Nestled among beautifully landscaped gardens and mature fruit trees, this exceptional 5-bedroom, 2-bath residence offers timeless New England charm in the heart of Littleton, one of New Hampshire's most sought-after communities. Just moments from the award-winning Main Street, this home blends gracious living with the warmth and character that make Littleton such a treasured destination. A welcoming foyer introduces spacious living and dining rooms designed for both everyday comfort and memorable gatherings. The thoughtfully designed main level also features a generous kitchen, two bedrooms, a full bath, and a convenient mudroom with direct access to the paved circular driveway. Two staircases, including one equipped with a chair lift, provide easy access to the second floor. The private upper level offers a peaceful retreat featuring a spacious primary bedroom with its own deck overlooking the gardens, a home office or study, two additional bedrooms, a playroom, laundry room, and a second full bath. Step outside and enjoy the best of Littleton's vibrant lifestyle. Stroll to locally owned boutiques, cafés, breweries, acclaimed restaurants, and the scenic Riverwalk with its iconic covered pedestrian bridge spanning the River. Outdoor enthusiasts will appreciate immediate access to the Ammonoosuc Recreational Rail Trail and the endless four-season recreation of the White Mountains, including hiking, skiing, mountain biking, golf, kayaking, fishing, and snowmobiling. Served by the highly regarded Littleton School District, this exceptional property is equally suited as a distinguished year-round residence, a refined vacation retreat, or a valuable investment. Offering an enviable combination of location, character, accessibility, and lifestyle, 109 South Street presents a rare opportunity to experience the very best of Northern New Hampshire living.