Downtown Chestertown Homes with Front Yard Lot Description

Downtown Chestertown Homes with Front Yard Lot Description

Welcome to Downtown Chestertown, a charming neighborhood nestled in the heart of Kent County, Maryland. This picturesque area is steeped in history, showcasing beautifully preserved 18th-century architecture alongside modern amenities, making it a perfect blend of old-world charm and contemporary living.

As you stroll through the tree-lined streets of Downtown Chestertown, you’ll discover a vibrant community filled with local shops, delightful eateries, and a rich cultural scene. The nearby Chester River adds to the area's allure, offering stunning waterfront views and opportunities for boating, fishing, and leisurely walks along the scenic waterfront park.

One of the standout features of homes in Downtown Chestertown is the abundance of properties with front yard lots. These homes often boast manicured lawns and charming gardens, inviting residents to enjoy the outdoors right from their doorstep. Imagine sipping your morning coffee on a sunny porch or hosting a barbecue with friends in your spacious front yard. The community spirit is palpable here, as neighbors gather to enjoy the beauty of their surroundings.

Whether you’re a first-time homebuyer, looking to downsize, or seeking a peaceful retreat, Downtown Chestertown offers a variety of housing options to suit your needs. With its friendly atmosphere, rich history, and a strong sense of community, it’s no wonder that this area is highly sought after. Come explore the delightful homes with front yard lots in Downtown Chestertown and discover your perfect slice of Maryland living!

Newest Downtown Chestertown Homes with Front Yard Lot Description

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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