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 offers a unique blend of serene living and vibrant local culture, making it an ideal choice for families, retirees, and anyone seeking a tranquil lifestyle.

Chesapeake Landing is strategically located in Kent County, surrounded by the breathtaking landscapes of the Eastern Shore. Residents enjoy easy access to the stunning Chesapeake Bay, where outdoor enthusiasts can indulge in activities like kayaking, fishing, and sailing. The nearby parks and nature trails provide ample opportunities for hiking and birdwatching, ensuring that you stay connected to the beautiful natural surroundings.

The subdivision boasts a variety of well-designed homes, each reflecting the classic architectural charm that Maryland is known for. With spacious layouts and modern amenities, these residences cater to diverse lifestyles, offering comfort and convenience. The friendly neighborhood atmosphere fosters a sense of community, where neighbors become friends and gatherings are a regular delight.

Chesapeake Landing is also conveniently located near Chestertown's vibrant downtown, filled with local shops, restaurants, and cultural attractions. Enjoy a leisurely stroll along the waterfront, explore art galleries, or savor delicious cuisine at one of the many eateries. The annual events and festivals hosted in the area create a lively ambiance, allowing residents to immerse themselves in the rich history and culture of this beautiful region.

Whether you are looking for a peaceful retreat or an active lifestyle, Chesapeake Landing is the perfect place to call home. Discover the charm of Chestertown and the warmth of this welcoming community 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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Joseph Ciganek

As an Eastern Shore Realtor, I know that a real estate transaction is built on trust. I pride myself on my honesty and integrity in providing the highest quality representation for my clients. I have spent my entire life in Chestertown and on the Chesapeake Bay and have a deep respect and understanding for why life here is so special. You can rely on my deep knowledge of the eastern shore and its waterways when buying a home. As an Eastern Shore native, full-time Realtor and licensed Attorney, I have the skill set to help you navigate any real estate transaction; waterfront, farms, commercial, you name it. Buying or selling real estate requires an experienced and trustworthy advocate. Let me be your guide. Growing up on the banks of the Chester River, I was fortunate enough to enjoy everything the Chesapeake Bay has to offer, whether crabbing, fishing or just about every water-sport you can think of. After graduating from Washington College with a B.A. in Economics and Finance, I attended University of Baltimore School of Law. Working full time and going to school at night, I graduated cum laude and proceeded to clerk for the Honorable Harris P. Murphy, Circuit Court of Kent County, Md. That’s when I decided to make a drastic career shift to practicing full time as a Realtor in 2021. Since then I have enjoyed showing others why life on the shore really is the land of pleasant living. Outside of real estate, I enjoy getting exercise with my black lab, playing pickleball, soccer and racing the historic log canoe sail boats up and down the Chesapeake Bay.

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