Chestertown Homes with Paved Parking features

Welcome to Chestertown, Maryland—a charming town steeped in history and surrounded by the natural beauty of the Eastern Shore. Nestled along the banks of the Chester River, Chestertown is known for its picturesque waterfront, vibrant arts scene, and a strong sense of community. With a population that embraces both tradition and modernity, this quaint town offers residents a serene lifestyle paired with the conveniences of contemporary living.

One of the most appealing aspects of Chestertown is its array of homes, many of which feature paved parking—an essential convenience for today’s homeowners. Imagine coming home to a beautifully maintained property with easy access to your vehicle, all while enjoying the scenic views of your neighborhood. The paved parking not only enhances the aesthetic appeal of your home but also provides a practical solution to the often-chaotic task of finding parking.

In Chestertown, you’ll find a diverse selection of homes, from historic colonial houses to modern builds, all designed to cater to your lifestyle needs. The town’s commitment to preserving its heritage while fostering growth means that whether you’re looking for a cozy cottage or a spacious family home, you’ll find a perfect fit here.

Explore the local shops, dine in delightful restaurants, and immerse yourself in community events that reflect the town’s rich culture. Chestertown is more than just a place to live; it’s a vibrant community waiting to welcome you home. Experience the charm of Chestertown, where history meets modern living, and paved parking is just one of the many features that make this town a wonderful place to call home.

Newest Chestertown Homes with Paved Parking features

$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:

$795,000

Commercial Development Site on busy MD Rte 213, Prime location across from new Starbucks and Washington College Campus. Approx 1 acre, zoned C-3. Suitable for retail, restaurant, service uses. Water and sewer available.

515 Washington Ave, Chestertown

Listing courtesy of EShore. Contact:

Start Your Search