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Winston, OR 1-Story Homes for Sale

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  • /83

    $735,000

    $50K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,722 Sq Ft

    9114 Old Highway 99 S, Winston, OR 97496

    Escape to the peace and beauty of rural Oregon with this beautifully remodeled country retreat set on 5.4 usable acres of fenced pastureland. Offering the perfect blend of modern comfort and small-acreage functionality, this stunning single-level home features 2,722 sq. ft. with 3 bedrooms, 3 full baths, and a versatile flex space ideal for a home office or hobby room. Each bedroom includes its

    Agent Photo

    Kristina Scott

    Umpqua Legacy Realty LLC

    9114 Old Highway 99 S, Winston, OR 97496
  • /44

    $499,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,576 Sq Ft

    2581 NW Brockway Rd, Winston, OR 97496

    This beautifully crafted new construction home offers 2,576 square feet with 3 bedrooms and 2.5 bathrooms, thoughtfully designed with quality finishes and modern comfort throughout. The open-concept floor plan features vaulted ceilings, abundant natural light, and recessed lighting, creating a bright and inviting living space. The kitchen is designed for both function and style with a large

    Agent Photo

    Tyler Head

    Turning Point Realty Group

    2581 NW Brockway Rd, Winston, OR 97496
  • /41

    $499,900

    New Construction $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,089 Sq Ft

    160 Wil Way, Winston, OR 97496

    New Home by JW Construction Inc. This beautiful one-level home offers just over 2,000 square feet with three bedrooms and two and a half bathrooms. The open great room features vaulted ceilings, luxury vinyl plank flooring, recessed lighting, and a gas fireplace. A large sliding door opens to an expansive deck, perfect for entertaining or relaxing. The kitchen is designed for both style and

    Agent Photo

    Tyler Head

    Turning Point Realty Group

    160 Wil Way, Winston, OR 97496
  • /36

    $459,000

    • 3 Beds
    • 1 Bath
    • 1,250 Sq Ft

    311 SE Grape Ave, Winston, OR 97496

    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 Gilbert Keller Williams Southern Oregon-Umpqua Valley

    311 SE Grape Ave, Winston, OR 97496
  • /38

    $409,900

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    623 SE Garden Way Dr, Winston, OR 97496

    Welcome to 623 SE Garden Way Dr, Winston, OR, where modern style, comfort, and convenience come together in one beautifully maintained single-level home. Built in 2019, this 3-bedroom, 2-bath residence offers an inviting open-concept layout with soaring vaulted ceilings and durable luxury vinyl flooring throughout, creating a bright, stylish, and low-maintenance living space. The well-appointed

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    623 SE Garden Way Dr, Winston, OR 97496
  • /48

    $366,000

    $19K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,613 Sq Ft

    186 Woodduck St, Winston, OR 97496

    Well-maintained home in a quiet neighborhood in the heart of Winston. Move-in ready with brand new floors recently installed. Minimal outdoor maintenance. Garden shed and room to park a 5th wheel. Don’t miss your opportunity to own a solid, easy-living home in a great location.

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    186 Woodduck St, Winston, OR 97496
  • /17

    $305,000

    $10K PRICE DROP Pre-Foreclosure
    • 3 Beds
    • 2 Baths
    • 1,594 Sq Ft

    340 NW Elizabeth Ave, Winston, OR 97496

    This 3-bedroom, 2-bath home offers a functional layout with plenty of potential for its next owner. A few minor repairs will help unlock its full charm, making it an excellent opportunity for buyers looking to personalize a home without taking on a major renovation. Conveniently located in Winston near everyday amenities, this property is ready for its next chapter.

    Tiffanie Frasier Keller Williams Southern Oregon-Umpqua Valley

    340 NW Elizabeth Ave, Winston, OR 97496
  • /48

    $469,900

    $19K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,764 Sq Ft

    1941 Byron Creek Rd, Winston, OR 97496

    Come home to your own private escape hidden in the trees! Beautiful parklike setting with amazing views and end of the road privacy. Property features include a huge, large covered RV storage, detached guest quarters, a storeroom & workshop. The manufactured home was custom built for the current owners with many custom touches. An expansive deck is perfect for gatherings or taking in the amazing

    Andrew Stoner Roseburg Realty

    1941 Byron Creek Rd, Winston, OR 97496
  • /48

    $699,000

    $26K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,362 Sq Ft

    1068 Rice Creek Rd, Winston, OR 97496

    Security gated 8.52-acre property! This beautiful ranch-style home features, updates, paved driveway, newer roof, interior & exterior paint, gourmet kitchen, double ovens, large walk-in pantry, lots of outdoor light, large living room with a cozy fireplace, great views, huge primary bedroom with a walk-in closet and bathroom with 2-headed shower, 4th bedroom could easily be used as an office, new

