Chestertown Historic District Homes for Sale

Chestertown Historic District Homes for Sale

Welcome to the enchanting Chestertown Historic District, a hidden gem nestled in the heart of Kent County, Maryland. This charming area is renowned for its rich history, picturesque streets, and vibrant community spirit. Established in the 18th century, Chestertown boasts beautifully preserved architecture that tells the story of its colonial past, making it a delightful place for history enthusiasts and modern-day homeowners alike.

As you stroll through the tree-lined streets, you’ll encounter an array of stunning homes, each with its own unique character. From stately Federal-style houses to quaint Victorian cottages, the Chestertown Historic District offers a diverse selection of properties that cater to various tastes and lifestyles. Many of these homes feature original details such as hardwood floors, decorative moldings, and inviting porches, providing a perfect blend of historic charm and contemporary comfort.

For those looking to invest in this charming community, there are homes for sale that present an incredible opportunity to become part of the Chestertown legacy. Picture yourself living just steps away from the beautiful Chester River, where you can enjoy leisurely walks, boating, and vibrant local festivals. The district is also home to delightful shops, art galleries, and restaurants that showcase the best of local culture and cuisine.

With its stunning scenery, rich historical significance, and a warm, welcoming community, the Chestertown Historic District is more than just a place to live; it’s a lifestyle. Come explore the homes for sale in this captivating neighborhood and discover the perfect blend of history and modern living. Your dream home awaits!

Newest Chestertown Historic District Homes for Sale

111 Kent St S, Chestertown
$450,000
2 Beds ⋅ 3 Baths
Nestled in the heart of the Chestertown Historic District, this exquisite residence offers a harmonious blend of traditional charm and modern luxury. Built in 2008, this detached home stands as a testament to meticulous craftsmanship and thoughtful design, ensuring an exceptional living experience. Step inside to discover an open floor plan that invites natural light to dance across the spacious interiors. The heart of the home features a cozy gas fireplace, perfect for creating warm, inviting gatherings. The well-appointed kitchen is a culinary enthusiast's dream, equipped with high-end appliances including a built-in range, microwave, and dishwasher, all seamlessly integrated for both functionality and style. The stacked washer and dryer add convenience, making laundry days a breeze. With two generously sized bedrooms and two and a half elegantly designed bathrooms, this home provides ample space for relaxation and rejuvenation. Each bathroom boasts modern fixtures and finishes, ensuring a spa-like experience at home. The attic space while unfinished, has the ability to be finished for additional living space, if desired. The exterior of the property is equally captivating, featuring beautifully maintained sidewalks and exterior lighting that enhances the home's curb appeal. Enjoy serene evenings on the private patio, where you can unwind and soak in the tranquil surroundings. The lot, spanning 1,330 square feet, offers a manageable outdoor space that complements the busy lifestyle of today's homeowner. Located in a vibrant community, this residence is not just a home; it's a lifestyle. The Chestertown Historic District is renowned for its rich history and picturesque streets, providing a unique backdrop for your daily life. Enjoy leisurely strolls through charming neighborhoods, explore local boutiques, or indulge in the culinary delights of nearby restaurants. This property is more than just a dwelling; it's an opportunity to embrace a luxurious lifestyle in a historic setting. With its impeccable condition and high-end features, this home is ready to welcome you into a world of comfort and elegance. Don't miss your chance to own a piece of this exclusive community-schedule your private tour today and experience the allure of this remarkable residence for yourself.

111 Kent St S, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

105 High St, Chestertown
$1,195,000
5 Beds ⋅ 5 Baths
Morning light pours through restored original windows. The river shimmers a block away, and a mansard roof that has watched over High Street since 1863 frames it all. Rebuilt after the fire of its day, the Tilley Residence has been brought back since 2022 by a top builder and his designer sister. A grand staircase, refinished by hand over many months, rises past glimpses of the water. The new custom kitchen is made for gathering. Upstairs, the primary suite has its own fireplace, and there are 4.5 brand-new baths. Below, a bright lower level holds a wine cellar. Everything unseen is new, too: HVAC, electrical, plumbing, roof and insulation. Outside, there’s a private fenced yard, a remodeled garage, and the historic Custom House next door. Shops, galleries, dining and the marina are all a short stroll away. There is no better chance to drop your keys and create your legacy in Chestertown's Historic District.

105 High St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

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