Orchard Hill Homes with Craftsman Style

Welcome to Orchard Hill, a picturesque subdivision nestled in the charming town of Chestertown, Maryland. This hidden gem in Kent County offers a delightful blend of natural beauty and modern living, making it the perfect place to call home. Surrounded by lush orchards and serene landscapes, Orchard Hill embodies the tranquil lifestyle many seek while still being conveniently located near local amenities and attractions.

The homes in Orchard Hill are a stunning representation of Craftsman-style architecture, characterized by their warm, inviting aesthetics and meticulous craftsmanship. These residences often feature wide porches, exposed wooden beams, and unique stonework, all designed to create a harmonious blend with the surrounding environment. Inside, you'll find open floor plans that maximize space and light, with cozy nooks perfect for family gatherings or quiet evenings by the fireplace.

Living in Orchard Hill means embracing a community that values quality of life. Residents enjoy access to nearby parks, walking trails, and the beautiful Chester River, perfect for outdoor enthusiasts and nature lovers alike. The historic charm of Chestertown, with its quaint shops, delightful dining options, and vibrant arts scene, is just a stone's throw away.

Whether you’re a first-time homebuyer or looking to settle down in a peaceful retreat, Orchard Hill offers a unique opportunity to experience the best of Maryland living. Come and explore this enchanting community where Craftsman-style homes meet the beauty of nature, and where every day feels like a getaway. Welcome home!

Newest Orchard Hill Homes with Craftsman Style

$824,900

5 Beds ⋅ 4 Baths ⋅ MDKE2006786 MLS ⋅ ACTIVE Status

Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort. Upon arrival, the welcoming foyer makes a memorable first impression, framed by detailed custom millwork and flanked by a private executive office and a sophisticated study or formal dining space. Moving inward, the magnificent two-story great room commands attention with its soaring ceilings and a cozy gas fireplace crowned by a classic raised brick hearth. At the heart of the main level lies a gourmet kitchen designed for grand gatherings, showcasing fresh luxury vinyl flooring, select new appliances, and a stunning quartz-topped center island with a prep sink that easily reconfigures for multi-purpose hosting. Sunbeams flood the adjoining sunroom, creating a seamless transition to the outdoors while mirroring the warmth of the home’s main-floor primary suite. This private retreat features a spacious walk-in closet and a newly remodeled, spa-inspired bath complete with new quartz double vanities, sleek updated fixtures, a large walk-in shower, and an exquisite standalone soaking tub. Offering unmatched independence and comfort, a fully self-contained ground-level suite on the lowest level serves as the ultimate in-law or guest quarters. Complete with its own private ground-level entrance, open-concept kitchen and living area, dedicated laundry, and an accessible bath with a walk-in shower, this wing ensures total convenience without sacrificing style. A new addition to the lower level unlocks movie-theater magic with a fully furnished screening room ready for immediate enjoyment. Upstairs, four generously proportioned bedrooms accompany a beautifully refreshed hall bath. The exterior grounds are nothing short of a resort-style paradise. Step out onto the back porch to take in sweeping views of the lush landscape and expansive partially fenced yard. The sparkling in-ground pool serves as the crown jewel of the outdoor space, newly upgraded with all-new mechanicals including a dedicated heater. The owners have ordered a new, heavy duty liner, perfect for pets and kids, to be installed with the closing of the pool around the end of September. Surrounding the water, extensive custom hardscaping leads to a fireside gathering area, while an oversized gazebo with an outdoor fan offers a shady retreat on warm afternoons. With a brand-new roof installed in 2026, a newly resurfaced driveway, and space remaining for future additions, this estate represents a rare opportunity to experience sophisticated countryside living at its finest and, less than 5 minutes from Chestertown's restaurants, shopping, and Farmer's Market. Updates to the home are available in Documents

8999 Orchard Dr, Chestertown

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