Chestertown Homes with Other Style

Chestertown Homes with Other Style

Welcome to Chestertown, Maryland—a hidden gem nestled in the heart of Queen Anne's County. This charming town, steeped in history and brimming with character, offers a unique blend of small-town charm and vibrant community life. Founded in the 18th century, Chestertown is a picturesque waterfront community located along the beautiful Chester River, making it a haven for boating enthusiasts and nature lovers alike.

As you stroll through the tree-lined streets, you'll be captivated by the well-preserved colonial architecture, delightful boutiques, and inviting cafes. The town is home to a rich cultural scene, with art galleries, theaters, and annual festivals that celebrate its heritage and community spirit. The renowned Washington College, located in the heart of Chestertown, adds to the town's intellectual vibrancy and provides a variety of events and lectures for residents and visitors alike.

When it comes to real estate, Chestertown offers an array of homes that cater to diverse tastes and lifestyles. From charming historic homes with character to modern residences that blend seamlessly into the landscape, there’s something for everyone. Whether you’re searching for a cozy cottage, a spacious family home, or a stylish waterfront property, Chestertown has it all. The town’s real estate market showcases a variety of architectural styles, ensuring that you’ll find the perfect place to call home.

Embrace the beauty and warmth of Chestertown, where every street tells a story, and every home is an invitation to create new memories. Come discover why this enchanting town is the ideal place to settle down and enjoy life at a leisurely pace.

Newest Chestertown Homes with Other Style

3 Beds ⋅ 2 Baths

Affordable opportunity in the heart of downtown Chestertown! This 3-bedroom, 1.5-bath townhome is ideally located just minutes from Washington College, shops, restaurants, parks, and the waterfront. Offering a functional floor plan with spacious living areas, generously sized bedrooms, and a back yard with additional rear parking, this home is ready for its next owner to make it their own. This property presents an excellent opportunity for first-time homebuyers looking to build equity or investors seeking their next investment property! Opportunities at this price point in Chestertown don't come along often! Schedule your showing today and discover the potential this home has to offer! Property is being sold AS-IS.

409 Calvert St, Chestertown

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

Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.

201 N Lynchburg St, Chestertown

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800

3 Beds ⋅ 3 Baths

Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 square feet of living space with 3 bedrooms and 2.5 baths. On everyone's wish list is the generous sized 2-car garage with extra side entrance. The first floor features an open and functional layout designed for everyday living. The kitchen is open to the breakfast area and living room, creating a cohesive main living area. The living room includes a built-in fireplace, while a formal dining room sits just off the kitchen. The kitchen features granite countertops and tile flooring, which continues through the pantry and mudroom. All other countertops throughout the home are upgraded. A spacious laundry room and pantry are conveniently located off the kitchen. The first floor also includes a powder room and a first-floor extra room ideal for a home office or study. A spacious entryway from the attached two-car garage or additional side entrance provides a practical everyday entry. The first-floor primary suite offers comfortable main-level living and includes cathedral ceilings, a private door leading to a roomy composite back deck, and an attached bathroom with marble heated flooring and a walk-in shower, along with a spacious walk-in closet. Upstairs, the home offers two bedrooms with a loft area in between , providing flexible additional living space. Custom inlay flooring is featured in the formal dining room, living room, foyer, primary suite and first-floor extra room, tastefully alternating wood types and adding subtle character. Overall, this home offers quality construction, thoughtful design, and a layout that works well for everyday living. Still more details and touches to be seen when you come to visit. This home truly is move in ready.

204 Double Creek Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. 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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