Homes with a View for Sale in Chestertown, MD

Home with View for sale in Chestertown, MD:

Tucked away along the quiet shores of Still Pond Creek, this cedar cabin offers a rare blend of privacy, comfort, and natural beauty. Surrounded by mature woods and set on a peaceful stretch of waterfront, this 1,944 square foot home features 3 bedrooms, 2 bathrooms, a spacious screened-in porch perfect for crab feasts, and a private pier with 2'+ MLW ideal for boating, kayaking, crabbing, and fishing. Whether you’re seeking a weekend retreat or a year-round escape, this property captures the essence of Eastern Shore living—simple, timeless, and immersed in nature where mind, body, and soul find balance.

Home with View for sale in Chestertown, MD:

Welcome to Silly Manor, a Chesapeake Bay-front property with an abundance of coastal charm and panoramic views. This home is perfectly situated on the coveted Lawton Avenue, one of Kent County's most sought-after neighborhoods. Enjoy stunning sunsets all year-round and direct access to the dynamic waters of the Chesapeake Bay. The open living and dining space offer spectacular views of the Chesapeake. The kitchen opens up to the patio and garden, and has a spacious island for entertaining. The home was designed with a first-floor primary suite, offering convenient (and hard-to-find) one-floor living. There are two additional bedrooms and a full bath on the second floor. Watch the boats glid

Home with View for sale in Chestertown, MD:

Welcome to 530 Kennersley Farm Lane, nestled in the private waterfront community of Kennersley Farm. Set on 5 private acres along Island Creek, this property offers lots of privacy and nature. A long, tree-lined driveway leads you past mature landscaping and ample parking, where you can see views of the water. Inside, there is beautiful flooring and a bright, open layout. The kitchen features granite countertops, a center island, upgraded GE Profile appliances, and an eat-in area overlooking the in-ground pool and Island Creek. The primary suite, located on the first floor, is a true retreat with a huge walk-in closet, featuring a soaking tub, dual granite vanity, and tile shower. This roo

Home with View for sale in Chestertown, MD:

Welcome to this beautifully updated 5-bedroom, 3.5-bath home nestled in the desirable community of Church Hill. Designed for comfort and style, this spacious residence offers the perfect balance of modern updates and peaceful Eastern Shore living. Step inside to find a bright and inviting interior featuring brand-new luxury vinyl plank flooring on the main level and new carpet upstairs. The entire home has been freshly painted, giving it a crisp, move-in-ready feel. The gourmet kitchen is a true showpiece — complete with new stainless steel appliances, a large center island, and ample cabinet and counter space, perfect for gatherings and meal prep alike. Enjoy two primary suites, one

Home with View for sale in Chestertown, MD:

Originally built with handcrafted bricks in 1782, this Flemish Bond Georgian Colonial home is the embodiment of simple elegance. Restored with the utmost historical respect in the mid-1980’s with handcrafted oak windows and mahogany doors with period hardware and modernized with preservation-sensitive practices and materials over the past eight years by the current stewards of the home, step into the past while enjoying today’s comforts. The four-bay home has a traditional floor plan with the living and dining room flanking the center hall, a large sunken family room anchored by the massive hearth – reconstructed with original bricks from the 1782 structure and walnut mant

Home with View for sale in Chestertown, MD:

Welcome to 12765 Still Pond Road on Maryland’s Eastern Shore. This 2,000+ sq ft Colonial sits on a landscaped lot with pastoral views and offers incredible rehab potential. Just 3 miles from Betterton Beach, 10 minutes to historic downtown Chestertown, and 15 miles to the harbor town of Rock Hall, the location provides easy access to waterfront recreation, dining, and shopping. The home features 3 spacious bedrooms and a full bath upstairs, plus a main-level den with adjacent full bath that could serve as a first-floor primary suite or home office. Vintage details throughout include original trim, built-ins, and classic hardware. A bright kitchen opens to a large laundry/utility room