Step into the timeless charm of this character-filled home, originally built in the 1920s and offering a unique multi-level layout with inviting living spaces throughout. Upon entering, you'll find the kitchen conveniently located on the lower level, featuring a new butcher block countertop and newer appliances. Just beyond the kitchen is a versatile finished bonus room—perfect as a dining room, home office, reading nook, or sitting area—with French doors leading to the patio and charming herb garden, creating a wonderful space to enjoy the outdoors. The main level offers a warm, welcoming living room with the primary bedroom, providing a comfortable setting for everyday living and entertaining. The updated full bathroom features stylish shiplap accents and durable luxury vinyl flooring, blending modern touches with the home's classic character. The upper level is dedicated to two additional bedrooms, offering privacy and a functional separation of living and sleeping spaces. With its distinctive floor plan, original charm, and thoughtful updates—including a newer roof, siding, windows, and boiler and hot-water heater, completed within the last five years—this home offers a solid foundation for its next owner. Whether you're looking to move right in and update over time or add your own personal style from the start, this property presents an excellent opportunity to build equity while enjoying everything it has to offer. Outside, the property offers approximately 2 acres of open space, with room for gardening, entertaining, recreation, or simply enjoying the quiet surroundings. The detached garage, mature landscape, and spacious yard create the ideal setting for those looking for a little extra room to spread out. Conveniently located just minutes from shopping, restaurants, schools, and major commuter routes, you'll enjoy easy access to Middletown, Goshen, Warwick, and the surrounding Hudson Valley. Outdoor enthusiasts will appreciate nearby Highland Lakes State Park, the Heritage Trail, local wineries, breweries, golf courses, and farmers' markets. Popular destinations such as LEGOLAND New York Resort, Resorts World Catskills, and The Kartrite Resort & Indoor Waterpark are all within easy driving distance, making this location ideal for both everyday living and weekend adventures. If you've been searching for a property with solid structural updates, acreage, and the opportunity to add value through cosmetic improvements, 122 Castle High Road is a fantastic opportunity to create a space that reflects your own style while enjoying everything Orange County has to offer. Minisink School District