Orchard Hill Homes with Poolside Lot description

Welcome to Orchard Hill, a picturesque subdivision nestled in the heart of Chestertown, Maryland, within the charming Kent County. This serene community is a hidden gem, offering a perfect blend of tranquility and modern living. With its lush landscapes and friendly atmosphere, Orchard Hill is an ideal place for families, retirees, and anyone looking to embrace a peaceful lifestyle.

One of the standout features of Orchard Hill is its stunning homes, many of which boast poolside lots that invite you to bask in the sun and enjoy leisurely afternoons by the water. Imagine stepping out of your back door to a private oasis where you can unwind, entertain, or simply soak up the beauty of nature. These homes are designed with elegance and comfort in mind, providing ample space for relaxation and gatherings with loved ones.

The community itself is enriched by its proximity to Chestertown’s vibrant downtown area, where you can explore quaint shops, delightful eateries, and cultural attractions. Outdoor enthusiasts will appreciate the nearby parks and waterfront access, perfect for kayaking, fishing, or enjoying a scenic stroll along the Chester River.

In Orchard Hill, you’ll find not just a home, but a lifestyle. The combination of beautiful residences with poolside lots, a welcoming community, and easy access to the best of Chestertown makes this subdivision a truly special place to call home. Come discover Orchard Hill, where your dream home awaits amidst the beauty of Maryland’s Eastern Shore!

Newest Orchard Hill Homes with Poolside Lot description

$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 inground pool serves as the crown jewel of the outdoor space, newly upgraded with all-new mechanicals including a dedicated heater. 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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