Chestertown Homes with Street View

Chestertown Homes with Street View

Welcome to Chestertown, Maryland – a charming riverside town that beautifully blends rich history with vibrant community life. Nestled along the banks of the Chester River, Chestertown is known for its picturesque streets, historic architecture, and a warm, welcoming atmosphere that makes it a perfect place to call home.

As you stroll through the quaint downtown area, you'll be captivated by the unique boutiques, art galleries, and delightful eateries that line the streets. The town's historic charm is evident in its well-preserved buildings, many of which date back to the 18th century. Notably, Chestertown is home to Washington College, which adds a youthful energy and a variety of cultural events to the community calendar.

For those seeking a home in this idyllic setting, Chestertown offers a diverse range of real estate options. From charming colonial-style houses to modern waterfront properties, there’s something for every taste and lifestyle. Many homes feature beautiful gardens and scenic views, allowing residents to enjoy the natural beauty that surrounds them.

One of the best ways to explore the available properties is through our interactive Street View feature. This tool allows you to virtually walk through the neighborhoods, getting a true sense of the community and the charm of each home. Imagine sipping your morning coffee while gazing at the serene river views or enjoying a leisurely stroll down tree-lined streets.

Whether you're drawn to Chestertown for its historical significance, vibrant community spirit, or stunning waterfront, you’ll find that this hidden gem in Maryland offers a truly unique living experience. Come discover your dream home in Chestertown today!

Newest Chestertown Homes with Street View

Vacant lot ready for your own choice of residence. Walking distance to the Chester River community access by boat or just enjoy the waterfront on the community deck.

233 Merganser Dr, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Mixed-use commercial property in charming historic Chestertown. 327 Cannon was newly constructed in 2006, yet is perfectly situated in bustling historic district. Offering historic charm without the extra maintenance. The building contains two large units with many possibilities. The first level is outfitted with a commercial kitchen and large dining space overlooking Cannon St. Over 1300 sq ft of professional kitchen space, an office, and dining area. The space has many possibilities for a restaurant or other commercial business in the future. Currently, this unit is leased to Occasions Catering. The upstairs apartment is inviting and spacious, offering two bedrooms each with an ensuite full bathroom. The living space is open and airy, with ample natural light, vaulted ceilings, hardwood floors and a gas fireplace. The large loft could be an office, den, or creative studio space. The walk-in attic provides additional storage. An ideal investment in historic Chestertown.

327 Cannon St, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

3 Beds ⋅ 4 Baths

Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic District The Bedingfield Hands House, circa 1750, is more than a home—it's a living piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make historic homes so special. History is woven into every corner of the property—from the prominence of past owners down to the foundation, which contains the mast of a ship. The only home downtown with such a generous private front courtyard framed by mature landscaping, vibrant seasonal gardens, brick herringbone paths, and mature trees that create a peaceful retreat just steps from town. Whether enjoying a quiet morning coffee, entertaining guests, or simply admiring the blooms, the outdoor spaces are truly a stand-out feature. Approaching the home, guests are welcomed by a wide red front door, a traditional symbol of hospitality in early America, inviting visitors inside just as it has for centuries. Inside, approximately 2,472 square feet of thoughtfully preserved living space blends historic character with modern comfort. Original wide-plank hardwood floors, period moldings and built-in cabinetry, reflect the home's 18th-century origins, while updated kitchens, baths, and central air/heat provide the conveniences expected today. To the right of the grand foyer, a cozy study lined with built-in bookshelves provides the perfect home office or library and could easily be converted into a first-floor bedroom for those seeking single-level living flexibility. A first floor full bathroom with walk in shower is located conveniently around the corner straight through the foyer. To the left of the foyer and at the forefront of the home, the stunningly preserved parlor, featuring 12x12 wavy glass windows, original panel walls and stunning gas fireplace with pine panel surround, offers an elegant setting for entertaining guests or enjoying quiet evenings at home. Just beyond, the large dining room serves as a memorable gathering space, complete with another fireplace, built-in cabinetry, and a charming pop-out window seat overlooking the side gardens. Just beyond that is a chef's kitchen featuring updated appliances, abundant storage cabinetry, generous island workspace, and a soaring tapered tray ceiling that creates an airy and inviting atmosphere. The kitchen breakfast nook is highlighted by panoramic bay window wall. Off the breakfast nook is a convenient half bath and steps to the side courtyard with pergola and a screened porch. The garage—another rarity in the Historic District—provides valuable storage and convenience. Upstairs, the spacious primary suite blends historic character with thoughtful updates, featuring a practical double closet and an en-suite bath highlighted by distinctive MacKenzie-Childs tile floors and decorative vanity hardware. Two additional generously sized bedrooms and a full bathroom provide comfortable accommodations for guests. Beyond its appeal as a private residence, it has proven itself as one of Chestertown's most successful Airbnb properties, generating approximately $32,000 in bookings last year. Whether you're seeking a full-time residence, weekend retreat, or income-producing investment, this property offers exceptional flexibility. Furniture is negotiable for a truly turnkey opportunity. Step outside and enjoy everything that makes Chestertown so beloved. Stroll to art galleries, locally owned shops, restaurants, the farmers market, and waterfront parks along the Chester River. Enjoy annual traditions such as the Tea Party Festival, Downrigging Weekend, and Dickens of a Christmas, all just moments from your front door. Become the steward of a treasured landmark while enjoying the comfort, beauty, and lifestyle that have made it one of Chestertown's most admired homes for generations.

106 Queen St S, Chestertown

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

3 Beds ⋅ 4 Baths

**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

104 Landing Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. 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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