Spanning 31.84 contiguous acres across two parcels, this estate pairs a custom 2010 main residence with guest suite and 2008 three-bay barn on a 30.21-acre tract with a private two-bedroom guest cottage on the adjacent 1.63-acre lot. The primary acreage is heavily forested with established Black Walnuts, Oak, Cherry and various other species with an active planting of an additional variety of trees. This exceptional property is secured by an environmental conservation easement, ensuring its wooded grounds, historic views, and vital natural resources remain undisturbed and provide unparalleled privacy. In addition, multiple properties adjacent are also protected in various easements. For the discerning buyer, this designation offers more than just the peace of mind that comes with a protected boundary; it provides a unique financial advantage through potential estate tax benefits and preferential property tax assessments. A masterclass in eco-conscious luxury, this Shepherdstown estate sets the gold standard for sustainable living. Engineered from the ground up with Structural Insulated Panels (SIPS) providing a superior thermal envelope and a sophisticated palette of reclaimed materials, including flooring milled from the property’s own timber. This property masterfully balances architectural luxury with a pioneering environmental conscience, utilizing a rainwater harvesting system and Energy Star technology to offer a lifestyle of unrivaled efficiency and versatility. Designed for seamless indoor-outdoor living, this 4-bedroom, 3.5-bath modern craftsman flows effortlessly from the entryway through the living room and custom kitchen to a sprawling flagstone patio, pergola, and garden. Centrally positioned, a masonry heater acts as both an architectural anchor and a high-efficiency heat source, strategically bisecting the floor plan to radiate consistent warmth across both floors. Unlike a traditional fireplace, it captures heat from a single fire and slowly releases it over 12 to 24 hours to maintain a perfectly stabilized climate. An oversized two-car garage completes the estate, topped by a private 600-square-foot, one-bedroom apartment with its own kitchenette and exterior entrance. Beyond the main residence, a 24'x38' clear-span barn provides expansive utility, featuring three bays and a post-free interior ideal for heavy equipment or a workshop, plus a full second-story loft. The property also includes a separate 1.63-acre currently commercially zoned parcel featuring a versatile 1,000-square-foot carriage house used as a rental property. If used as a true guest house, the parcel would revert to agricultural zoning due to the conservation easement. While it was constructed in 1977, this secondary residence has undergone a series of comprehensive modernization, most recently in 2018, to create a sophisticated living space above a dedicated three-car garage. The interior is defined by hardwood flooring, custom cabinetry with tile accents, and built-in shelving, while the primary bath offers the high-end comfort of radiant heat. With a full bathroom on each level, a main-floor laundry, and two upper-level bedrooms, this parcel represents a turnkey income opportunity or a flexible residential retreat for family and friends. Set on a generous parcel, the home is bordered by mature hardwoods and features a network of private, sun-dappled trails that meander through the woods. The grounds offer an exceptional vision of outdoor living and environmental stewardship. For the gardening enthusiast, a substantial, deer-fenced garden plot stands ready for seasonal production, complemented by meticulously mulched perennial beds and stacked-stone retaining walls. Just beyond the property line, the vibrant spirit of Shepherdstown awaits. This historic enclave seamlessly blends its deep-rooted heritage with the energy of a thriving University town, anchored by the cultural events, parades, and seasonal celebrations.