Chesapeake Landing Homes for Sale

Welcome to Chesapeake Landing, an enchanting subdivision nestled in the heart of Chestertown, Maryland. This picturesque community offers a unique blend of natural beauty and modern living, making it an ideal choice for families, retirees, and anyone seeking a serene lifestyle in the charming Kent County.

Chesapeake Landing is renowned for its stunning waterfront views, lush landscapes, and friendly atmosphere. With easy access to the tranquil waters of the Chesapeake Bay, residents can indulge in a variety of outdoor activities, from kayaking and fishing to leisurely strolls along scenic trails. The subdivision’s proximity to Chestertown’s historic downtown area means that you can enjoy quaint shops, delightful restaurants, and vibrant community events just moments from your doorstep.

Homes for sale in Chesapeake Landing reflect the area’s commitment to quality living. Each property features thoughtful designs, spacious layouts, and modern amenities that cater to today’s lifestyle. Whether you’re looking for a cozy cottage or a larger family home, you’ll find a diverse selection of residences that suit your needs. Many homes come equipped with beautiful outdoor spaces, perfect for entertaining or simply relaxing while enjoying the picturesque surroundings.

Living in Chesapeake Landing means embracing a lifestyle of tranquility and connection to nature, all while being part of a welcoming community. Don’t miss your chance to find your dream home in this idyllic subdivision—explore the available listings today and discover the beauty of Chesapeake Landing for yourself!

Newest Chesapeake Landing Homes for Sale

$335,000

3 Beds ⋅ 2 Baths

Welcome to 10720 Foreston Rd, a charming and inviting home situated in the peaceful surroundings of Chesapeake Landing in Chestertown, MD. 3 bedrooms and 2 full bathrooms with a spacious eat-in kitchen and generous living room provides ample room for comfortable living. Move-in ready condition. Inside, you'll immediately notice the warmth and character of the stunning hardwood floors that flow throughout the home. The open and airy layout ensures a seamless flow between the living spaces, making it perfect for entertaining or just relaxing at home. The well-equipped laundry area comes complete with both a washer and dryer for added convenience. Take full advantage of the outdoor amenities this property has to offer. Start your mornings with coffee on the cozy screened porch or wind down your evenings on the expansive deck overlooking the fenced yard. There's plenty of space to garden, play, or simply enjoy the outdoors in privacy. The property also includes a garage, providing extra storage space and parking. This home is ideal for those seeking both charm and functionality in a serene setting. Don't miss the opportunity to call 10720 Foreston Rd your new home. Schedule your showing today to experience all that this property has to offer!

10720 Foreston Rd, Chestertown

Listing courtesy of Compass. Contact: (301) 298-1001

$429,900

4 Beds ⋅ 3 Baths

Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country kitchen with new appliances, new counters, and plenty of space for gathering. A main-level bedroom adds flexibility for guests or one-level living. Enjoy morning coffee or evening sunsets on the back deck overlooking the open, cleared 0.39-acre lot—perfect for gardening or outdoor fun. Additional highlights include a 2-car garage and access to community amenities with a beach, fishing pier, and pavilion. Just minutes from historic downtown Chestertown, you’ll love being close to local shops, dining, marinas, and all the charm of Eastern Shore living.

10781 Fermoy Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

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