OAKLAND, circa 1790, is a distinctive 18-acre country estate with views of the Blue Ridge about 90 minutes from D.C. A gracious approach introduces the character rich 4-bedroom main residence. The property unfolds with exceptional infrastructure and additional living spaces, with thoughtful updates throughout, offering up to 6 bedrooms in all for multi-generational living, equestrian pursuits, or a weekend escape. Access to I-66 is quick. The original 18th-century portion of the stone-and-stucco home features a broad front porch, wide-plank hardwood floors, a gracefully curved staircase and tall ceilings. A fireplace anchors the library, while both the library and dining room feature custom built-in cabinetry. A hallway lined with exposed logs creates a striking transition between old and new, as the home opens to oversized windows and walls of glass that fill the interiors with natural light and frame mountain views. The heart of the home is a generously scaled renovated kitchen with a massive center island for gathering. The adjoining great room extends naturally outdoors through French doors to the rear veranda, pool and pavilion, with views stretching across the stables and pastures. The upstairs primary suite is impressive in both scale and amenities. A wall of windows captures the property’s best view, also enjoyed from a private deck. Two separate full bathrooms with heated floors and two spacious walk-in closets with custom built-in systems provide rare comfort and privacy, while a dedicated wellness and fitness room with hot tub completes this exceptional retreat. A large ensuite bedroom, two additional bedrooms, a full bath, and conveniently located laundry room complete the upper level. Oakland offers an unparalleled outdoors life. Three sets of French doors open to a veranda, ideal for dining al fresco and entertaining. Steps away, the saltwater pool and spa are connected by a waterfall feature, while a pool pavilion with gas fireplace and half bath creates a relaxing destination. Surrounding mature landscaping offers natural privacy. A covered breezeway connects the main house to a two-car garage. Above the garage is a bright spacious suite, flexible enough for a home office, creative studio, gym, homeschooling space, or private guest quarters. For the equestrian, a beautifully built 6-stall center-aisle stable will suit both the serious and recreational rider. The large rubber-matted stalls with exterior Dutch doors are complemented by a wash stall, heated tack room, and convenient access to the surrounding fields. Four-board fencing encloses two large pastures with substantial run-in sheds, along with a smaller pasture and separate paddock or grass riding area. Adjoining the stable is a newly renovated and expanded one-bedroom, one-bath apartment—ideal for extended family, guests, a caretaker or farm manager, or potential rental use. An attached deep 3-bay garage accommodates up to six vehicles, offering rare space for a car collection, equipment and storage, hobbies, or workshop use. A private helicopter hanger has been recently transformed into a memorable setting for a wedding, its concrete floor, industrial lighting and newly added oversized windows make the space adaptable and welcoming for future events. Presiding over the property is Oakland’s old bank barn. Grand in scale and rich with character, it remains functional for hay storage or livestock, while its rustic beauty whispers history. Oakland celebrates Virginia at its best. A short 5 miles to I-66. 90 minutes to Washington DC. 20 minutes to Winchester.