Some homes are simply different, and this one is truly special! Set on approximately 3 acres, this remarkable circa-1800 Colonial has the kind of charm and presence you simply don't find in newer homes. From the moment you arrive, there is a feeling that this is a home with a story, cared for and enjoyed through generations. Inside, original character is everywhere you look. Beautiful wide-plank pine floors, hardwood floors with intricate inlay, crown molding, original fireplaces, a charming tin ceiling and built-in cabinetry are just some of the details that make this home so unique. With approximately 3,960 square feet of living space, generously sized rooms and multiple staircases, there is plenty of flexibility for everyday living, entertaining, working from home or simply enjoying the character of an older home. The kitchen is full of personality, featuring an original brick fireplace, a commercial-grade stove and a new Bosch dishwasher and eat-in kitchen for everyday meals. The formal dining room and living room with fireplace are complemented by a spacious great room with its own entrance, a first-floor bedroom and full bathroom. An oversized sliding glass door opens to the gorgeous patio, creating a natural connection between the home and its beautiful setting. While its historic character remains at the heart of the home, numerous updates add modern convenience, including a newer roof on the main house, geothermal heating, a whole-house generator, new Andersen windows, a new sliding glass door, spray foam insulation, an updated electrical panel and a whole-house water filtration system. A newer washer and dryer, a charming Dutch door at the side entrance and two upstairs rooms offering additional flexibility add to the home's appeal. Outside, a U-shaped driveway provides ample parking, while a charming chicken house, garden shed and fenced-in garden add to the property's country character. Mature trees, including towering white pines, horse chestnut, walnut, maple and oak, create a beautiful and peaceful setting. Enjoy the space, privacy, and tranquility of the property while still being conveniently located near major highways, shopping, restaurants and entertainment, making it easy to enjoy everything the Middletown area has to offer. This is not a cookie-cutter home, and that is exactly what makes it so special. For someone who appreciates architecture, history and craftsmanship, 59 Webb Road offers a rare opportunity to own a piece of Middletown history, ready for its next chapter!