Welcome to 2181 Whippoorwill Road, a private 7.7-acre retreat located near the Butler's Crossing shopping area, but in the highly sought-after North Oconee High School district. This 4-bedroom, 3.5 bathroom offers a primary bedroom & en-suite, with walk-in closet, on the main level, and an additional primary bedroom & en-suite, with walk-in closet and bonus room, with 2 more bedrooms & full bath upstairs ( both upstairs bathrooms were remodeled in 2024). It blends timeless character with thoughtful updates across 2,600+ square feet of living space. The long wooded driveway leads to a welcoming front porch that sets the tone for peaceful country living. Inside, a soaring two story family room creates a warm, inviting space anchored by a classic Fisher wood burning stove. The remodeled kitchen, which was completed in 2020, is a true showpiece, featuring quartz countertops, dual sinks, premium appliances, and a large central island ready for casual breakfasts or there is a formal dining room for full-on entertaining. A powder room & large laundry area are also on the main. With multiple heating/cooling sources including a wood stove and central HVAC, the home is designed for year-round comfort. Youll also find a large screened in porch with a jet soaking tub, and a 2-car garage-everything you need to relax, unwind, and spread out. With mature trees, quiet surroundings, and just a short drive to Watkinsville or Athens, this property offers the best of both worlds: peaceful seclusion and modern convenience.