Chesapeake Landing Real Estate

Chesapeake Landing Real Estate

Welcome to Chesapeake Landing, a picturesque subdivision nestled in the heart of Chestertown, Maryland. This charming community is a hidden gem in Kent County, offering a perfect blend of serene suburban living and vibrant local culture.

Chesapeake Landing is renowned for its stunning natural landscapes, characterized by lush greenery and scenic views that are sure to captivate any nature lover. Residents enjoy easy access to the tranquil waters of the Chesapeake Bay, making it an ideal spot for boating, fishing, and other water activities. The community is designed to foster a sense of belonging, with friendly neighbors and well-maintained common areas that encourage outdoor gatherings and leisurely strolls.

The subdivision features a variety of homes, each thoughtfully designed to cater to diverse lifestyles. Whether you’re searching for a cozy cottage or a spacious family home, Chesapeake Landing has something to suit your needs. Many properties boast modern amenities while retaining the charming architectural style that reflects the rich history of the area.

Living in Chesapeake Landing means being just a stone's throw away from Chestertown's vibrant downtown, where you can explore delightful shops, enjoy gourmet dining, and immerse yourself in the local arts scene. The community is also conveniently located near top-rated schools and recreational facilities, making it a perfect choice for families.

Experience the charm and tranquility of Chesapeake Landing, where every day feels like a vacation in this idyllic Maryland haven. Come and discover your dream home in this enchanting subdivision today!

Newest Listings in Chesapeake Landing

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

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

All offers considered! Investors- this lot could possibly have public utilities available in the future! Currently a recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not currently buildable.

Kinglet Rd, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Spinnaker Rd, Chestertown

Listing courtesy of Paul Wesley Real Estate. Contact: 7032822709

Great opportunity to own a lot in Chesapeake Landing! Currently does not have a valid perc. Water access to Worton Creek if you join the voluntary civic association! Close to Worton Marina and Chestertown.

Sheldrake Dr, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

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