Oak Hollow Townhomes for Sale

Welcome to Oak Hollow, a charming subdivision nestled in the heart of Chestertown, Maryland. This picturesque community offers a unique blend of small-town charm and modern convenience, making it an ideal place for families, young professionals, and retirees alike. With its tree-lined streets and beautifully landscaped parks, Oak Hollow is a haven for those who appreciate nature and a tight-knit community atmosphere.

The townhomes for sale in Oak Hollow are designed with comfort and style in mind. Each residence features spacious floor plans, contemporary finishes, and ample natural light, creating inviting spaces for family gatherings and entertaining friends. Many homes come equipped with modern amenities, including gourmet kitchens, cozy living areas, and private outdoor spaces, perfect for enjoying the serene surroundings.

Oak Hollow is conveniently located near the vibrant downtown Chestertown, where residents can explore a variety of shops, restaurants, and cultural attractions. The town is known for its rich history and waterfront charm, offering plenty of opportunities for outdoor activities such as boating, fishing, and hiking along the scenic Chester River.

Families will appreciate the proximity to highly-rated schools and community resources, ensuring that every resident feels at home. With a strong sense of community and a commitment to preserving the natural beauty of the area, Oak Hollow is not just a place to live; it’s a lifestyle.

If you’re looking for a welcoming community with beautiful townhomes for sale, Oak Hollow in Chestertown, MD, is the perfect destination for your next chapter. Come and discover the charm of Oak Hollow today!

Newest Oak Hollow Townhomes for Sale

$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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