Oak Hollow Homes with Traditional Style

Welcome to Oak Hollow, a picturesque subdivision nestled in the heart of Chestertown, Maryland, within the charming Kent County. This delightful community combines the allure of traditional architecture with the serene beauty of nature, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle.

Oak Hollow is characterized by its stunning homes that embody the timeless charm of traditional style. With their classic brick facades, gabled roofs, and inviting front porches, these residences exude warmth and character. Inside, you’ll find spacious layouts, elegant finishes, and modern amenities that cater to today’s discerning homeowner while maintaining a nod to the past.

The subdivision is surrounded by lush greenery, offering residents a tranquil escape from the hustle and bustle of city life. Enjoy leisurely strolls along tree-lined streets, where friendly neighbors greet you with a smile. Oak Hollow is not just a place to live; it's a community where memories are made, and friendships flourish.

Families will appreciate the proximity to excellent schools, parks, and recreational facilities, ensuring that there’s always something to do. The vibrant Chestertown downtown area, with its unique shops, restaurants, and cultural events, is just a short drive away, providing the perfect blend of small-town charm and modern conveniences.

Discover the enchanting lifestyle that awaits you in Oak Hollow, where traditional elegance meets the beauty of nature. Your dream home is waiting for you in this idyllic community!

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

Start Your Search