$323,974Average Value$230Average Price per Sq Ft19Homes For Sale
Life in wooded Winston, along the South Umpqua River
Most known for its Wildlife Safari and natural setting, Winston sits along the curve of the South Umpqua River, surrounded by forested landscapes. Just shy of 6,000 residents, Winston's small population and limited retail contribute to a slower pace of life and sense of community. Deleta Dickson, a Realtor with eXp Realty, who lives in a neighboring town, describes Winston's close connection, noting that many of her clients have moved here to be near family. Just 7 miles from the county seat in Roseburg, Dickson says that some have also chosen Winston for its Douglas County location and its direct route to the coast in Bandon, roughly 70 miles west. Eugene and Medford are within 80 miles.
The iconic “Welcome to Winston” sign greets visitors to this scenic town along the South Umpqua River.
Winston, nestled in Douglas County, offers rolling landscapes and a welcoming, close-knit community.
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Fishing, kayaking and more at Winston's parks
At Winston's Wildlife Safari, visitors can take a driving tour of the park, which houses over 500 animals and 80 species. On the town's southeastern side is Riverbend Park, named for being at the bend of the Umpqua River. It has a playground, skate park and picnic areas. People head there in the summer for a free concert series that starts in June and showcases the talent of regional and national artists. Winston Dillard County Park surrounds the Winston Library, offering another playground and basketball courts. Harold and Sid Nichols Park is home to a public boat ramp. "Everyone kind of has their special spot to fish and swim," Dickson says. "You can ride kayaks down [the river] or an inner tube in some places. We call it floating the river here." Prized catches in Winston are summer steelhead and rainbow trout that can reach 20 pounds. Roughly 40 miles north, Umpqua National Forest sprawls for nearly a million acres with trails leading past waterfalls.
Harold and Sid Nicholas Park runs along the South Umpqua River in Winston, Oregon.
The gateway to adventure—Winston’s Wildlife Safari offers a drive-through experience with diverse wildlife.
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Houses surrounded by mountains, some on acreage
Winston's homes are set within its rolling landscape, surrounded by mountains. "You're going to have the gamut of housing, from starter homes to high-end properties and everything in between," Dickson says. "The most common are single-level ranch homes." The median list price in Winston is around $370,000, but some properties exceed $1 million, while others are priced under $100,000. Homes with ample acreage or riverfront access fetch the highest prices. Lot sizes range from less than 10,000 square feet to over 20 acres. While most properties are single-family homes, manufactured dwellings also have a foothold here. Condos and townhouses are in limited supply. Winston also has some new construction. Plans are underway for Rolling Meadows, a 57-lot development that will span 11 acres on Winston's eastern side.
Many homes in the community are ranch-style, reflecting Winston’s relaxed pace of life.
New construction homes line the quiet streets of Winston.
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Winston's dining scene and local shopping spots
Shopping and dining in the area largely cluster around Southeast Main Street and Northwest Douglas Boulevard. Winston Diner & Drive-Thru serves burgers, milkshakes and sandwiches in a 1950s-style diner with checkerboard floors. Willee's Cafe and Spirits is one of the more popular spots during happy hour. Locals can satisfy their cravings for a slice at Abby's Legendary Pizza or tacos at Muchas Gracias. Exspresso's is the hometown coffee spot with a wide range of specialty drinks. Grocery Outlet sells a wide range of produce and pantry staples in town at discounted rates. Brosi's Sugartree Farms, east of Winston, is a U-Pick facility with a farm stand that's open daily. Nearby tasting rooms include Abacela Winery and Freed Estates Vineyard, less than 3 miles away.
Winston has more restaurants than retailers, but it does include a hardware store and a discount shop. "Roseberg has a Ross, a Walmart Supercenter and Marshalls, but we don't have a ton of shopping here either," Dickson says. "When we shop for school clothes, we drive an hour to Eugene or Medford."
Willie's Cafe is a popular spot for happy hour, along Highway 99 in Winston.
Grocery Outlet offers discounted produce and pantry staples in Winston.
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Education through Winston-Dillard School District
Students attend the Winston-Dillard School District. They may begin at McGovern Elementary School before filtering into Winston Middle School and Douglas High School. All of these schools earn C-minus ratings on Niche. The elementary school has a small student body, leading to a student-teacher ratio of 13-to-1.
Douglas High School earns a C-minus rating on Niche.
McGovern Elementary School has a student-teacher ratio of 13-to-1.
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Highway 99 offers picturesque routes through Winston
Southeast Main Street, or Highway 99, cuts through Winston. Travelers can tour the landscape on several scenic drives, including the Rogue-Umpqua Scenic Byway and the Pacific Coast Scenic Byway. Nicknamed "the waterfall highway," the byway follows rivers and cascading waters.
Local parks and ramps vulnerable to flooding
Flooding in the area can be a concern after heavy rainfall or snowmelt. Riverbend Park and the Harold and Sid Nichols Boat Ramp have both been affected.
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Photography Contributed By
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On average, homes in Winston, OR sell after 78 days on the market compared to the national average of 57 days. The median sale price for homes in Winston, OR over the last 12 months is $320,500, down 7% from the median home sale price over the previous 12 months.
OPEN HOUSE - Saturday May 16th 12:00pm - 2:00pm Schedule your private tour today of this adorable 4bd 2ba open floor plan home, located on a generous lot, with an extra deep garage and additional off-street parking for your RV or Boat. Just a 15-minute drive to Roseburg, close to local schools and just down the street from the Wildlife Safari.
Rare investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Property has already been approved to be partitioned as either 2 larger parcels or a 28 lot subdivision! Currently no HOA or CC&Rs! Utilities conveniently are available nearby ready to be connected. The 2 parcels are also listed separately. Make an offer today before one or all
Great investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Currently no HOA or CC&Rs! Property has already been approved to be partitioned as a larger parcel or a over a dozen lot subdivision! Utilities conveniently are available nearby ready to be connected. The other parcel is also listed separately. Or both properties are available
Unique investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Currently no HOA or CC&Rs! Property has already been approved to be partitioned as a larger parcel or a over a dozen lot subdivision! Utilities conveniently are available nearby ready to be connected. The other parcel is also listed separately. Or both properties are available
Welcome to 380 Sunnyside! This move-in-ready 3-bedroom, 2-bath home offers comfort, quality updates, and everyday convenience. Vaulted ceilings and peaceful territorial views create a bright, open feel from the moment you step inside. Recent upgrades include fresh interior paint, brand-new LVP flooring, and a newly built spacious deck, giving the home a modern look without the new construction
Take in breathtaking views of Umpqua Valley and the surrounding mountains from this spacious manufactured home located in a welcoming 55+ community. Unwind on the large covered front porch. Featuring a metal roof, double-pane vinyl windows, and a sturdy concrete block foundation, this home offers lasting durability. Stay comfortable year-round with the newer heat pump installed in 2022.
Mary GilbertKeller Williams Southern Oregon-Umpqua Valley
There’s something special about stepping into a home that’s never been lived in—where everything is fresh, thoughtfully designed, and ready for your story to begin. Welcome to 260 Logan St, a brand-new one-level home that blends modern comfort with effortless living. From the moment you walk in, you’ll appreciate the clean, cohesive feel of luxury vinyl plank flooring throughout—no carpet—paired
Mary GilbertKeller Williams Southern Oregon-Umpqua Valley
Opportunity awaits! Whether you’re a savvy investor seeking passive income, a large family looking for a multi-generational setup, or a single household wanting a home with the luxury of renting out additional units, this three-home property offers countless possibilities.Located on historic Brockway Road, the property spans .58 acres and is lined with mature trees and lush landscaping, creating
Mary GilbertKeller Williams Southern Oregon-Umpqua Valley
Great investment opportunity on a spacious 0.74-acre lot! This property features a 3-bedroom, 1-bath single-level home with approximately 1,250 sq ft of living space, plus a duplex on the same lot—offering excellent potential for rental income or multi-generational living. The main home includes a full basement, forced air heating, and public utilities. Situated on a level to gently sloped lot
Mary GilbertKeller Williams Southern Oregon-Umpqua Valley
Welcome to Your Like-New Custom Home in Winston, Oregon!Step inside this beautifully crafted home by Shelby & Miguelena Construction, where quality craftsmanship and thoughtful design are evident in every detail. The open-concept floor plan features soaring vaulted ceilings, beautiful flooring, and a warm, inviting layout that flows effortlessly for both everyday living and entertaining.At the
Mary GilbertKeller Williams Southern Oregon-Umpqua Valley
Affordable living in a quiet 55+ community! This cozy 1-bedroom, 1-bath manufactured home offers a functional layout and easy, low-maintenance living. The kitchen comes equipped with a free-standing range and refrigerator, both included in the sale. Located in a peaceful, well-kept neighborhood with a friendly community atmosphere. Conveniently situated near local amenities while maintaining a
Mary GilbertKeller Williams Southern Oregon-Umpqua Valley
Developable residential lot zoned R1, offering a gentle slope and utilities available including electricity, sewer, and water. Enjoy a pleasant view overlooking nearby vineyards in the valley, providing a peaceful setting for your future home. Conveniently located within driving distance to the Umpqua River and Wildlife Safari, offering access to outdoor recreation and local attractions. Great
Mary GilbertKeller Williams Southern Oregon-Umpqua Valley
27.31 acres to build your dream home either on top of the property or in the valley. City water is available, and other utilities are accessible via a recorded easement. In photos, red boundary lines are approximate and buyer is to perform due diligence. All showings are to be with a licensed realtor. Please make note that this property is a combination of only R66808 & R66885. 0 E. Willis Creek
A house with a history. 1895 Home with 5+ bedrooms and lots of charm. This home has been in the family for 50+ years. 5+ Bdrm home. Built in 1895. On the River. Close In. Bedrooms/Bonus: 2 Small bedrooms are in attic, three are on 2nd floor. There are three "extra" rooms on first floor that have been used in the past as an office, music room, master bedroom, playroom,
Large 4 Bedroom, 2 Bath downstairs apartment. Stove, refrigerator, dishwasher, garbage disposal, laundry hook ups included. Gas fireplace insert in a brick wall feature and baseboard heat in bedrooms. Large grassy common area (shared with 3 other units) yard maintenance is providedRental Terms:• 6-month lease required• Cats are negotiable with additional $500 security deposit per
2 bedroom 1 bathroom downstairs apartment in Winston. Sewer and garbage paid. Unit has baseboard heat, stove, refrigerator, dishwasher, and washer/dryer hook ups. Small, back patio off the kitchen. Off-street parking. Rental Terms:• 6-month lease required• No Pets• Renter’s insurance required throughout term of lease• Tenant Responsible for ElectricAvailable:
Dillard is a small community next to the South Umpqua River with less than 400 residents. The area is based around a logging mill, the Dillard Mill, and is home to several trucking and logging companies. “It’s a tiny town with one little convenience store and a post office,” says Emily Volk, a Realtor with Karen Volk Realty, who has been selling homes in the area for over two decades. Not much happens in Dillard, Volk says. There’s not much else here besides businesses, a church and single-family homes. The nearby city of Winston offers more amenities -- people can travel 2 miles across the South Umpqua River Bridge to reach grocery and clothing stores, gas stations, parks, restaurants and bars. Dillard tends to attract veterans and retirees, according to Neil Hummel, Broker/Owner of Neil Co. Real Estate who grew up in the Roseburg area. The community is a part of Douglas County, which has one of the largest veteran populations in Oregon at 10,000. The area’s climate is a big draw for people, Hummel says. “People are attracted to the area because there’s no extreme cold or hot weather,” he says.
Oregon 99, also known as Dillard Highway, helps people reach work in Winston. There is no public transportation offered in Dillard. The Roseburg Regional Airport is 11 miles away but doesn't offer domestic or international flights. The Eugune Airport only has domestic flights with seven airlines about an hour and a half away, while the Portland International Airport is roughly 3 hours away.
Dillard store and Deli is the only convenience store in town, open daily from 4 a.m. to 11 p.m. People visit Grocery Outlet on Douglas Boulevard for larger grocery hauls. The Village Shingletowne Antique is the main shopping destination in Dillard that sells antiques, but people can also head to the Bi-Mart Membership Discount Store. Carlos Restaurante serves Mexican dishes and seafood. Johnny's Drive-In & Diner is a traditional, retro-style spot with classic meals like burgers and fries. They’re also known for their milkshakes and offer dine-in, drive-up and walk-up-window service.
Dillard has no parks of its own, but neighbors can enjoy the outdoors in nearby Winston. Winston Dillard County Park has a playground, basketball courts, and a pavilion area for cookouts and picnics. Next door, the Winston Community Center is an event space, often hosting birthday parties and baby showers. People visit Riverbend Park for its skatepark, baseball fields, and playground. Since it’s so close to the river, it’s also a hot spot for fishing and swimming.
Potential homebuyers will find bungalows with decent-sized lawns. Properties are typically surrounded by trees and range between $50,000 and $200,000, depending on the number of bedrooms. Daily walks can be a bit difficult since most homes don’t lead to sidewalks. Most homes don’t have driveways either -- instead people make their own lots, where cars are parked next to properties.
Children can attend McGovern Elementary School, before advancing to Winston Middle School, which has after school activity nights where students can play games like checkers and UNO. Both schools earn a C-minus from Niche. Kids move on to Douglas High School, which receives a C and offers educational tours throughout the country, where they can do hands-on activities and learn from professionals in their specific subject field. Students are scheduled to visit Scotland and Ireland during the 2024-25 school year. There are no private schools in the area, but there is one church, the Dillard Church of God.
With all the open land in Dillard, a couple of vineyards have opened throughout the years, which include Freed Estate Vineyards and Abacela Winery. These family-owned vineyards offer exclusive wine clubs, membership events and public wine tastings. Riverbend Live! is an annual concert series at Riverbend Park that starts on the last Friday in June and lasts six weeks. The park also hosts a Fourth of July festival, and the Winston-Dillard Melon Festival, a three-day event in September that includes a car show, barbecue vendors, mud volleyball, live music and a lot of watermelons. The Douglas County Fair is another popular event that welcomes hundreds of residents yearly.
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Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
