Chestertown Homes with Other Style

Chestertown Homes with Other Style

Welcome to Chestertown, Maryland—a hidden gem nestled along the banks of the Chester River. With its rich history, vibrant arts scene, and picturesque waterfront, Chestertown offers a unique blend of small-town charm and modern amenities, making it an ideal place to call home.

Founded in the 1700s, Chestertown is steeped in history, with beautifully preserved colonial architecture that tells the story of its past. Stroll through the quaint streets lined with historic homes, art galleries, and boutique shops, where you can discover local artisans and craftspeople showcasing their talents. The town hosts a variety of cultural events throughout the year, including the renowned Chestertown Tea Party Festival, which celebrates its revolutionary roots and brings the community together in a spirit of fun and festivity.

For outdoor enthusiasts, Chestertown is a paradise. Enjoy kayaking or paddleboarding on the serene waters of the Chester River, or take a leisurely bike ride along the scenic trails that wind through the surrounding countryside. The nearby Eastern Shore is also home to beautiful parks and wildlife refuges, perfect for hiking and birdwatching.

When it comes to real estate, Chestertown offers a diverse array of homes that cater to various tastes and lifestyles. From charming historic residences with character to contemporary homes that embrace modern design, there’s something for everyone. Whether you’re seeking a cozy cottage or a spacious family home, Chestertown’s real estate market is sure to impress.

Experience the warmth and community spirit of Chestertown, where every day feels like a getaway. Come explore the possibilities and find your dream home in this enchanting riverside town!

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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