcel, this exceptionally wel...

4 Beds
4 Baths

Courtesy of Select Land & Homes, LLC

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956

223 Mount Vernon Ave, Chestertown $200,000

Investors, contractors & handy buyers—this is the fixer-upper opportunity you’ve been waiting for! This downtown Chestertown diamond in the rough offers strong ARV potent...

4 Beds
1 Baths

Courtesy of Chesapeake Real Estate Associates, LLC

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

7415 Wilkins Ln, Chestertown $229,000

This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property f...

3 Beds
1 Baths

Courtesy of Doug Ashley Realtors, LLC

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

7482 Poplar Ave, Chestertown $275,000

Welcome home! This beautifully maintained and updated property sits on a generous .45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added...

3 Beds
1 Baths

Courtesy of Taylor Properties

Listing courtesy of Taylor Properties. Contact:

24775 Langford Rd, Chestertown $315,000

Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The pro...

3 Beds
1 Baths

Courtesy of RE/MAX Chesapeake

Listing courtesy of RE/MAX Chesapeake. Contact:

104 Lincoln Dr, Chestertown $295,000 ▼

This adorable rancher combines a fresh, updated interior with plenty of outdoor space to enjoy. Come step inside to a bright and welcoming home filled with natural light,...

3 Beds
1 Baths

Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact: 4432741900

212 Washington Ave, Chestertown $675,000

Welcome home to historic Chestertown. This beautiful 5 bedroom colonial is located just one block from Washington College. Relax on your welcoming mahogany front porch be...

5 Beds
3 Baths

Courtesy of Coldwell Banker Chesapeake Real Estate Company

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

300 and 302 S Mill St, Chestertown image

300 and 302 S Mill St, Chestertown $1,195,000

Remarkable 1 acre downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homes...

2 Beds
1 Baths

Courtesy of Coldwell Banker Chesapeake Real Estate Company

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