Downtown Chestertown Homes for Sale

Downtown Chestertown Homes for Sale

Welcome to Downtown Chestertown, Maryland, a charming and historic gem nestled in the heart of Kent County. Known for its picturesque waterfront views and vibrant community, Downtown Chestertown offers a unique blend of small-town charm and modern convenience. Stroll along the quaint streets lined with beautifully preserved 18th-century buildings, boutique shops, and delightful eateries, all while soaking in the rich history that this area has to offer.

As you explore Downtown Chestertown, you’ll find a diverse selection of homes for sale that cater to various lifestyles and preferences. From cozy historic homes that echo the town's storied past to contemporary residences boasting modern amenities, there’s something for everyone in this inviting community. Many homes feature spacious yards, perfect for outdoor gatherings, while others offer stunning views of the Chester River, allowing you to enjoy the serene beauty of nature right from your doorstep.

Living in Downtown Chestertown means you’re just steps away from local events, farmers' markets, and cultural festivals that bring the community together. Enjoy the vibrant arts scene, with galleries and theaters showcasing local talent, or take a leisurely walk along the riverfront, where you can watch boats glide by and soak up the tranquil atmosphere.

With homes for sale in Downtown Chestertown, you’re not just investing in a property; you’re becoming part of a welcoming community that values history, connection, and the simple joys of life. Discover your dream home in this enchanting town and experience the best of Maryland living!

Newest Downtown Chestertown Homes for Sale

234 N Kent St, Chestertown
$325,000
5 Beds ⋅ 2 Baths
Some houses are finished. This one is full of opportunity. Built circa 1920, this Victorian sits in one of Downtown Chestertown's most desirable neighborhoods — and it's waiting for someone who can see what it is meant to become. The hard work and the expensive work have already been done: new cedar siding, blown-in insulation, and original hardwood floors throughout. What remains is the fun part. The kitchen and baths are a genuine blank slate, ready for your design, your finishes, your vision. And the bones… remarkable. Solid construction, generous proportions, and historic detail at every turn — the kind of craftsmanship that simply isn't built anymore, and can't be bought back once it's gone. Start with a house of real character and your renovation adds value instead of merely keeping up. Upstairs, five generous bedroom and two full baths. A rare third-floor primary suite offers space and privacy set apart from the rest of the home — a true owner's retreat, a guest wing, or a quiet work-from-home floor of its own. Outside, a fully fenced backyard is ready for pets, play, and entertaining, a large shed could easily become a garage, studio, or workshop. The driveway provides off-street parking, a definite bonus for Chestertown. And the location is the whole point. You're roughly three blocks from everything Chestertown offers — the shops, restaurants and galleries along High Street, the Chester River waterfront, the farmers market, and the historic charm of one of the Eastern Shore's best-loved small towns. Bring your contractor, or be your own. Come see the possibility.

234 N Kent St, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

Start Your Search