Chestertown Homes with Cul-De-Sac Lot Description

Welcome to Chestertown, Maryland—a charming town that beautifully blends rich history with modern living. Nestled in Kent County along the picturesque banks of the Chester River, Chestertown is renowned for its vibrant arts scene, historic architecture, and a strong sense of community. With a population of just over 5,000, this quaint town offers a peaceful escape from the hustle and bustle of city life, while still providing access to a variety of amenities and recreational activities.

One of the most appealing aspects of Chestertown is its commitment to preserving its historical roots. Stroll through the tree-lined streets and marvel at the well-preserved colonial buildings, or visit the local galleries and boutiques that showcase the work of talented artisans. The annual Chestertown Tea Party Festival and the renowned Washington College add to the town's lively atmosphere, making it a hub for culture and community engagement.

For those seeking a family-friendly environment, homes with cul-de-sac lots in Chestertown are an ideal choice. These properties offer a unique blend of tranquility and safety, perfect for children to play freely while parents enjoy peace of mind. With reduced traffic and a welcoming neighborhood feel, cul-de-sac living fosters a strong sense of community. Spacious yards and proximity to parks create the perfect backdrop for family gatherings and outdoor activities.

In Chestertown, you'll find not just a home, but a lifestyle enriched with history, community spirit, and the beauty of nature. Whether you're drawn by the charming homes or the vibrant local culture, Chestertown is waiting to welcome you home.

Newest Chestertown Homes with Cul-De-Sac Lot Description

$499,900

3 Beds ⋅ 3 Baths

Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renovated in 2020, this home offers the perfect combination of timeless design, modern updates, and comfortable living. Hickory flooring flows throughout the main living areas and bedrooms, while LVP flooring provides durability and easy maintenance in all bathrooms and the laundry room. The heart of the home is the impressive gourmet kitchen, featuring quartz countertops, a granite-topped island, 5-burner propane range, double wall ovens, built-in microwave, pot filler, farmhouse sink, beautiful backsplash, and abundant cabinetry for exceptional storage. Open to the spacious great room, the kitchen creates an inviting gathering space highlighted by a propane fireplace with a beautiful mantel. The living room features Anderson sliding glass doors that open to the deck, creating an easy connection between indoor and outdoor living. The spacious primary suite is a true retreat, featuring Anderson sliding glass doors leading directly to the deck, a walk-in closet, and an updated primary bath with double vanity and a large tiled shower enclosed by glass doors. The third bedroom offers clever versatility with a Murphy bed that maximizes the space while providing a comfortable guest room when needed. Step outside to enjoy the deck and partially fenced backyard, complete with a storage shed and peaceful views of the open common area behind the property. An attached two-car garage and paved driveway add convenience and functionality. Meticulously maintained and beautifully updated, this home offers a wonderful opportunity to enjoy turnkey living in a highly desirable Chestertown location, close to the town's shops, restaurants, waterfront, and amenities. Don't miss the opportunity to make this exceptional home your own!

1003 Twin Ct, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

$750,000

3 Beds ⋅ 3 Baths

Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A freshly sealed asphalt drive curves to a welcoming front entry, where a classic brick facade sets a warm, distinctive tone. A two-car attached garage provides direct entry and everyday convenience. * Inside, the open kitchen—complete with breakfast area—flows seamlessly into a spacious family room, perfect for everyday living. A separate dining room makes entertaining easy. The family room is an elegant space for gatherings, while a dedicated sunroom and screened-in porch invite you to enjoy the serene, park-like backyard in every season. The large deck offers an additional outdoor retreat with tranquil wooded views. * The generous primary suite features an en-suite bath, while two additional bedrooms makes for flexible bedroom accommodations for family, guests, or a quiet work-from-home office space. A convenient half bath and main-floor laundry round out the practical layout. A full basement offers abundant storage and endless potential for an artist’s studio, workshop, recreation room, or finished expansion. * With its pristine landscaping, mature plantings, and verdant views, this exceptional home is a rare find. And the location is second to none—just minutes from historic downtown Chestertown. Stroll tree-lined streets to discover specialty shops, art galleries, restaurants, and the Saturday Farmers Market at Fountain Park. Washington College, the nation’s tenth-oldest college, anchors the community with year-round cultural events, lectures, and performances. Outdoor enthusiasts will love the nearby Rail Trail, Sultana Lawrence Wetlands Preserve, marinas, and public boat launches providing easy access to the Chester River and Chesapeake Bay. First Friday celebrations, waterfront festivals, and a vibrant arts scene make Chestertown one of the Eastern Shore’s most beloved places to call home.

216 Birch Run Rd, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

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