Chestertown Historic District Homes with Water View

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

As you stroll through the tree-lined streets of the Chestertown Historic District, you'll be captivated by the beautifully preserved 18th and 19th-century homes, each telling a story of the town's storied past. The district is listed on the National Register of Historic Places, ensuring that its character and heritage are preserved for generations to come. Here, history enthusiasts will find themselves in paradise, with landmarks like the iconic Chester River and the charming Washington College adding to the area's allure.

For those seeking a tranquil lifestyle with stunning water views, the Chestertown Historic District offers an array of homes that overlook the serene Chester River. Imagine waking up to the gentle sounds of the water lapping against the shore, with breathtaking sunrises painting the sky in vibrant hues. These waterfront properties not only provide a picturesque backdrop for your daily life but also create an inviting atmosphere for entertaining friends and family.

With its vibrant arts scene, delightful shops, and a variety of local dining options, the Chestertown Historic District is more than just a place to live—it's a community where neighbors become friends and every day feels like a vacation. Experience the charm of Chestertown, where history meets modern living, and find your dream home with a view today!

Newest Chestertown Historic District Homes with Water View

$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:

$1,245,500

5 Beds ⋅ 5 Baths

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the waterfront promenade or to morning coffee at Evergrain, the location captures the rhythm of Chestertown living—laid back yet polished, historic yet vibrant. This is more than a home; it is an irreplaceable asset and a true legacy property within one of Maryland’s most beloved waterfront towns.

105 High St, Chestertown

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

Start Your Search