Chesapeake Landing Homes for Sale

Welcome to Chesapeake Landing, a picturesque subdivision nestled in the charming town of Chestertown, Maryland. Located in Kent County, this serene community offers a perfect blend of natural beauty and modern living, making it an ideal place for families, retirees, and everyone in between.

Chesapeake Landing is renowned for its stunning waterfront views and lush landscapes, providing residents with a tranquil environment to call home. The subdivision features a variety of beautifully designed homes, each showcasing unique architectural styles and contemporary amenities. Whether you’re searching for a cozy cottage or a spacious family residence, you’ll find a diverse selection of homes for sale that cater to every lifestyle and budget.

Living in Chesapeake Landing means enjoying the best of both worlds: the peacefulness of suburban life and the vibrant culture of Chestertown. Explore the local shops, dine at delightful restaurants, or take a leisurely stroll along the Chester River. Outdoor enthusiasts will appreciate the nearby parks and recreational areas, perfect for hiking, fishing, and boating.

With its welcoming community spirit and convenient access to major highways, Chesapeake Landing is not just a place to live but a place to thrive. Experience the charm of Kent County and discover the perfect home in this idyllic subdivision. Don’t miss out on the opportunity to be part of this delightful community; explore the homes for sale in Chesapeake Landing today and take the first step towards your new life in this enchanting corner of Maryland!

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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