Perfectly positioned along Charles Town Pike on 3.5 private acres backing to a picturesque 20-acre horse farm, this custom-built estate offers a rare combination of craftsmanship, setting, and income potential in western Loudoun County. The main residence delivers over 3,100 square feet of character-rich living space, thoughtfully designed and built with intention, and is complemented by a charming guest cottage that currently operates as a popular short-term rental with an established booking history. The property's additional structures set it apart. An expansive barn with a finished tasting room, a detached flex building, dual entrances, and parking for 50+ vehicles give the next owner room to live, work, entertain, and grow. Approximately half an acre remains under vine, a nod to the property's winery heritage and a distinctive feature of the grounds. Outdoor living is where the property shines: a 1,200 square foot deck, fire pit area, and multiple gathering spaces overlook the pastoral setting, creating an exceptional backdrop for everyday living and entertaining. Recent improvements include new septic systems, updated HVAC, solar lighting, and infrastructure upgrades throughout. Zoned A-3, the property falls within a district that accommodates a range of residential, agricultural, and rural business uses; buyers should verify intended uses with Loudoun County. Whether you are seeking a one-of-a-kind primary residence with built-in rental income or a private estate with room for your vision, this property offers lifestyle and flexibility that rarely come to market in one of Northern Virginia's most sought-after settings.