Winchester, VA homes for sale & real estate

Winchester, VA Homes for Sale

Charming 1955 home offering timeless character, inviting curb appeal, and a versatile floor plan! This 3-bedroom, 2-full-bath home features one bedroom conveniently located on the main level, along with a dedicated office that provides a great space for working from home, hobbies, or additional flex space. One of the two full bathrooms is brand new, adding a fresh modern touch to this classic home.

Winchester, VA Homes for Sale

Your Next Chapter Starts Here! Space, style, flexibility, and a backyard made for entertaining — all tucked away on a quiet cul-de-sac in desirable Oakdale Crossing. This impressive 5-bedroom, 4-bathroom, three-level Colonial, with new roof (2026), delivers the kind of versatile space today’s buyers are looking for, with room to work from home, host friends, grow your household, or create the ultimate hangout zone. Start with the front wraparound porch, the perfect spot for morning coffee or winding down at the end of the day. Out back, the fun really begins: multiple composite decks with a pergola overlook a private, fully fenced yard backed by mature trees, creating your own o

Winchester, VA Homes for Sale

Garage space like this is hard to find. Set on 10.05 private acres in Deerfield Estates, this all-brick rancher is anchored by a five-bay detached garage (garage lifts do not convey) with full electric, a half bath, metal roof, and six garage door openers, plus a two-car attached garage. A separate two-story outbuilding adds even more flexibility with ceramic tile flooring and built-in cabinetry, making it well suited for hobbies, projects, storage, or additional workspace. An additional 8x10 shed conveys, and a whole-house generator adds valuable backup power. Mature trees surround the property and create a private setting across two parcels. Inside, hardwood flooring runs throughout the m

Winchester, VA Homes for Sale

Warm, elegant, and beautifully maintained, this 5-bedroom, 4.5-bath home offers gracious living in a desirable City of Winchester neighborhood with no HOA. Step into the spacious foyer, where refined crown molding and a striking staircase create a memorable first impression. Just beyond, a private office with built-in shelving and a cleverly concealed Murphy bed offers exceptional versatility, while the formal living room flows gracefully into a column-framed dining room designed for memorable gatherings. At the heart of the home, the bright and welcoming kitchen features an island cooktop and an adjoining breakfast area with double doors opening to a hardscaped patio - a lovely setting for