Set on nearly two private acres in historic Anchorage, this five-bedroom home offers a rare combination of privacy, character, and thoughtful updates within the Anchorage Independent School District. The main level features three bedrooms, including a primary suite with soaring ceilings, a soaking tub, and walk-in shower, along with hardwood floors, a sunken living room with original brick accents, and a well-appointed kitchen with birds-eye maple cabinetry, granite counters, large island, and JennAir appliances. Upstairs, two additional bedrooms and a flexible bonus space provide room for a home office, media area, or playroom. Outdoors, the park-like setting includes two decks, a patio, new privacy fencing, and a custom playhouse crafted from reclaimed barn wood from the original barn on the property. Additional highlights include an extra-deep two-car garage, separate finished space, circular driveway, and updated high-efficiency HVAC with a tankless water heater. A rare offering with convenient access to Shelbyville Road and Middletown amenities.