Downtown Chestertown Homes with River View

Downtown Chestertown Homes with River View

Welcome to Downtown Chestertown, a charming and vibrant community nestled in the heart of Kent County, Maryland. Known for its rich history and picturesque waterfront, this delightful town offers a unique blend of small-town charm and modern amenities, making it an ideal place to call home.

One of the most enchanting features of Downtown Chestertown is its stunning river views. Imagine waking up each morning to the gentle sounds of the Chester River, with its shimmering waters reflecting the changing colors of the sky. Homes in this area are thoughtfully designed to take full advantage of these breathtaking vistas, allowing residents to enjoy serene sunsets and the soothing ambiance of riverside living.

Downtown Chestertown boasts a variety of architectural styles, from historic colonial homes to contemporary designs, all infused with character and warmth. Many properties come equipped with spacious decks or patios, perfect for entertaining guests or simply unwinding while soaking in the views. The sense of community here is palpable, with friendly neighbors and a welcoming atmosphere that makes it easy to feel at home.

In addition to its beautiful homes, Downtown Chestertown offers a wealth of local attractions. Stroll along the charming streets lined with boutique shops, art galleries, and delightful eateries, or take part in the vibrant cultural events that showcase the town's artistic spirit. Outdoor enthusiasts will appreciate the nearby parks and recreational opportunities, including kayaking, fishing, and hiking along the scenic riverbanks.

Whether you’re looking to settle down or invest in a vacation getaway, Downtown Chestertown with its river view homes offers a perfect blend of tranquility and convenience. Come experience the magic of this remarkable community today!

Newest Downtown Chestertown Homes with River View

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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