Chestertown Homes with Driveway (Gravel) Parking features

Chestertown Homes with Driveway (Gravel) Parking features

Welcome to Chestertown, Maryland—a charming town steeped in history and bursting with character. Nestled along the banks of the Chester River in Kent County, Chestertown is known for its picturesque streets, vibrant arts scene, and a strong sense of community. With its rich colonial heritage, visitors and residents alike are drawn to its quaint shops, delightful eateries, and historic landmarks, making it a perfect place to call home.

One of the standout features of homes in this lovely town is the availability of properties with gravel driveway parking. These homes not only offer a rustic charm but also provide practical benefits. A gravel driveway enhances the aesthetic appeal of your property while offering ample space for parking. It’s a perfect solution for those who appreciate a more natural, laid-back vibe, allowing for easy access to your home while blending seamlessly with Chestertown's scenic surroundings.

Imagine coming home to a cozy house with a gravel driveway, where you can unwind after a day of exploring local boutiques or enjoying a leisurely stroll along the riverfront. The convenience of having your own parking space means you can invite friends and family over without worrying about parking constraints, making gatherings even more enjoyable.

Chestertown is not just a place to live; it’s a lifestyle. Embrace the charm of this historic town while enjoying the practical benefits of homes with gravel driveway parking. Whether you’re looking to settle down or invest in a vacation property, Chestertown is waiting to welcome you home.

Newest Chestertown Homes with Driveway (Gravel) Parking features

2 Beds ⋅ 2 Baths

Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farmhouse charm. Inside, you’ll find an open floor plan with luxury vinyl plank flooring throughout the main living areas. The living room offers a cozy space to relax and unwind. The updated kitchen is the heart of the home and features beautiful finishes and newer appliances, making it a great space for cooking and gathering. The home features two bedrooms, including a spacious primary bedroom, and two full bathrooms that have both been nicely updated. The spacious laundry room/mudroom provides plenty of room and adds everyday convenience. Enjoy your morning coffee or unwind at the end of the day on the inviting front porch, a great spot to sit back and enjoy the peaceful surroundings. Outside, you’ll find a large half-acre lot that backs to farmland, offering a beautiful setting. There’s plenty of room to enjoy the outdoors, garden, or let the kids and pets play. The gravel driveway provides parking for up to four vehicles. If you’re looking for a home that has been beautifully updated while still keeping that cozy farmhouse feel, this one is worth a look. Come see everything this Fairlee home has to offer!

22974 Bay Shore Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

3 Beds ⋅ 1 Baths

This adorable rancher combines a fresh, updated interior with plenty of outdoor space to enjoy. Come step inside to a bright and welcoming home filled with natural light, LVP flooring and a modern, neutral color palette that flows throughout. The crisp white kitchen keeps things light and timeless, while the spacious living room offers plenty of room to relax, gather and make the space your own. Three comfortably sized bedrooms provide flexibility for sleeping, working from home or creating a dedicated hobby space. The updated full bathroom continues the fresh aesthetic with tile flooring and a coordinating white vanity. Even the everyday necessities have been thoughtfully considered with a dedicated laundry closet featuring a full-size washer and dryer plus shelving for additional storage. Outside, the large corner lot gives you room to spread out without sacrificing that familiar neighborhood feel. Step through the rear entry onto the newer paver patio, perfect for grilling, outdoor dining or relaxing while overlooking the playset and backyard. Vinyl privacy fencing, a storage shed, long driveway and plenty of usable outdoor space round out the property. With main level living, thoughtful updates and neighborhood vibes without the community HOA, this home offers an easy, comfortable lifestyle with plenty of opportunity to make it your own.

104 Lincoln Dr, Chestertown

Listing courtesy of RE/MAX Executive. Contact:

4 Beds ⋅ 2 Baths

A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and the quiet character that comes from decades of careful ownership. Step inside and the home tells its story with original trim, classic proportions and timeless architectural touches. The two-story split-level floor plan offers a thoughtful separation of living and sleeping spaces, with a sun-filled sunroom that works beautifully as a screened porch when the doors are all open or as extra living space during the shoulder seasons. Two of the bedrooms sit on the upper level, while two large bedrooms flow comfortably below. Out back, the large, gently sloped corner lot offers privacy, mature trees, and room to garden, entertain, or simply enjoy a quiet afternoon. The setting feels tucked away, while the rest of Chestertown is just a short jaunt from the front door. The two-bay carport keeps your vehicles safe from the elements in the wide stone driveway. What truly sets this home apart is its condition. It has been maintained impeccably — spotlessly clean, carefully tended, and gently lived in. The HVAC system is new, and the kitchen and laundry appliances are all young as well, giving the next owner the best of both worlds: classic character on the outside, modern mechanicals where it counts. The remaining finishes offer a thoughtful canvas for the next owner to put their own stamp on it, with the confidence that the bones and the care have already been handled. Classic character, pristine condition, and convenience to it all.

200 Manor Ave, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

4 Beds ⋅ 5 Baths

Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away. The home features 4 bedrooms and 5 full bathrooms, plus a large loft that could be used as an additional bedroom. The large eat-in kitchen has expansive windows that perfectly frame the water view. A great spot for entertaining! Doors in the kitchen lead to the waterfront deck, spanning the front of the home. A new roof was installed in June, 2026. In both sitting rooms, you’ll find fireplaces that have been conveniently updated to propane. The first-floor primary bedroom opens up to the waterfront deck and offers a fantastic water view, as well as a large bathroom that was recently updated. Upstairs you’ll find two waterfront bedrooms, one with an updated attached bath. There's a second full bathroom and ample closet space in the hallway. Downstairs, there are two additional full bathrooms and a large bedroom. Above the kitchen sits the light-filled loft, a great office, studio, or extra bedroom. The exterior has a generous front porch, outdoor shower, circular drive, 2-car garage, fenced dog run, and additional garage space connected to the basement. This light-filled waterfront property is located 15 minutes away from the waterfront community of Rock Hall and historic Chestertown.

22470 Fairgale Farm Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

3 Beds ⋅ 2 Baths

* SELLER IS OFFERING A 1 YEAR HOME WARRANTY WITH ACCEPTABLE OFFER * Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walking distance to Tolchester Marina and Shanty Beach Bar, offering outdoor entertainment throughout the summer months. Approximately 10 minutes to Rock Hall and 20 minutes to Chestertown, this home offers the perfect blend of comfort and rural living. Enjoy all that Tolchester has to offer at 8706 Elm.

8706 Elm Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

5 Beds ⋅ 3 Baths

6746 Quaker Neck Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

4 Beds ⋅ 3 Baths

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.

23043 Bay Shore Spur, Chestertown

Listing courtesy of Rock Hall Properties 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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