One-of-a-kind country estate on 33.7 acres of wooded, rolling hills in Hagerstown! This exceptional property offers a rare multi-home setup ideal for extended family living, guest accommodations, or income potential. The main residence at 7840 N Jacksonburg Rd features approximately 4,600 sq ft of living space, a 3-car garage, and two spacious primary suites, providing comfort, flexibility, and thoughtful design throughout. Quality craftsmanship is evident with 36-inch solid 6-panel wood doors throughout, wide hallways designed to accommodate wheelchairs if needed, and soaring cathedral ceilings that create an open, airy feel. A shared common kitchen connects the living spaces, making this property ideal for multi-generational living or hosting guests with ease. The home offers exceptional functionality with a full unfinished basement featuring a second laundry area, workshop, safe room, and ample storage space. There are two staircases leading into the home, one equipped with a chair lift, plus an additional two staircases within the main house, providing convenient access throughout. Comfort is ensured year-round with two heating and A/C systems, complemented by the warmth and charm of two wood-burning stoves. Outdoors, the land truly shines—33.7 acres of wooded, rolling hills offering privacy, scenic views, and endless possibilities. A turn-of-the-century barn with newer metal roof and siding adds both character and utility, while the spring house highlights the property’s rich rural heritage. The secondary home at 7896 N Jacksonburg Rd is a charming 2,000 sq ft guest house, built in 1903, featuring 2 bedrooms and 1 bathroom—perfect for guests, extended family, caretakers, or rental income. This property is ideal for a private retreat, hobby farm, multi-generational living, or investment opportunity. Be sure to review all the amazing photos to fully appreciate everything this unique estate has to offer. Schedule your private showing today with the Duning Team.