Chestertown Homes with No Thru Street Lot features

Welcome to Chestertown, Maryland—a hidden gem nestled in the heart of Kent County, where historic charm meets modern living. This picturesque town, situated along the banks of the Chester River, boasts a rich colonial history that is beautifully reflected in its well-preserved architecture and vibrant downtown area. With its quaint shops, delightful restaurants, and an array of cultural events, Chestertown offers a unique blend of small-town warmth and community spirit.

One of the most appealing features of homes in Chestertown is the availability of properties on no-thru streets. These serene lots provide a peaceful retreat from the hustle and bustle of everyday life, allowing residents to enjoy a tranquil environment while still being conveniently located near the town's amenities. Imagine stepping outside your front door to a quiet street, where children can play freely and neighbors become friends. Homes on no-thru streets often come with larger yards and a sense of privacy, making them perfect for families or anyone seeking a little extra space.

In Chestertown, you’ll find a diverse array of architectural styles, from charming historic homes to modern constructions, all set against a backdrop of natural beauty. With its close-knit community, excellent schools, and a variety of recreational opportunities, Chestertown is not just a place to live—it's a lifestyle. Whether you're drawn to the allure of its rich history or the appeal of a peaceful neighborhood, Chestertown is ready to welcome you home. Explore the possibilities today and discover the perfect no-thru street lot that fits your dreams!

Newest Chestertown Homes with No Thru Street 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