Step back into American history at Hillcroft, a distinguished county estate with roots tracing back to the 1700s. Built in five stages, this Colonial-style home stands along the historic Great Wagon Trail and spans 21 picturesque acres. Featuring 4 bedrooms, each with en-suite bath, with potential for an additional bedroom, and a total of 5.5 bathrooms, Hillcroft blends historic charm with modern comforts. Notable features include 9 fireplaces, 5 staircases, wide heart pine floors, reclaimed paneling from a salt house and tobacco barn, hand-hewn beams, and doors from Patrick Henry's law office. Modern updates include an enlarged, renovated kitchen, 3 full baths have been renovated, central heating & cooling, and a lower-level efficiency apartment with private entrance and accessibility. A cozy 2-bedroom log guest house offers excellent potential for rental or Airbnb income or perfect for a mother-in-law. Additional improvements include a detached 2-car garage with extra storage, brick workshop, and open garage for RV or boat storage. Outdoor spaces feature a formal boxwood garden leading to a romantic gazebo, a fully functional pool with new pump, and garden house which once served as a doctor's office. Conveniently located near the bypass, Hillcroft is a rare, once-in-a-generation offering - steeped in history yet thoughtfully updated for today's living. Come experience the legacy for yourself.