Rare opportunity to own nearly 2 acres in historic Anchorage, offering privacy and character in the state-leading Anchorage Independent K-8 School District. Priced below appraised value, this five-bedroom home blends timeless charm with thoughtful modern updates. The first floor features three bedrooms including the primary suite with soaring ceilings, soaking tub, and walk-in shower. You will also find hardwood floors, a sunken living room with original brick accents, and a gourmet kitchen with birds-eye maple cabinetry, granite counters, large island, and JennAir appliances. Upstairs includes two additional bedrooms and a versatile bonus space ideal for an office, playroom, or media room. The home provides plenty of storage throughout, supporting both everyday living and long-term organization. Outdoors, enjoy a serene park-like setting with two decks, a patio, new privacy fencing, and a custom-built playhouse crafted from wood reclaimed from the original barn once located on the property. Additional highlights include an extra-deep two car garage, separate converted gym space, circular driveway, and an updated high-efficiency HVAC system and tankless water heater. This home offers the charm and small town feel of Anchorage with no HOA while being moments from Shelbyville Road and the shopping and dining of Middletown, creating a perfect blend of privacy and convenience.