Experience timeless charm in this beautifully updated antebellum home, ‘Greenwood’, located in historic Holly Springs. Featuring elegant Federal-style architecture with Greek Revival elements, the property offers exceptional comfort for everyday living.Step through the double-leaf front entrance into a foyer with a crystal chandelier. To the right, find the formal parlor with a gas fireplace and access to a covered porch. On the other side, a spacious formal dining room awaits.Through the foyer, ‘The Hub’ serves as a central connecting point to various downstairs rooms, including the kitchen, den, office, and primary suite. The office boasts custom cabinetry and pocket doors leading to the primary bedroom and a renovated en-suite bathroom with leathered marble countertops, wall sconces, more custom cabinetry, a walk-through closet, & a shower with a bench seat.The den offers a comfortable living space with a wood-burning fireplace, exposed beams, and access to the back porch. The updated kitchen features a large pantry and breakfast bar, with the mud area and laundry room nearby.An informal eating area showcases vaulted ceilings, exposed brick, and skylights. The Guest Quarters feature a private deck, full bath, and a second bedroom downstairs.Upstairs, you’ll find a sitting room and three bedrooms with ceiling fans, while the three upstairs fireplaces are not operational. A jack-and-jill bathroom connects two bedrooms. The fifth bedroom has a full en-suite bath.Outdoors, the 1.6-acre lot offers a workshop with electricity and window unit, a gardening shed, a pole barn, a gazebo with wild, climbing roses, a garden plot, & an orchard with apple, peach, and plum trees. The flower bed in the front circular drive hosts hyacinths & daylilies as well as over 600 tulip & daffodil bulbs, among other plants. Numerous updates and upgrades have been made to the home; ask your agent for a full list. The house is quite significant historically. It was originally built in 1838 by Roger Barton, an attorney who allegedly never lost a case. The columns holding up the front portico are said to have been salvaged from a now-demolished antebellum home named ”Cloverland” that stood 6 miles outside of Holly Springs. Additionally, during work in the dining room, the sellers found a Civil War era tunnel under the house that is believed to have connected to other buildings in town used to evade Union forces and for hiding valuables. The tunnel is now sealed and closed off. The following will stay with the property at no additional value: the peacock fireplace screens, the freezer in the laundry room, the playhouse shelf & wooden bed in pink bedroom upstairs, the gazebo, the metal arch off back porch, work surfaces & shelving in the workshop, & the zero-turn mower. This is a rare opportunity to own such a well-loved home steeped in history. Don’t miss your chance to be its next owner! Call your favorite agent & schedule your showing today.