Timeless charm meets thoughtful updates in this classic 2-story home built in 1890, ideally located on historic Court Ave just one block from the town square. Offering 2,396 square feet, 3 bedrooms, and 2.5 baths, this beautifully maintained home blends original character with modern functionality in all the right ways. The showstopping custom-designed kitchen is truly the heart of the home, featuring a 10' breakfast bar, appliance garage, abundant cabinetry, pantry cabinets with pull out drawers, and an incredible amount of storage that is rarely found in homes of this era. Original hardwood floors, beautiful original staircase, oversized windows, and generous natural light create a warm and inviting atmosphere throughout. Enjoy hosting gatherings in the formal dining room or relaxing in the family room while taking in views of the courthouse right from your windows. Additional highlights include a new roof, maintenance-free deck, oversized 3.5 car garage, and convenient outside access to the basement. The 3.5 car garage is also unexpected with homes of this era. There is extra shop space for the serious woodworker. Don't miss the original doorbell on the door near the staircase. Full of charm, space, and timeless appeal, this exceptional property offers the perfect blend of historic beauty and everyday comfort in one of Winterset's most desirable locations. 4th bedroom option on the 1st floor with a 3/4 bath. Updates include: new siding, windows and insulation.