Downtown Chestertown Homes for Sale

Downtown Chestertown Homes for Sale

Welcome to Downtown Chestertown, a charming enclave nestled in the heart of Kent County, Maryland. This picturesque town, steeped in history and brimming with character, offers a unique blend of small-town charm and vibrant community life. With its cobblestone streets, historic buildings, and waterfront views along the Chester River, Downtown Chestertown is a delightful place to call home.

As you explore the area, you'll discover a rich tapestry of shops, restaurants, and cultural attractions that make this community truly special. From quaint boutiques to local eateries serving up delicious farm-to-table cuisine, there's always something new to experience. The town is also home to several annual events and festivals, fostering a strong sense of community among residents and visitors alike.

For those looking to settle down in this idyllic setting, Downtown Chestertown offers a variety of homes for sale that cater to diverse tastes and lifestyles. Whether you're searching for a charming historic home with period details or a modern townhouse with contemporary amenities, you'll find an array of options that fit your needs. Many properties boast stunning views of the river or are conveniently located within walking distance to local attractions, making it easy to immerse yourself in the vibrant culture of the town.

With its rich history, thriving community, and beautiful homes, Downtown Chestertown is a hidden gem waiting to be discovered. Come and explore the possibilities of making this enchanting town your new home!

Newest Downtown Chestertown Homes for Sale

108 N Water St, Chestertown
$1,125,000
5 Beds ⋅ 4 Baths
This 1925 classic colonial, three story residence, with both front and back gardens, is uniquely situated in the center of the favored 100 block of North Water Street, in historic Chestertown. The formal main entry, with dual brick steps approaches a generous landing, faces away from the street. At first a curiosity until you learn that a prominent family discovered the architectural plans for their "dream house" would not fit horizontally to face the prized road. During its' 100-plus years of life, the front porch (or was it the side?) was converted to a remarkable library, with requisite bookcases, and enjoys light from three sides. The formal parlor, with wood-burning fireplace and reclaimed 19th century moldings and mantle, is left of the straight-through center hall with classic black and white porcelain tiles. The intimate, yet well-proportioned dining room enhances the exceptional flow of the first-floor public rooms. A discreetly positioned powder room and butler's pantry with window and original cabinetry is conveniently placed before entering the large and sunny kitchen with premium custom cabinetry, appliances and finishes from a 2012 renovation. Two distinct patios, one screened and accessed from the dining room and the other from kitchen, overlook the large, rear garden with mature trees and landscaping. The center stairs, with a palladium window bathing light onto the steps, takes you to the first of two oversized landings that have served many lifestyle-uses over the years. The water view primary suite was renovated in 2022 by locally acclaimed Taylor Loughry LLC and boasts a timeless, luxurious aesthetic with custom built closets and Waterwork bath fixtures. Two additional bedrooms and refreshed bath with Restoration Hardware finishes, occupy the second floor. The third floor, with its own generous landing gives access to an ensuite bedroom with walk-in windowed closet (perfect for a future cedar lined closet) and a substantial sized fifth bedroom or multi-purpose space facing the Chester River and exquisite neighboring architecture. Rear yard might accommodate a pool.

108 N Water St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

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