Chestertown Homes with Common Grounds Lot Description

Chestertown Homes with Common Grounds Lot Description

Welcome to Chestertown, Maryland—a hidden gem nestled in the heart of Kent County. This charming town, steeped in rich history and vibrant culture, offers a delightful blend of small-town charm and modern conveniences. With its picturesque streets lined with beautifully preserved 18th-century architecture, Chestertown invites you to explore its unique shops, artisanal eateries, and lively art scene. The town is also home to Washington College, which adds a youthful energy and a variety of cultural events throughout the year.

For those seeking a home in this enchanting locale, consider the inviting properties with common grounds. These homes not only provide comfortable living spaces but also foster a sense of community. Imagine stepping out of your front door to lush green spaces where neighbors gather, children play, and friendships blossom. The common grounds create a perfect backdrop for weekend picnics, morning jogs, or simply relaxing under the shade of a tree with a good book.

Living in Chestertown means you’ll enjoy the best of both worlds—peaceful suburban life while being just a stone’s throw away from the Chesapeake Bay. Whether you’re an outdoor enthusiast eager to explore the nearby nature trails or someone who appreciates the local arts and history, Chestertown has something for everyone.

Explore the possibilities of calling Chestertown home, where a vibrant community and beautiful surroundings await you. Your dream home with common grounds is not just a property; it’s a lifestyle waiting to be embraced. Come and discover the charm of Chestertown today!

Newest Chestertown Homes with Common Grounds Lot Description

3 Beds ⋅ 3 Baths

Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renovated in 2020, this home offers the perfect combination of timeless design, modern updates, and comfortable living. Hickory flooring flows throughout the main living areas and bedrooms, while LVP flooring provides durability and easy maintenance in all bathrooms and the laundry room. The heart of the home is the impressive gourmet kitchen, featuring quartz countertops, a granite-topped island, 5-burner propane range, double wall ovens, built-in microwave, pot filler, farmhouse sink, beautiful backsplash, and abundant cabinetry for exceptional storage. Open to the spacious great room, the kitchen creates an inviting gathering space highlighted by a propane fireplace with a beautiful mantel. The living room features Anderson sliding glass doors that open to the deck, creating an easy connection between indoor and outdoor living. The spacious primary suite is a true retreat, featuring Anderson sliding glass doors leading directly to the deck, a walk-in closet, and an updated primary bath with double vanity and a large tiled shower enclosed by glass doors. The third bedroom offers clever versatility with a Murphy bed that maximizes the space while providing a comfortable guest room when needed. Step outside to enjoy the deck and partially fenced backyard, complete with a storage shed and peaceful views of the open common area behind the property. An attached two-car garage and paved driveway add convenience and functionality. Meticulously maintained and beautifully updated, this home offers a wonderful opportunity to enjoy turnkey living in a highly desirable Chestertown location, close to the town's shops, restaurants, waterfront, and amenities. Don't miss the opportunity to make this exceptional home your own!

1003 Twin Ct, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

3 Beds ⋅ 3 Baths

Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly positioned just minutes from historic downtown Chestertown, local schools, and the YMCA—blending everyday convenience with a welcoming community atmosphere. Enter through the ground floor, where a flexible bonus room and one-car garage offer endless possibilities for a home office, gym, or recreation space. The heart of the home sits on the main level, featuring a generous living room and an eat-in kitchen that opens to a private rear deck—the perfect spot to unwind and look out at the wooded backdrop. Upstairs, you will find three comfortable bedrooms, including a primary suite with a private bath, alongside a dedicated laundry area. Turn-key and low-maintenance, this property is a fantastic opportunity for first-time buyers, downsizers, and investors alike.

104 Acorn Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Unique opportunity to expand or start your business just minutes from the Eastern Shore thoroughfares of Routes 301 and 213 and also just outside of downtown Chestertown. The blend of infrastructure and zoning such as public sewer, Industrial zoning, tractor trailer access, railway abutting the business park and 3 phase electric throughout the building make this irresistible for a wide variety of businesses. Iconic Eastern Shore architect Peter Newlin designed the building with passive solar heating and cooling in mind as evidenced in the dynamic roof pitch. Radiant floor heating ensures that not only are your employees happy but your machines and materials are better protected as well. The layout allows for great separation of personnel, office tasks, and shop space. 3 Bathrooms, one with shower, allow for the staff to have their space of their own without sacrificing customer experience. Quality control, conference and storage rooms are thoughtfully planned out and spacious. The exterior provides ample parking for staff and customers separately while also designed for tractor trailor turnaround. Over 2 acres and extra sewer allotment allow for vision and future possibilities. Less than 2 hours from Philadelphia, Wilmington, Baltimore, and Washington DC. Opportunities like this don't come up often so jump in now for the growth of the Eastern Shore.

25416 Commerce Ln, Chestertown

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

2 Beds ⋅ 3 Baths

MOTIVATED SELLER - BRING OFFERS. Listing will be removed September 30 until Spring 2027. Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be converted into a 3rd bedroom. Off the den is the first-floor bedroom and full bath. Enjoy the summer breeze from the private back screened-in porch; recently upgraded with high-tech flex screens and a ceiling waterproofing; keeping the porch dry. The real action is found upstairs. The living room – anchored by an electric fireplace with stone surround – is complemented by the oversized second story deck; perfect for grilling or watching picturesque Chester River sunsets. The modern kitchen features new stainless-steel appliances, abundant cabinet space, granite countertops and a large island with breakfast bar. Plenty of space for formal or casual dining. The second floor is finished by an oversized primary bedroom with ensuite bath and large walk-in closet. Should one desire an elevator; there are two locations where one could be built into the existing design. Leave your worries aside as the condo association takes care of all exterior maintenance, yardwork, and repairs. Boaters will enjoy the well-maintained community dock with slips available for purchase or lease (with board approval), or just drop in a kayak or paddle board; great on warm summer evenings. Other community amenities include the pool, walking paths, garden, picnic and grilling areas, and a fire pit. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront walkways and parks. Chestertown is home to many festivals and an award-winning Farmer's Market every Saturday. New YMCA with full gym, racquet sports, lap pool, sauna, etc. Don’t miss your opportunity to enjoy worry-free living along the Chester River.

103 Landing Ln, 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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