Vintage homes for sale & real estate in Chestertown, MD

Vintage Home 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

Vintage Home for sale in Chestertown, MD:

Seller offering up to $5,000 in closing cost assistance with accepted offer. Welcome to 115 Cemetery Lane, a charming home nestled in the quiet and friendly community of Church Hill, MD. This inviting property features 3 bedrooms and 2 full bathrooms, offering comfortable single-level living with a thoughtful layout. Step inside to a bright, open-concept living area with large windows that fill the space with natural light. The kitchen boasts ample cabinetry, modern appliances, and plenty of counter space perfect for home-cooked meals or entertaining. The primary suite includes a private bath and generous closet space, while additional bedrooms are ideal for guests, a home office, or family

Vintage Home for sale in Chestertown, MD:

This home has been meticulously maintained and is located in the heart of everything Rock Hall has to offer! The 2 story entrance foyer with tile floors is just the beginning of the surprise you will find in this special, 2,900+/- square foot, home. There are 4 bedrooms, 3.5 baths, a large living room with cathedral ceiling, 2 bedrooms upstairs and 2 bedrooms down, heat pump and mini-split systems for heating and cooling and is move in ready!! A free standing propane stove will help take the chill off during the cooler months. The dining area is just off the kitchen with great views from the large picture window. The kitchen offers all of the major appliances. The laundry room is also a v

Vintage Home for sale in Chestertown, MD:

Originally built with handcrafted bricks in 1782, this Flemish Bond Georgian Colonial home is the embodiment of simple elegance. Restored with the utmost historical respect in the mid-1980’s with handcrafted oak windows and mahogany doors with period hardware and modernized with preservation-sensitive practices and materials over the past eight years by the current stewards of the home, step into the past while enjoying today’s comforts. The four-bay home has a traditional floor plan with the living and dining room flanking the center hall, a large sunken family room anchored by the massive hearth – reconstructed with original bricks from the 1782 structure and walnut mant

Vintage Home for sale in Chestertown, MD:

Original Primary School No. 3 | c. 1840 | Near Kennedyville Featured in Historic Homes of Kent County Step back in time with this one-of-a-kind historic treasure — the original Primary School No. 3, circa 1840, lovingly preserved and waiting for its next chapter. Listed in Historic Homes of Kent County, this unique property sits on just under two acres, offering timeless charm, unmatched character, and rare opportunity. Set back from the road and tucked along tree-lined boundaries, the home offers exceptional privacy while evoking a deep sense of history. As you walk through the home, original details greet you at every turn — from the beloved deep window sills and antique newel

Vintage Home for sale in Chestertown, MD:

Vintage home with lots of original details retained. 3 Staircases, 3 original fireplaces and a very grand front foyer and staircase give this home so much character! Current owners have updated it lovingly throughout. Enter through the spacious back yard, into a welcoming mudroom with a full bath on the main floor to your left and then into the updated and cozy kitchen with new dishwasher, LVP flooring, complete with the cutest back stair case! The staircase leads up to a separate home office, craft room, den, or 4th bedroom. Also downstairs is a main floor bedroom, a nice size dining room with decorative fireplace and parquet flooring, and a Living room with new carpet, and a new pellet