Chestertown Homes with Circular Driveway Parking features

Welcome to Chestertown, Maryland—a hidden gem nestled in the heart of Kent County. This picturesque town is steeped in rich history and charm, making it an enchanting place to call home. With its vibrant arts scene, delightful waterfront views along the Chester River, and a community that thrives on its local culture, Chestertown offers a unique blend of small-town warmth and artistic flair.

One of the standout features of many homes in this area is the coveted circular driveway. Imagine coming home to a property where convenience meets elegance! Homes with circular driveways not only provide ample parking for family and guests but also add a touch of sophistication and curb appeal. These thoughtfully designed entrances create a welcoming atmosphere and make it easy to navigate in and out of your driveway, especially during those busy family gatherings or social events.

Chestertown is known for its historic architecture, charming boutiques, and a plethora of outdoor activities. Whether you’re strolling along the quaint streets, enjoying a meal at one of the local eateries, or taking part in the annual Chestertown Tea Party Festival, there’s always something to enjoy. With a strong sense of community and a rich tapestry of experiences, Chestertown is more than just a place to live; it’s a lifestyle.

If you’re searching for a home that combines modern conveniences with a touch of classic charm, look no further. Explore the delightful properties in Chestertown with circular driveways, and discover your perfect sanctuary in this idyllic Maryland town!

Newest Chestertown Homes with Circular Driveway Parking features

$2,895,000

5 Beds ⋅ 4 Baths

Discover 6324 Quaker Neck Road, an exceptional waterfront estate spanning over 5 acres along the East Fork of Langford Creek offering over 5 feet of water at low tide. Over 5,900 square feet of refined living space with 5 bedrooms and 4 baths, designed for elegant Shore entertaining and everyday ease. A new private pier with swim platform and boat lift, plus your private beach, extends living outdoors — complemented by a detached garage with carriage house and a pole building. Minutes to Chestertown, yet quietly removed — a distinguished Quaker Neck offering for the buyer who wants it all.

6324 Quaker Neck Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

$1,375,000

4 Beds ⋅ 5 Baths

Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away. The home features 4 bedrooms and 5 full bathrooms, plus a large loft that could be used as an additional bedroom. The large eat-in kitchen has expansive windows that perfectly frame the water view. A great spot for entertaining! Doors in the kitchen lead to the waterfront deck, spanning the front of the home. A new roof was installed in June, 2026. In both sitting rooms, you’ll find fireplaces that have been conveniently updated to propane. The first-floor primary bedroom opens up to the waterfront deck and offers a fantastic water view, as well as a large bathroom that was recently updated. Upstairs you’ll find two waterfront bedrooms, one with an updated attached bath. There's a second full bathroom and ample closet space in the hallway. Downstairs, there are two additional full bathrooms and a large bedroom. Above the kitchen sits the light-filled loft, a great office, studio, or extra bedroom. The exterior has a generous front porch, outdoor shower, circular drive, 2-car garage, fenced dog run, and additional garage space connected to the basement. This light-filled waterfront property is located 15 minutes away from the waterfront community of Rock Hall and historic Chestertown.

22470 Fairgale Farm Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

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