Chestertown Historic District Homes with Garden/Lawn View

Welcome to the enchanting Chestertown Historic District, a hidden gem nestled in the heart of Maryland's picturesque Kent County. This charming area, steeped in rich history and vibrant culture, offers an idyllic setting for those seeking a unique blend of modern comfort and timeless elegance.

The Chestertown Historic District is characterized by its beautifully preserved 18th and 19th-century architecture, showcasing a delightful array of Federal and Victorian-style homes. As you stroll through the tree-lined streets, you'll be captivated by the allure of historic charm combined with the warmth of a close-knit community. Each home tells a story, and many boast stunning gardens and lush lawns that create a serene backdrop for outdoor living.

For those who cherish the beauty of nature, the homes in this district offer breathtaking garden and lawn views that invite tranquility and relaxation. Imagine sipping your morning coffee on a sun-drenched porch, surrounded by vibrant blooms and the gentle rustle of leaves. The meticulously maintained gardens not only enhance the aesthetic appeal of each property but also provide a sense of privacy and peace, perfect for unwinding after a busy day.

Living in the Chestertown Historic District means embracing a lifestyle where history meets modern convenience. With quaint shops, delightful eateries, and cultural attractions just a stone's throw away, residents enjoy the best of both worlds. Whether you're exploring the waterfront or attending a local festival, the charm of this community is undeniable.

Discover your dream home in the Chestertown Historic District, where history, beauty, and community come together to create an extraordinary living experience.

Newest Chestertown Historic District Homes with Garden/Lawn View

$898,000

3 Beds ⋅ 4 Baths

Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. You'll love the warm hardwood floors throughout the home. On the second level you'll find two bedrooms and two bathrooms. The third bedroom encompasses the entire third floor and has a great view of the Chester River. You'll enjoy the large back balcony with views of historic Chestertown. The third level could be used as the primary bedroom; there is a large full bathroom and closet. The townhomes have a private driveway, so you'll never worry about finding a parking space. Take advantage of the easy access to Wilmer Park and Chestertown Marina, located just across the street. This townhouse is located in the heart of all Chestertown has to offer! Just a short distance to shops, restaurants, renowned bakeries, and the year-round farmers market by Fountain Park. You will have a front-row seat to the Downrigging Festival! Not to mention the many festivals held in downtown Chestertown throughout the year.

226 S Water St, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$419,999

4 Beds ⋅ 2 Baths

ALSO AVAILABLE FOR LEASE: Please reach out to agent for details. This charming 1916 home in Chestertown's historic district is in a quiet neighborhood next to Washington College, just a short walk from downtown and the waterfront. Three finished levels and high ceilings plus bright, natural light make the home feel airy and spacious. Historic features include original heart-pine hardwood floors and beautiful molding throughout. The first floor includes an adorable kitchen with butcher block countertops, as well as a living room, dining room, and 3/4 bathroom. Upstairs, you’ll find three bedrooms, a full bath, and a walk-in closet. The third floor offers a lofted bedroom and bonus room - perfect for a playroom, office, or workout room. The mahogany-floored porch has interchangeable screens and windows, converting easily from a screen porch into a sunroom. Outside, a new six-foot pressure-treated pine fence provides privacy for the backyard, with an extra fenced garden area. The driveway has off-street parking for two vehicles. Additional home updates include a tankless hot water heater, high-efficiency 3-zone boiler, whole-house surge protector, upgraded panel, and Kenmore gas range. In summer 2025, the current owners invested in over $60,000 in major renovations hoping to stay for many years. They replaced the roof, updated the electrical wiring, and painted the interior. All upgrades were intended to be enjoyed by current homeowners. Unfortunately, they found that they had to move out of state to be closer to a new job.

222 Mount Vernon Ave, Chestertown

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

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