Downtown Chestertown Homes with Colonial Style

Downtown Chestertown Homes with Colonial Style

Welcome to Downtown Chestertown, a charming gem nestled in the heart of Kent County, Maryland. This historic town, with its picturesque streets and vibrant community spirit, offers a unique blend of small-town charm and modern conveniences. Known for its rich history, Downtown Chestertown features beautifully preserved colonial architecture that transports you back in time while providing the comforts of contemporary living.

As you stroll through the tree-lined streets, you’ll be captivated by the stunning colonial-style homes that define the neighborhood. These residences boast classic features such as symmetrical facades, gabled roofs, and elegant brickwork, each telling its own story of the town's storied past. The spacious layouts and high ceilings of these colonial homes create inviting spaces perfect for both family gatherings and entertaining friends. Many properties come with lush gardens and outdoor spaces, allowing you to enjoy the beauty of nature right at your doorstep.

Beyond the beautiful homes, Downtown Chestertown is a vibrant hub of activity. The area is dotted with quaint shops, delightful cafes, and art galleries, making it a perfect place to explore. Residents enjoy easy access to the Chester River, where you can indulge in various recreational activities such as kayaking, fishing, and leisurely boat rides.

Whether you’re seeking a charming family home or a cozy retreat, Downtown Chestertown offers a unique lifestyle enriched by history, community, and natural beauty. Discover the allure of colonial living in this enchanting town, where every day feels like a step back in time.

Newest Downtown Chestertown Homes with Colonial Style

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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