Chestertown Homes with Circular Driveway Parking desc

Welcome to Chestertown, Maryland—a charming riverside town that perfectly blends history, culture, and natural beauty. Nestled in Kent County along the picturesque banks of the Chester River, Chestertown is renowned for its vibrant arts scene, quaint shops, and rich colonial heritage. Stroll through the historic downtown area, where you’ll find beautifully preserved 18th-century buildings, delightful cafes, and local galleries showcasing the work of talented artisans. The town also hosts a variety of events throughout the year, including the popular Chestertown Tea Party Festival, celebrating its storied past.

For those considering a home in this idyllic setting, you'll find a selection of properties featuring circular driveways—an elegant touch that enhances both convenience and curb appeal. Homes with circular driveway parking not only provide ample space for multiple vehicles but also offer a graceful entrance that welcomes guests with open arms. Imagine driving up to your dream home, surrounded by lush greenery and the charm of Chestertown’s historic charm.

Living in Chestertown means enjoying a close-knit community with access to scenic parks, recreational activities, and a variety of outdoor adventures. Whether you’re kayaking on the river, exploring the nearby Eastern Shore, or simply savoring the local cuisine, life in Chestertown is both peaceful and fulfilling. With its unique blend of history, culture, and stunning homes, including those with circular driveways, Chestertown is truly a gem waiting to be discovered. Come and experience the magic of this enchanting town!

Newest Chestertown Homes with Circular Driveway Parking desc

$468,000

3 Beds ⋅ 2 Baths

Charming Brick Rancher Near the Chester River This custom-built brick rancher sits in a nice Chestertown neighborhood with excellent curb appeal, a classic hipped roof, and a convenient circular driveway. The drive runs under a gable-roofed breezeway that connects to an oversized 26x40 two-car garage, which will soon have brand-new garage doors. Coming into the Home... Living Room: Walk along the cobblestone slate path and pass through the new, classic front door into a spacious living room featuring hardwood floors that run throughout the entire house. Dining & Kitchen: A curved archway leads from the living room directly into the dining room. The dining room has an entryway to the kitchen, which could easily be opened up for an even more open feel. Porch: The dining room leads right out to a comfortable porch—the perfect spot to relax and enjoy this nice, quiet neighborhood. Mudroom & Back Entry: An oversized back entry from the breezeway leads into a large mudroom and utility space. Featuring multiple closets and laundry hookups, this functional area offers plenty of space to be creative and fit your family's needs. Bedrooms: The main floor includes three bedrooms with hardwood floors and two full bathrooms Basement: The full basement features an open space with brand-new windows that allow plenty of natural light inside. It is equipped with a new sump pump, offering a perfect blank canvas for storage, a gym, or a rec room. Utilities, Key Updates & Location The house sits on a generous lot with mature landscaping and is connected to well water and public septic. Recent mechanical and structural updates include: Brand-new roof, oil furnace paired with a new HVAC system for efficient heating and cooling. Fresh paint inside and out. You can enjoy beautiful views of the Chester River coming and going from your new home, as well as scenic river views while taking your neighborhood walks. Enjoy the convenience of being just minutes from downtown shopping and dining. Bring your design ideas to update the interior and make it your own!

25750 Collins Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$1,450,000

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. 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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