Beautiful home in historic Chestertown. This property can be a single family home, or two separate units. The larger apartment features a gourmet kitchen with a beautiful wood-top island and stainless steel appliances. The kitchen leads to the large formal dining room, featuring the original stone fireplace, updated with a gas insert. The living space is designed for both comfortable living and effortless entertaining. During the winter, enjoy the wood burning fireplace in the living room, or warm up in the beautiful sunroom, just off of the living space. Downstairs there’s a full bathroom and bedroom, as well as a half-bath with laundry. Upstairs has a full bathroom and bedroom. Enter the upstairs apartment through the private entrance next to the driveway. the apartment has one bedroom, one bathroom, and a living room with hardwood floors. The large kitchen has room for a table, and plenty of natural light. Outside, a fenced-in yard with a covered patio offers a private oasis for relaxing evenings. The private driveway leads to a spacious barn garage with three barn doors. The barn offers ample storage, space for a small vehicle, or could be used as a workshop. Just a short distance from vibrant shops, restaurants, and the scenic Chester River waterfront. This home truly has it all, in the heart of Chestertown!
This duplex is a prime investment located on Washington Avenue in historic Chestertown, Maryland, offering many amenities. It is within walking distance of shopping, entertainment, schools, and medical facilities. Unit A is freshly updated with a spacious living room and dining room. The kitchen offers lots of storage and a stackable washer/dryer. It is a 2-bedroom apartment with a full bath. The floors are refinished hardwood. Unit B is a studio-style apartment with a full kitchenette. The 1-bedroom with a wooded view is a pleasant living space. A full bath is off the kitchen. It also offers access to a clean basement for extra storage. This rare find is a prime real estate investment for a home-based business, rental property, In-law suite, college students, or may even be easily converted back to a single-family home.Brand New Well Recently Installed. You could live on one side and rent the other! The possibilities are. endless. The Chester River and parks are right up the street for fishing/boating. Washington College is less than 1 mile away! Call for more details!
Prime Investment Opportunity in Chestertown with Leases In Place!!! This duplex property offers versatility, upgrades, and endless potential in a central Chestertown location. Conveniently situated across from Kent Plaza Shopping Center, near Washington College, and just minutes from the YMCA. This property is perfect for live-in owners, investors, or those seeking multi-use functionality .Excellent potential for a home business, in-law suite, or rental income from one or both units! With a prime location, countless upgrades, and flexibility, this diamond in the rough is ready to shine. Don't miss the opportunity to make it yours! Unit A: Bright & Spacious 2 Bed / 1 Bath This well-appointed 2-bedroom unit offers a comfortable and inviting living space. Large Living Room Area Updated kitchen with new Vinyl flooring and fixtures, perfect for cooking and separate Dining area. Convenient in-unit laundry with a stackable washer/dryer to simplify daily life. Refinished oak floors complemented by new ceiling fans, faucets, lights, receptacles and Freshly Painted for a polished look. Recently upgraded bathroom featuring Vinyl floor and a fresh design. Dedicated front parking for convenient and private access. Unit B: Modern 1 Bath Studio with Private Access This updated studio unit is ideal for a tenant seeking comfort, privacy, and convenience. With thoughtful renovations and modern upgrades. Private parking area with a safety light for added security and convenience. Dedicated side entrance featuring a new porch with safety rails and a durable cement base. Vinyl flooring throughout for a fresh and modern feel. Fully renovated kitchenette and bathroom, providing all the essentials in a sleek design. Exterior Highlights Newly installed apron driveway allows for seamless in-and-out access and parking around the house. Regraded landscaping with underground drainage ensures quick water management. New siding, trim, and gutter-guard gutters offer low-maintenance protection. Dependable pest/termite policy transferable to the new owner. Shed for additional storage Septic pumped and Well sealed in January 2025 for peace of mind. Registered with separate addresses for county emergency services. A wall divides the units but includes an existing door for easy conversion back to a single-family home if desired. Excellent potential for a home business, in-law suite, or rental income from one or both units!
A Rare Opportunity in the Heart of Historic Chestertown Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage. Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself. That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project. Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and business uses—making it an ideal candidate for those looking to merge lifestyle, business, and history. **See updated zoning info and description from town office in Documents. Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often. Schedule your showing today and imagine the future you can build here.
Chestertown is located in Maryland. Chestertown, Maryland has a population of 5,557. Chestertown is less family-centric than the surrounding county with 10.61% of the households containing married families with children. The county average for households married with children is 15.86%.
The median household income in Chestertown, Maryland is $44,665. The median household income for the surrounding county is $64,451 compared to the national median of $69,021. The median age of people living in Chestertown is 39.1 years.
The average high temperature in July is 87 degrees, with an average low temperature in January of 25.4 degrees. The average rainfall is approximately 45.1 inches per year, with 13.9 inches of snow per year.
