Chestertown Historic District Homes with Paved Parking Parking desc

Welcome to the Chestertown Historic District, a captivating slice of Maryland's rich heritage nestled in the charming town of Chestertown. This vibrant community is a treasure trove of history, where colonial architecture meets modern living, creating a unique blend that appeals to both history enthusiasts and contemporary homeowners alike.

As you stroll through the tree-lined streets, you'll be enchanted by the beautifully preserved 18th and 19th-century homes, each telling its own story. The Chestertown Historic District is not just a place to live; it’s a lifestyle steeped in tradition, with local shops, art galleries, and delightful eateries just a stone's throw away. You can enjoy leisurely walks along the Chester River, partake in local festivals, or simply soak in the serene ambiance that this historic district offers.

For those seeking the perfect home in this picturesque area, many properties come with the added convenience of paved parking, ensuring that your daily comings and goings are as effortless as possible. Imagine returning to your charming abode after a day of exploring, with a dedicated space waiting just for you.

Whether you’re drawn to the allure of historic architecture or the vibrant community spirit, the Chestertown Historic District offers an exceptional living experience. Embrace the charm of this unique neighborhood, where every corner has a story, and every home is a gateway to a rich past. Discover your dream home in Chestertown today and become a part of this enchanting community!

Newest Chestertown Historic District Homes with Paved Parking Parking desc

$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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