Chesapeake Landing Homes for Sale

Welcome to Chesapeake Landing, a hidden gem nestled in the picturesque town of Chestertown, Maryland. This charming subdivision is a perfect blend of serene living and vibrant community life, making it an ideal choice for families, retirees, and anyone looking to embrace the beauty of the Eastern Shore.

Chesapeake Landing is characterized by its stunning landscapes, featuring lush greenery and scenic views that capture the essence of Maryland’s natural beauty. The community is designed with a focus on comfort and convenience, offering a variety of well-appointed homes that cater to diverse lifestyles. From cozy single-family residences to spacious modern designs, there’s something for everyone in this delightful neighborhood.

For those seeking homes for sale, Chesapeake Landing boasts a selection that is sure to impress. Each property is thoughtfully constructed, featuring high-quality finishes and contemporary amenities. Residents can enjoy open floor plans, gourmet kitchens, and inviting outdoor spaces perfect for entertaining or simply unwinding after a long day. With a strong sense of community, neighbors often come together for local events and gatherings, fostering lasting friendships and a welcoming atmosphere.

Living in Chesapeake Landing means you’re just a stone's throw away from the historic charm of Chestertown, where you can explore quaint shops, delightful eateries, and cultural attractions. Additionally, the proximity to the Chesapeake Bay offers endless opportunities for outdoor activities, from boating and fishing to leisurely strolls along the waterfront.

Discover your dream home in Chesapeake Landing today, where comfort meets community in the heart of Kent County!

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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