Oak Hollow Homes with Traditional Style

Welcome to Oak Hollow, a charming subdivision nestled in the picturesque town of Chestertown, Maryland. This serene community, located in Kent County, offers a harmonious blend of natural beauty and traditional elegance, making it one of the most sought-after neighborhoods in the area.

Oak Hollow is characterized by its stunning homes that showcase traditional architectural styles, exuding warmth and timeless appeal. Each residence is thoughtfully designed, featuring classic elements such as gabled roofs, inviting front porches, and beautifully landscaped yards. These homes are not just structures; they are havens of comfort and style, perfect for families and individuals alike.

Living in Oak Hollow means immersing yourself in a community that values tranquility and connection. The tree-lined streets are perfect for leisurely strolls or evening bike rides, and the close-knit atmosphere fosters friendships among neighbors. With ample green spaces and parks nearby, residents can enjoy outdoor activities, picnics, or simply bask in the beauty of nature.

Moreover, Oak Hollow's prime location in Chestertown provides easy access to local amenities, including quaint shops, delightful eateries, and cultural attractions that celebrate the town’s rich history. Whether you are exploring the charming downtown area or enjoying a day by the Chester River, there’s always something to do.

Discover your dream home in Oak Hollow, where traditional style meets modern living in a community that feels like family. Embrace the lifestyle you’ve always wanted in this enchanting enclave of Chestertown!

Newest Oak Hollow Homes with Traditional Style

$275,000

3 Beds ⋅ 3 Baths

Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly positioned just minutes from historic downtown Chestertown, local schools, and the YMCA—blending everyday convenience with a welcoming community atmosphere. Enter through the ground floor, where a flexible bonus room and one-car garage offer endless possibilities for a home office, gym, or recreation space. The heart of the home sits on the main level, featuring a generous living room and an eat-in kitchen that opens to a private rear deck—the perfect spot to unwind and look out at the wooded backdrop. Upstairs, you will find three comfortable bedrooms, including a primary suite with a private bath, alongside a dedicated laundry area. Turn-key and low-maintenance, this property is a fantastic opportunity for first-time buyers, downsizers, and investors alike.

104 Acorn Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

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