Steeped in history and timeless country charm, Homestead Farm dating back to 1782 and the namesake of Homestead Road is one of Tewksbury's most picturesque preserved equestrian estates. Set on twenty-six serene acres surrounded by thousands of acres of farmland in a valley of preserved land with equestrian trails, the property overlooks a stunning stream-fed pond with a waterfall and sweeping pastoral views. The historic stone barn features eight stalls, a tack room, an eighty-foot by one hundred forty-foot indoor arena with a ten-foot by twenty-five-foot viewing room, and fourteen outdoor paddocks, four of which have run-in sheds, a large three hundred foot by one hundred foot outdoor riding area, a round pen for lunging, creating an exceptional equestrian setting. The farmhouse blends historic character with inviting living spaces, including wide-plank pumpkin pine floors, three fireplaces, a formal dining room, and a sun-filled family room with walls of windows framing the pond and gardens. The spacious primary suite offers a soaking tub and walk-in closet. An oversized bluestone patio draped in wisteria provides a breathtaking setting for entertaining or quiet relaxation beside the pond that has been cherished by generations for two hundred forty-four years. In addition to the timeless farmhouse, there is a charming standalone flex space currently used as an artist's studio, featuring vaulted ceilings, original hand-hewn beams, and an oversized Palladian window overlooking acres of paddocks. A rare blend of heritage, craftsmanship, and equestrian excellence, Homestead Farm is a MUST SEE!