Step into your own private world, just 2.75 miles from Historic Downtown Chestertown. Tucked away at the rear of a mostly wooded 19+/- acre parcel, this exceptionally well-maintained property offers a rare combination of privacy, space, versatility, and convenience. At the heart of the property is a beautifully maintained brick residence overlooking a picturesque private pond, creating a peaceful setting that feels worlds away while remaining just minutes from town. The thoughtfully designed home is move-in ready and offers a comfortable, functional layout with quality finishes and inviting living spaces throughout. The first floor features a welcoming entry, upgraded gourmet kitchen with adjoining dining area, a spacious primary suite, and comfortable living areas that open to an expansive deck overlooking the pond. Whether enjoying a quiet morning or entertaining family and friends, the views and setting provide a stunning backdrop. Upstairs, you'll find three additional generously sized bedrooms and two full baths, providing plenty of room for family and guests. The finished walkout lower level adds another dimension to the home and offers tremendous flexibility as a game room, recreation space, home theater, gym, or private retreat, with direct access to the grounds and pond beyond. Adding even more value are two substantial, well-constructed outbuildings, each offering an incredible range of possibilities. Whether envisioned as a home office, woodworking or mechanical shop, hobby space, equipment storage, studio, or a combination of uses, these buildings make the property especially well-suited for someone seeking room to live, work, create, and store, all in one location. Surrounded by mature woods, expansive lawn, and the tranquil pond, the property offers a wonderful sense of seclusion without sacrificing proximity to the shops, restaurants, waterfront, and charm of Historic Chestertown. Properties offering this combination of acreage, privacy, substantial improvements, and proximity to town rarely become available. This is truly a one-of-a-kind Eastern Shore property that must be experienced in person to fully appreciate all it has to offer.