Chestertown Historic District Real Estate

Chestertown Historic District Real Estate

Welcome to the Chestertown Historic District, a charming gem nestled in the heart of Maryland’s picturesque Kent County. This captivating area is not just a neighborhood; it’s a vibrant tapestry of history, culture, and community. With its roots tracing back to the 18th century, Chestertown boasts a rich heritage that is beautifully preserved in its stunning architecture and cobblestone streets.

As you stroll through the Historic District, you’ll be greeted by an array of well-preserved colonial and Victorian homes, each with its own unique story to tell. The district is recognized for its commitment to maintaining its historical integrity, making it a delightful place for history enthusiasts and families alike. The iconic Chestertown Tea Party Festival, celebrating the town’s revolutionary spirit, is a must-see event that brings the community together every spring.

Nature lovers will appreciate the proximity to the Chester River, where you can enjoy scenic views, boating, and fishing. The district is also home to a variety of local shops, art galleries, and restaurants, offering everything from unique artisanal goods to delectable dining experiences.

Living in the Chestertown Historic District means embracing a lifestyle that values community and connection. The friendly neighbors and active civic organizations foster a warm and welcoming atmosphere. Whether you’re looking for a quaint retreat or a vibrant place to raise a family, the Chestertown Historic District offers an unparalleled blend of history, charm, and modern living. Discover your new home in this enchanting community today!

Newest Listings in Chestertown Historic District

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 N Water St Unit 3, Chestertown
$459,000
2 Beds ⋅ 2 Baths
Second story, waterfront condo in historic Chestertown. Comes with a private boat slip at the end of the dock. 2 bedrooms and 2 full baths. Spacious patio with a stunning view of the Chester River. One of the most coveted streets in historic Chestertown!

105 N Water St Unit 3, Chestertown

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

226 S Water St, Chestertown
$898,000
3 Beds ⋅ 4 Baths
Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. You'll love the warm hardwood floors throughout the home. On the second level you'll find two bedrooms and two bathrooms. The third bedroom encompasses the entire third floor and has a great view of the Chester River. You'll enjoy the large back balcony with views of historic Chestertown. The third level could be used as the primary bedroom; there is a large full bathroom and closet. The townhomes have a private driveway, so you'll never worry about finding a parking space. Take advantage of the easy access to Wilmer Park and Chestertown Marina, located just across the street. This townhouse is located in the heart of all Chestertown has to offer! Just a short distance to shops, restaurants, renowned bakeries, and the year-round farmers market by Fountain Park. You will have a front-row seat to the Downrigging Festival! Not to mention the many festivals held in downtown Chestertown throughout the year.

226 S Water St, Chestertown

Listing courtesy of Gunther-McClary Real Estate. 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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