Homes with Basements for Sale in Chestertown, MD

Home with Basement for sale in Chestertown, MD:

Investor Opportunity with Historic Charm in Sudlersville If you’ve been waiting for a project with real character, this is the one. This large Victorian is full of potential and just waiting for the right vision to bring it back to life. From the moment you see the wide front porch, you can imagine slow mornings with coffee, quiet evenings with tea, and the timeless charm this home once offered—and can offer again. Set on a generous lot just outside the heart of Sudlersville, the property blends small-town charm with everyday convenience. You’re minutes from Route 301, making commuting or travel simple while still enjoying a quieter pace of life. The home is equipped with

Home with Basement for sale in Chestertown, MD:

Welcome to this charming 3-bedroom rancher in the quaint town of Rock Hall. Featuring beautiful wood floors throughout, this cozy home is being sold as-is—perfect for buyers looking to add their own personal touch. A standout feature is the detached garage with a bathroom rough-in, currently used as an entertainment space or “man cave. ” With a few updates, it could easily be transformed into a studio, home office, or “she shack, ” providing flexible space to suit your lifestyle. Recent improvements include newer kitchen appliances, a new HVAC system, a 6' vinyl privacy fence, and a tankless water heater (ready for installation). The oversized garage offers gen

Home with Basement for sale in Chestertown, MD:

Welcome to 530 Kennersley Farm Lane, nestled in the private waterfront community of Kennersley Farm. Set on 5 private acres along Island Creek, this property offers lots of privacy and nature. A long, tree-lined driveway leads you past mature landscaping and ample parking, where you can see views of the water. Inside, there is beautiful flooring and a bright, open layout. The kitchen features granite countertops, a center island, upgraded GE Profile appliances, and an eat-in area overlooking the in-ground pool and Island Creek. The primary suite, located on the first floor, is a true retreat with a huge walk-in closet, featuring a soaking tub, dual granite vanity, and tile shower. This roo

Home with Basement for sale in Chestertown, MD:

If you’ve been looking for a home you can truly make your own, this is the opportunity. This property offers a large, open floor plan with all the square footage and layout you’ve been wanting. It simply needs the right buyer to bring it back to life. Inside, you’ll find a dedicated office, a formal dining room, and an expansive kitchen and family room that make everyday living and entertaining effortless. Upstairs, all 4 bedrooms are generously sized, including a massive primary suite complete with a large bathroom and a huge walk-in closet. The full basement offers even more potential — whether you envision a rec room, gym, theater, or additional living space, it&r

Home with Basement for sale in Chestertown, MD:

Tucked away along the quiet shores of Still Pond Creek, this cedar cabin offers a rare blend of privacy, comfort, and natural beauty. Surrounded by mature woods and set on a peaceful stretch of waterfront, this 1,944 square foot home features 3 bedrooms, 2 bathrooms, a spacious screened-in porch perfect for crab feasts, a private beach and pier with 2'+ MLW improved with bilk head installed by Army Corps. Whether you’re seeking a weekend retreat or a year-round escape, this property captures the essence of Eastern Shore living—simple, timeless, and immersed in nature where mind, body, and soul find balance.

Home with Basement for sale in Chestertown, MD:

Located along Shipyard Creek just outside Rock Hall, this 113-acre farm offers a strong combination of productive soils, waterfront access, and long-term investment value. The property includes approximately 100 tillable acres with primarily Mattapex soils— moderately well-drained and highly rated for grain and forage production. The balance consists of woodland providing natural buffers between the creek and fields as well as quality wildlife habitat. Improvements include a 3,200 square foot Colonial Revival home and versatile shop. Both lay along 1,500 feet of shoreline steps away from a private dock offering 4'+ MLW. Farms of this size and quality rarely become available in Kent Co