Homes with virtual tours for Sale in Winston, OR

Home with Virtual Tour for sale in Winston, OR:

Welcome to your new wilderness retreat!Perched atop a hill and backed by 393 acres of BLM land, this property offers the perfect blend of privacy, exploration, and functionality. Surrounded by trees, you’ll feel miles from anywhere — yet you’re only 10 miles from Roseburg. The well-maintained grounds give off a peaceful, park-like ambience from the moment you arrive. While the property slopes in some areas, there’s plenty of usable land to fit your needs. Among the trees are four seasonal ponds, which could be lined to maximize your water supply for irrigation. At the top of the driveway, you’ll find an impressive 60x60 shop — ideal for mechanics, hobbyis

Home with Virtual Tour for sale in Winston, OR:

Over 92 acres privately situated in beautiful Sibold Canyon. This spacious 4bd/3bth home offers vaulted ceilings, generous living areas, and a large primary suite. Interior repair is needed in the kitchen/dining area due to a past plumbing leak - priced accordingly. Outdoor living features covered porches, an expansive deck, hot tub, garden beds, fruit trees, and workshop. A 23x35 three-car garage plus multiple outbuildings provide excellent space for equipment and projects. Seasonal Porter Creek, trails, access roads, and abundant wildlife create a peaceful natural setting. Viewing by appt only. Adjacent buildable 16+ acres also available MLS #756380943 - purchase separately or together. C

Home with Virtual Tour for sale in Winston, OR:

Welcome to this 3-bedroom, 2-bathroom home with VIEWS in the serene Littlebrook gated 55+ community, located on the scenic South Umpqua River. This home offers a peaceful retreat overlooking the pasture, river and surrounding hills. The open floor plan features soaring vaulted ceilings, hardwood floors, and large windows that flood the space with natural light. The spacious kitchen has a large island, and abundant cabinetry. A window over the sink offers views of the surrounding hills. Step onto the covered back deck off the living room, where you can relax and enjoy the peaceful views. The primary suite includes double sinks, a spa tub and a walk-in shower. Residents have access to 21 acre

Home with Virtual Tour for sale in Winston, OR:

Welcome to Lookingglass Vineyard, a remarkable 142.94-acre estate nestled in the highly sought-after South Valley Wine Loop of the renowned Umpqua Valley AVA. This established and producing vineyard features 99.94± acres planted in Pinot Noir and an additional 1/2-acre parcel with other select varietals, offering an exceptional opportunity for both lifestyle and investment. The vineyard is fully equipped with drip irrigation, steel end posts, and wind machines, ensuring optimal fruit quality and efficiency. The property also includes a historic barn, large shop, oversized detached two-car garage, and a storage building, all set behind a gated entrance for privacy and security. Irriga

Home with Virtual Tour for sale in Winston, OR:

Just a short walk from Sunnyslope Elementary, this 3-bedroom, 2-bath home offers the perfect mix of comfort, space, and functionality. The detached, fully permitted 25x35 shop/garage is equipped with electrical and plumbing, and features an upstairs space that could potentially be transformed into guest quarters, an office, or a creative studio. Inside, you'll find solid hardwood floors throughout much of the home, paired with fresh carpet in the dining area, primary bedroom, and third bedroom, along with new flooring in the primary bathroom. The roof is approximately 10 years old, offering peace of mind for years to come. Step outside to enjoy your fully fenced backyard filled with pear, a

Home with Virtual Tour for sale in Winston, OR:

Be sure to come check out this adorable turn key home!!Tucked at the end of a quiet cul-de-sac, this charming single-level home combines comfort, style, and smart updates. The open layout offers three bedrooms, two bathrooms, and a bright, modern feel throughout. The kitchen features custom wood cabinets and flows easily into the spacious living area—perfect for everyday living or entertaining. Recent upgrades include exterior paint (2021), a new roof and deck awning (April 2025), new Trex deck (April 2025), new heat pump and furnace (2022), luxury vinyl plank flooring (2022), new water heater (2021), and a marble vanity. Step outside to a private, fenced backyard with a covered porch