Set against the dramatic backdrop of the Kittatinny Ridge at the base of North Mountain, Waggoners Gap this extraordinary historic estate offers a once-in-a-generation opportunity to own one of Cumberland Valley's most storied properties. Known as the “Abraham Waggoner House,” this remarkable limestone residence traces its origins back to the late 1700s and seamlessly blends centuries of Pennsylvania history with thoughtful modern restoration across nearly 7 breathtaking acres. Originally established around 1780 by Revolutionary War veteran and blacksmith Hans Jacob Waggoner, the original stone dwelling served as a rare and enduring landmark during America's earliest years. In 1817, his son Abraham Waggoner expanded the property with the grand Federal-style mansion home, originally operating as a bustling inn and wagon stand for travelers journeying through the mountain pass now famously known as Waggoners Gap. Rich with heritage and architectural significance, the estate remains a physical testament to early American craftsmanship, commerce, and enduring legacy. Today, the connected residences offer over 4,600 square feet of beautifully preserved and thoughtfully updated living space, where historic character and modern comfort exist in perfect harmony. Deep window wells, exposed beams, original hardwood flooring, soaring ceilings, and multiple massive stone fireplaces create an atmosphere that feels both timeless and unforgettable. The main residence features five spacious bedrooms and three brand-new full bathrooms, including a first-floor primary suite with a newly renovated ensuite bath. The stunning new kitchen showcases exposed-beam cathedral ceilings and opens into expansive gathering spaces including a large family room and recreation room designed for entertaining, relaxing, and making memories for generations to come. The second floor offers additional bedrooms, a large laundry room, and a charming balcony overlooking both North and South Mountain, while the third floor provides additional bedrooms, recreation space, and a finished loft filled with warmth and character. Connected to the main home is the original 1780 stone house - an incredibly rare preservation of early American architecture. With exposed beams, wood floors, a massive stone fireplace, and its own finished loft, this space offers endless possibilities as a guest house, artist studio, private retreat, office, or multigenerational living quarters. A new metal roof installed in 2024 complements the careful stewardship of the home's historic integrity. Outside, the grounds are equally captivating. Nearly seven acres of pasture and woodland create a private mountain retreat unlike anything else on the market. A fenced pasture, year-round stream, fenced swimming pool, oversized two-car garage with workshop, attached four-stall barn, and additional fenced pen ideal for hobby farming or chickens complete the estate. Recent updates to the garage and barn include new siding and roofing in 2025. Perfectly positioned beneath Hawk Watch and surrounded by the beauty of the Cumberland Valley countryside, this property offers the rare chance to own not simply a home, but a meaningful piece of Pennsylvania history - lovingly restored, beautifully updated, and ready for its next chapter.