Chestertown Townhomes for Sale

Welcome to Chestertown, Maryland—a hidden gem nestled in the heart of Kent County, where history and charm intertwine seamlessly. This picturesque town, located along the banks of the Chester River, boasts a vibrant arts scene, rich colonial heritage, and a welcoming community spirit that draws visitors and residents alike. With its historic architecture, quaint shops, and delightful eateries, Chestertown offers a unique blend of small-town charm and modern conveniences.

For those seeking a new home in this enchanting town, look no further than the stunning townhomes for sale in Chestertown. These beautifully designed residences provide the perfect balance of comfort and sophistication, catering to a variety of lifestyles. Imagine waking up in your spacious townhome, bathed in natural light, with views of the lush landscapes that surround you. Many of these properties feature open floor plans, gourmet kitchens, and private outdoor spaces—ideal for entertaining friends or simply enjoying a quiet evening at home.

Living in Chestertown means embracing a lifestyle filled with outdoor adventures, from kayaking on the Chester River to exploring the scenic trails of nearby parks. The town is also home to a number of annual events, including the renowned Chestertown Tea Party Festival, which celebrates the town’s rich history and community spirit.

With its inviting atmosphere and beautiful townhomes for sale, Chestertown is not just a place to live; it’s a place to thrive. Discover your dream home in this charming town and become part of a community that values history, culture, and the beauty of life along the river.

Newest Chestertown Townhomes for Sale

104 Church Aly, Chestertown $440,000

A perfect pied-a-terre or full time residence, this adorable historic home is just steps from the farmers market, shops, restaurants, theater,art galleries and the Cheste...

2 Beds
2 Baths

Courtesy of Coldwell Banker Chesapeake Real Estate Company

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

115 Metcalf Rd, Chestertown $259,900

Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitch...

3 Beds
2 Baths

Courtesy of Real Broker, LLC - Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

107 Conley Dr, Chestertown $240,000

Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable locatio...

3 Beds
1 Baths

Courtesy of Benson & Mangold, LLC

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

121 Metcalf Rd, Chestertown $264,900

Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with ...

3 Beds
2 Baths

Courtesy of Real Broker, LLC - Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

21324 Persimmon Dr, Chestertown $189,000 ▼

Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, thi...

2 Beds
1 Baths

Courtesy of Benson & Mangold, LLC

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

409 Calvert St, Chestertown $155,000

Affordable opportunity in the heart of downtown Chestertown! This 3-bedroom, 1.5-bath townhome is ideally located just minutes from Washington College, shops, restaurants...

3 Beds
2 Baths

Courtesy of Chesapeake Real Estate Associates, LLC

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

104 Conley Dr, Chestertown $239,900 ▼

Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, lo...

3 Beds
2 Baths

Courtesy of Cummings & Co. Realtors

Listing courtesy of Cummings & Co. Realtors. Contact: 4108230033

104 Acorn Dr, Chestertown $275,000 ▼

Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly posi...

3 Beds
3 Baths

Courtesy of Cross Street Realtors LLC

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

226 S Water St, Chestertown $898,000

Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner ...

3 Beds
4 Baths

Courtesy of Gunther-McClary Real Estate

Listing courtesy of Gunther-McClary Real Estate. Contact:

#36 Landing Ln, Chestertown $753,500

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The h...

3 Beds
3 Baths

Courtesy of Gunther-McClary Real Estate

Listing courtesy of Gunther-McClary Real Estate. Contact:

#35 Landing Ln, Chestertown $786,900

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The ...

3 Beds
3 Baths

Courtesy of Gunther-McClary Real Estate

Listing courtesy of Gunther-McClary Real Estate. Contact:

104 Landing Ln, Chestertown $813,900

**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The ...

3 Beds
4 Baths

Courtesy of Gunther-McClary Real Estate

Listing courtesy of Gunther-McClary Real Estate. Contact: