25

Winston, OR Houses for Sale

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  • /41

    $650,000

    • 3 Beds
    • 2 Baths
    • 2,600 Sq Ft

    1260 Ireland Rd, Winston, OR 97496

    Country Retreat on 10.02 acres. The Perfect blend of luxury and privacy in southern Oregon. This custom built 2600 square ft. home offers 3 bedrooms and 2 bathrooms. Step inside to an inviting open floor plan featuring vaulted ceilings and elegant finishes. The gourmet kitchen is a chef's dream, complete with premium appliances, custom cabinets and s spacious island perfect for hosting. The

    Agent Photo

    Daniel Siler

    Engel & Volkers West Portland

    (458) 232-4863

    1260 Ireland Rd, Winston, OR 97496
  • /37

    $410,000

    • 3 Beds
    • 2 Baths
    • 1,554 Sq Ft

    360 NE Rose Ridge Dr, Winston, OR 97496

    Beautiful 3BD/2BTH home in Winston’s sought-after Rolling Meadows neighborhood! Built by Avery Homes in 2021, this one-level residence feels "like new" and is completely move-in ready. Enjoy an open-concept layout with durable LVP flooring, quartz countertops, and a bright, spacious living area perfect for everyday activities and entertaining. Energy-efficient solar panels installed in July 2024

    Aaron Cherry Oregon Life Homes

    360 NE Rose Ridge Dr, Winston, OR 97496
  • /46

    $469,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,770 Sq Ft

    113 Citation Ct, Winston, OR 97496

    Welcome to 113 Citation Ct, Winston, OR 97496! This brand-new home in the desirable Lookingglass Creek Estates offers modern style and quality craftsmanship throughout. Enjoy a bright, open layout with vaulted ceilings and upscale finishes, including soft-close cabinetry, sleek quartz countertops, a spacious pantry, and durable luxury vinyl plank flooring. The private primary suite features a

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    113 Citation Ct, Winston, OR 97496
  • /39

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,310 Sq Ft

    441 NW Galaxy Dr, Winston, OR 97496

    Beautiful home overlooking the city w/panoramic views of surrounding mountains and valleys. Feels like a private oasis with multiple decks and thoughtfully designated areas for entertaining or relaxation. Enhancing the homes appeal, is a fully finished and heated shop w/ vaulted ceilings, skylight and wood beams seamlessly attached to the garage. The garage is also fully finished w/ heating &

    Nichole Sharman Works Real Estate

    441 NW Galaxy Dr, Winston, OR 97496
  • /48

    $670,000

    • 4 Beds
    • 2 Baths
    • 1,920 Sq Ft

    1950 Byron Creek Rd, Winston, OR 97496

    End of the road Privacy on 12+ acres. This one has it all and borders BLM! This 2008, 1920sft, custom, stickbuilt home is 1-level with gorgeous kitchen, custom cabinets, hardwood floors & granite countertops + pantry. The soaring ceilings add to the appeal. 4 spacious bedrooms. Covered patio for outdoor barbecues. Comes with a 1500 sq ft shop is 50 x 30 with 16' eaves, a break room and full bath!

    Veronica Gillespie eXp Realty, LLC

    1950 Byron Creek Rd, Winston, OR 97496
  • /48

    $760,000

    • 4 Beds
    • 2.5 Baths
    • 2,362 Sq Ft

    1068 Rice Creek Rd, Winston, OR 97496

    Gated 8.5 acres country living, fenced X Fenced, beautiful ranch style updated home. Newer roof, newer paint in and out, gourmet kitchen w/DBL ovens & cooking pantry, large living room with fireplace, huge primary bedroom with walk in closet 2 headed shower & 3 nice sized bedrooms, one bedroom can be use for office space. 36x40 Shop with office & 1/2 bath & extra garage with tool room. City

    Joan Smith G. Stiles Realty

    1068 Rice Creek Rd, Winston, OR 97496
  • /32

    $590,000

    • 4 Beds
    • 3 Baths
    • 2,660 Sq Ft

    102 Sarah Bear Ln, Winston, OR 97496

    Stately quality 4 br 3 bath home, real wood floors, 2 gas fireplaces, central vac, top quality custom elegant crown molding. Formal dining, gourmet kitchen, over sized gazebo/pergola, colored stamped concrete, sprinkler system, fenced manicured private backyard with raised beds. Has new astro turf for low maintenance, covered patio. The gourmet kitchen has granite, pantry, new gas appliances,

    Valynn Currie Currieco Real Estate

    102 Sarah Bear Ln, Winston, OR 97496
  • /47

    $649,900

    • 4 Beds
    • 2.5 Baths
    • 2,144 Sq Ft

    490 Dawson Dr, Winston, OR 97496

    Escape to the privacy of Byron Creek Estates, where this beautiful 4-bedroom, 2.5-bath home sits on 5 serene acres just outside Winston! Thoughtfully designed with vaulted ceilings and abundant natural light, the home has a fresh interior, featuring new laminate flooring in the main living area, shampooed carpets, and new paint. The spacious master suite with vaulted ceilings upstairs is a

    Anthony Beckham Different Better Real Estate

    490 Dawson Dr, Winston, OR 97496
  • /48

    $565,000

    • 3 Beds
    • 2 Baths
    • 2,167 Sq Ft

    7941 Upper Olalla Rd, Winston, OR 97496

    Beautiful 5.01 acre property with 2007 rebuilt home! Lots of flat ground for vegetable/flower garden. Fenced and cross fenced. Good well and 2 - 1200 gallon holding tanks. New water softener. Year-round creek. Large drive-thru shop with 3 - 12ft doors, 3 stall barn, and spring fed holding tanks plumbed to barn. Huge metal building for many uses. Plus, 2 sheds and 1 fort. Lots of room for animals

    Carol Williams The Neil Company Real Estate

    7941 Upper Olalla Rd, Winston, OR 97496
  • /32

    $499,500

    • 3 Beds
    • 2 Baths
    • 2,186 Sq Ft

    240 Wil Way, Winston, OR 97496

    Welcome to the highly desirable neighborhood of Safari Estates. This custom built 3-bedroom, 2 bath home offers stunning views of the rolling forested hills and is in the heart of wine country. The expansive living room is flooded with natural light, showcasing the breathtaking views through large windows that seamlessly connect the indoors to the outdoor patio space. The open-concept with

    Jacob Sanchez Next Generation Real Estate LLC

    240 Wil Way, Winston, OR 97496
  • /35

    $469,000

    • 4 Beds
    • 2 Baths
    • 1,994 Sq Ft

    197 Wil Way, Winston, OR 97496

    Don't miss this beautifully maintained Custom one level home with 4 bedrooms and 2 bath in Safari Estates. Vaulted ceilings in living room and beautiful mountain east views. Floor plan is open with plenty of natural light. Gas fireplace for those cozy days in the living room. Laminate flooring through out living space with carpet in bedrooms for warmth. Tile flooring in bathrooms with tile shower

    Nancy Wood Oregon Life Homes

    197 Wil Way, Winston, OR 97496
  • /6

    $359,000

    • 3 Beds
    • 2 Baths
    • 1,257 Sq Ft

    185 Lebleu Ln, Winston, OR 97496

    Welcome home to this well maintained single-story home with a modern floorplan, featuring an inviting open-concept layout designed for both comfort and privacy. The spacious primary bedroom includes an attached bathroom, offering a private retreat. The living room features a gas fireplace, perfect for relaxing evenings. Step outside to enjoy unrestricted views of nature from the backyard,

    Kurt Delahooke Keller Williams Realty Eugene and Springfield

    185 Lebleu Ln, Winston, OR 97496
  • /47

    $389,900

    • 3 Beds
    • 1 Bath
    • 1,434 Sq Ft

    10 SE Kegler Ave, Winston, OR 97496

    Set on a full acre at the edge of town, this property blends flexibility, functionality, and a 1,200 sq ft shop that’s hard to ignore! The 3-bedroom, 1-bath home includes an oversized living room with exposed wood accents and rustic-style posts that bring a bit of texture and charm. Heating and cooling are handled with ductless systems, and there’s a gas fireplace to keep things cozy. The kitchen

    Anthony Beckham Different Better Real Estate

    10 SE Kegler Ave, Winston, OR 97496
  • /28

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,592 Sq Ft

    140 Teresa Ln, Winston, OR 97496

    This modern, beautiful home is located in the highly sought-after Winston neighborhood. The home has been recently remodeled down to the studs and includes brand new HVAC, new appliances, and new roof. Step inside to find luxury vinyl plank flooring, recessed lighting, and soaring vaulted ceilings, and an abundance of windows that create a spacious and inviting atmosphere. The open-concept

    Jason Mann J Mann Realty

    140 Teresa Ln, Winston, OR 97496
  • /47

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,374 Sq Ft

    231 NE Darrell Ave, Winston, OR 97496

    Great location with a custom built one level home located on .39 of an acre at the end of the road in Winston with City Services! Home built in 1981 with approximately 1,374 square feet, 3 bedrooms and 2 full bathrooms, primary bedroom and bathroom has a walk-in closet and slider door to deck, nice Kitchen with oodles of oak cabinets, lots of counter space, plus a pantry, Living room has

    Cynthia Johnson Johnson Group Real Estate, LLC

    231 NE Darrell Ave, Winston, OR 97496
  • /41

    $870,000

    • 4 Beds
    • 3 Baths
    • 3,000 Sq Ft

    375 Porter Creek Rd, Winston, OR 97496

    Discover the perfect blend of vineyard lifestyle and modern comfort in this beautifully updated 41-acre estate, nestled in the heart of Oregon’s Umpqua Valley AVA. Surrounded by timber, a year-round creek, and a seasonal pond, this scenic retreat offers privacy, natural beauty, and endless potential.At the heart of the property is a spacious 3,000 sq ft home featuring four large bedrooms and

    Lorrie Normann Triple Oaks Realty LLC

    375 Porter Creek Rd, Winston, OR 97496
  • /23

    $294,900

    • 3 Beds
    • 1 Bath
    • 1,668 Sq Ft

    551 NW T St, Winston, OR 97496

    Charming, beautifully updated, move-in-ready home in Winston! The perfect blend of turn key and affordability. Fresh, modern flooring, kitchen, bath, light fixtures and fun finishes give this home its clean aesthetic while the lovely fireplace and mid century details add warmth and character. New roof and so much more! Don’t miss this gem!

    Bob Lamonte Lamonte Real Estate Professionals

    551 NW T St, Winston, OR 97496
  • /39

    $345,000

    • 3 Beds
    • 2 Baths
    • 1,835 Sq Ft

    151 Sherry St, Winston, OR 97496

    Step into this charming 1965 Ranch-style home, nestled in a peaceful neighborhood on a generous double lot in the heart of Winston, Oregon. With 3 bedrooms, 1.5 bathrooms, and a large, fully fenced corner lot, this property offers both privacy and convenience. This home boasts ample storage space throughout, with built-in shelving and closets to keep your living areas tidy. The cozy and airy

    RaNae Sams Oregon Life Homes

    151 Sherry St, Winston, OR 97496
  • /29

    $279,400

    • 3 Beds
    • 1 Bath
    • 1,005 Sq Ft

    520 SE Dawna Ct, Winston, OR 97496

    Take advantage of a fantastic opportunity- sellers are offering a credit to the buyer, which can be used towards closing costs or even a rate buy-down! Conveniently located just a few blocks from Winston Middle School, this home offers 3 bedrooms, 1 bathroom and updates including laminate flooring throughout and a recent heating and air conditioning system. Outside offers an attached garage,

    Ashley Oberman Oregon Life Homes

    520 SE Dawna Ct, Winston, OR 97496
  • /9

    $150,000

    • 2 Beds
    • 1 Bath
    • 1,012 Sq Ft

    250 SW Ford Ave, Winston, OR 97496

    Newer Roof nice sized lot in an established neighborhood in Winston, OR. This Home is looking for a craftsman to turn it into its better self. The house is very Livable but non-permitted work has been done. "NOT FINACEABLE" with traditional terms, maybe a hard money loan. Call today for an appointment to visit with your investor or contractor.

    Dawn Trapalis Harcourts Integrity Team Real Estate Services, LLC.

    250 SW Ford Ave, Winston, OR 97496
  • /14

    $199,999

    • 2 Beds
    • 1 Bath
    • 735 Sq Ft

    110 SE Darrell Ave, Winston, OR 97496

    YOU WON'T WANT TO MISS THIS OPPORTUNITY. Cute updated 2 bedroom home with small utility room. Kitchen with appliances. Updated hot water heater, flooring, interior and exterior paint. Living room offers gas heater and a front bonus area. Partially fenced yard with garden shed in back. Nice corner lot with driveway. Call for your showing today!

