Chestertown Homes with Vegetation Planting Lot features

Welcome to Chestertown, a charming gem nestled in the heart of Queen Anne's County, Maryland. This picturesque town, located along the banks of the Chester River, is steeped in rich history and vibrant culture, making it an ideal place to call home. With its quaint streets lined with historic buildings, Chestertown exudes a warmth that invites you to explore its local shops, art galleries, and delightful eateries. The town is also known for its lively community events, including the renowned Chestertown Tea Party Festival, which celebrates its colonial heritage.

For those seeking a home that harmonizes with nature, Chestertown offers an array of properties featuring lush vegetation planting lots. These homes are designed to blend seamlessly with the natural beauty of the area, providing residents with serene outdoor spaces that promote relaxation and tranquility. Imagine sipping your morning coffee surrounded by vibrant flower beds, mature trees, and the soothing sounds of nature. Whether you’re an avid gardener or simply appreciate the beauty of well-maintained landscapes, these homes provide the perfect backdrop for outdoor living.

Chestertown is not just a place to live; it’s a lifestyle that embraces community, nature, and history. With its close-knit atmosphere and easy access to outdoor activities like boating, fishing, and hiking, you’ll find that every day offers a new adventure. Explore the possibility of making Chestertown your new home, where the charm of small-town living meets the beauty of nature at your doorstep. Come discover the perfect blend of comfort, community, and natural splendor in this enchanting Maryland town!

Newest Chestertown Homes with Vegetation Planting Lot features

$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: 4106733344

$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:

Start Your Search