Chestertown Historic District Homes with Level Lot features

Welcome to the Chestertown Historic District, where timeless charm meets modern convenience! Nestled in the heart of Kent County, Maryland, this enchanting neighborhood is a treasure trove of history and architectural beauty. With its cobblestone streets, quaint boutiques, and vibrant waterfront, Chestertown invites residents to embrace a lifestyle steeped in rich heritage and community spirit.

The Chestertown Historic District boasts an array of homes that perfectly blend historic character with contemporary comforts. Each residence tells a story, showcasing an impressive variety of architectural styles, from Federal to Victorian. One of the standout features of many homes in this district is the level lot, offering a spacious and inviting outdoor area that’s perfect for entertaining, gardening, or simply enjoying the serene surroundings.

Imagine stepping out onto your beautifully landscaped yard, where the gentle rustle of leaves and the sweet scent of blooming flowers create a peaceful oasis right in your backyard. The level lots provide ample space for outdoor activities, whether it’s a summer barbecue with friends or a quiet evening under the stars.

Living in the Chestertown Historic District means you’re just a stone’s throw away from local shops, art galleries, and delightful eateries, all while being surrounded by the stunning natural beauty that Maryland has to offer. With a warm sense of community and a rich cultural tapestry, this district is more than just a place to live; it’s a lifestyle. Discover your dream home in Chestertown today and become a part of this captivating historic enclave!

Newest Chestertown Historic District Homes with Level Lot features

$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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