    Lacey Williams Trueblood Real Estate

    110 SE Darrell Ave, Winston, OR 97496
  • /48

    $749,000

    • 3 Beds
    • 2.5 Baths
    • 1,845 Sq Ft

    1470 E Willis Creek Rd, Winston, OR 97496

    PRICE IMPROVEMENT! Nestled on 90 acres of private land, this stunning 3-bedroom, 2.5-bath log home offers the perfect retreat for those seeking tranquility and connection with nature. The main home is a masterpiece of rustic craftsmanship, featuring soaring vaulted ceilings, and large windows that bathe the living spaces in natural light. A cozy wood stove anchors the open concept living and

    Rhonda Marshall Knipe Realty ERA Powered

    1470 E Willis Creek Rd, Winston, OR 97496
  • /45

    $315,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,318 Sq Ft

    180 SE Darrell Ave, Winston, OR 97496

    Brand New Construction in Winston! Welcome to 180 SE Darrell Ave., a new 3-bedroom, 2-bathroom home offering modern finishes throughout. This move-in ready home features an open floor plan with seamless flow between the kitchen, dining, and living areas—perfect for both entertaining and everyday living. Enjoy cooking in the stylish kitchen with stainless steel appliances, quartz countertops, and

    Jennifer Kramer RE/MAX Integrity

    180 SE Darrell Ave, Winston, OR 97496
  • /43

    $310,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft

    200 SE Darrell Ave, Winston, OR 97496

    Welcome to your brand-new single level home! This beautifully designed residence features an open floor plan that seamlessly connects the spacious living, dining, and kitchen areas—perfect for both everyday living and entertaining. The kitchen features sleek quartz countertops, stainless steel appliances, and ample cabinetry. Luxury vinyl plank flooring flows throughout the main living spaces,

    Jennifer Kramer RE/MAX Integrity

    200 SE Darrell Ave, Winston, OR 97496
  • /48

    $749,000

    • 4 Beds
    • 2 Baths
    • 2,240 Sq Ft

    411 Woodland Dr, Roseburg, OR 97471

    End of road privacy in a quiet setting, this great two-story ranch-style home offers an unparalleled lifestyle with breathtaking views of the renowned Abacela Vineyard! Imagine waking up every day to the gentle beauty of the surrounding landscape, where the flowing waters of Lookingglass Creek add to the peaceful ambiance. The property features creek frontage with coveted irrigation rights,

    Nataly Mattox RE/MAX Integrity

    411 Woodland Dr, Roseburg, OR 97471

Why Live in Winston

Winston, a neighborhood along the South Umpqua River, is known for its natural setting and the popular Wildlife Safari, which features over 500 animals and 80 species. With a population of just under 6,000, Winston offers a slower pace of life and a strong sense of community. The area is surrounded by forested landscapes and is 7 miles from Roseburg, with Eugene and Medford within 80 miles. Local attractions include Riverbend Park, which has a playground, skate park, and picnic areas, and hosts a free concert series in the summer. Winston Dillard County Park and Harold and Sid Nichols Park provide additional recreational opportunities, including fishing, kayaking, and a public boat ramp. Housing in Winston ranges from starter homes to high-end properties, with single-level ranch homes being the most common. Some homes feature ample acreage or riverfront access. The dining scene is centered around Southeast Main Street and Northwest Douglas Boulevard, with options like Winston Diner & Drive-Thru, Willee's Cafe and Spirits, and Abby's Legendary Pizza. Shopping is limited, but essentials can be found at Grocery Outlet and Brosi's Sugartree Farms. The Winston-Dillard School District serves the area, though schools have average ratings. Highway 99 offers scenic routes through Winston, including the Rogue-Umpqua Scenic Byway. Flooding can be a concern in local parks and boat ramps after heavy rainfall or snowmelt.

Home Trends in Winston, OR

Housing Trends

Median Sale Price
$346,125
Median Single Family Sale Price
$353,000
Average Price Per Sq Ft
$245
Number of Homes for Sale
25
Last 12 months Home Sales
78
Months of Supply
3.80
Median List Price
$369,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
2%
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