    Joan Smith The Neil Company Real Estate

    1068 Rice Creek Rd, Winston, OR 97496
  • /33

    $439,900

    • 3 Beds
    • 2 Baths
    • 1,832 Sq Ft

    128 Watusi Ct, Winston, OR 97496

    Welcome home to this spacious single level home in one of Winston's nicest neighborhoods! With great curb appeal, a sprawling tastefully landscaped yard, and no HOA, this property stands out in many ways. The open kitchen with abundant cabinetry is highlighted by beautiful Quartzite countertops, an island with eating bar, pullout shelves, a pantry, and all appliances are included. There is a gas

    Rich Raynor Heritage Real Estate

    128 Watusi Ct, Winston, OR 97496
  • /41

    $329,900

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

    76 SE Darrell Ave, Winston, OR 97496

    Welcome to this brand-new, single-level contemporary home offering 3 bedrooms and 2 bathrooms with a comfortable, open-concept floor plan. The stylish kitchen features quartz countertops and stainless steel appliances, opening to the dining and living areas for easy everyday living and entertaining. The dining room provides convenient slider access to the fenced backyard.The primary suite

    Jennifer Kramer RE/MAX Integrity

    76 SE Darrell Ave, Winston, OR 97496
  • /15

    $215,000

    $24K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    90 SE Darrell Ave, Winston, OR 97496

    This charming 2-bedroom, 2-bathroom manufactured home in Winston, Oregon offers comfortable, modern living in a convenient location close to shopping, dining and other local amenities. Nestled on its own land, this home combines privacy with easy access to town.Inside, you’ll love the open-design floor plan that creates a bright, spacious feel throughout the living room, dining area and

    Rebekah Sexauer eXp Realty, LLC

    90 SE Darrell Ave, Winston, OR 97496
  • /31

    $98,000

    • 3 Beds
    • 2 Baths
    • 1,215 Sq Ft

    190 Twin Oaks Loop, Winston, OR 97496

    Welcome to this cozy 3-bedroom, 2-bathroom home located in the sought-after Twin Oaks Mobile Park Estates. Situated in a quiet and well-maintained 55+ community in Winston, Oregon, this charming property offers the perfect blend of comfort and conveniences. This home features a spacious, functional open floor plan. The living room flows seamlessly into a modern kitchen, which comes complete with

    Kimberley Ferguson eXp Realty, LLC

    190 Twin Oaks Loop, Winston, OR 97496
  • /35

    $160,000

    • 3 Beds
    • 2 Baths
    • 1,176 Sq Ft

    105 Stephanie Ct, Winston, OR 97496

    Welcome home to this well-maintained single-level home offering comfort, convenience, and an inviting open-concept design. The spacious living area flows seamlessly into a beautifully appointed kitchen featuring abundant cabinet storage, a pantry, stainless steel appliances, and a large island perfect for meal prep, casual dining, or gathering with family and friends.Luxury vinyl plank flooring

    Tammi Ellison eXp Realty, LLC

    105 Stephanie Ct, Winston, OR 97496
  • /15

    $150,000

    $30K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 784 Sq Ft

    101 NE Darrell Ave, Winston, OR 97496

    Charming affordable singlewide manufacture home on .18 of an acre, located on a corner lot. This 2 bedroom, 1 bath home has a covered front porch and back deck with a chain link fenced yard. Storage shed and off street parking.

    Nancy Wood Oregon Life Homes

    101 NE Darrell Ave, Winston, OR 97496
  • /30

    $195,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,323 Sq Ft

    381 SE Gregory Dr, Winston, OR 97496

    Incredible and rare opportunity in Winston, Oregon! Developers, investors, and visionaries take notice. This charming 1940s 2-bedroom, 1-bath home is full of character and ready for its next chapter. With a little vision and elbow grease, this property offers endless possibilities.Situated on a spacious, level lot with mature greenery, the property presents potential for future development,

    Shae Ellison Platinum Realty

    381 SE Gregory Dr, Winston, OR 97496
  • /26

    $135,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    134 NW Anne Ave, Winston, OR 97496

    Well maintained 1296 sf manufactured home with a very functional floor plan. This home has 3 bedrooms, 2 bathrooms, a spacious living room and kitchen with plenty of storage including a walk-in pantry, separate dining room and laundry room. The home is located on a nice size lot that has fully fenced front and back yards, a large storage shed, carport, and an additional carport. This home is

    Debra Moore Currieco Real Estate

    134 NW Anne Ave, Winston, OR 97496
  • /47

    $489,900

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,928 Sq Ft

    263 Wil Way, Winston, OR 97496

    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 Gilbert Keller Williams Southern Oregon-Umpqua Valley

    263 Wil Way, Winston, OR 97496
  • /34

    $350,000

    $9K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,710 Sq Ft

    380 NW Cary St, Winston, OR 97496

    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.

    Willow Pearson Oregon Life Homes

    380 NW Cary St, Winston, OR 97496
  • /22

    $498,000

    $52K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft

    572 Dillard Gardens Rd, Winston, OR 97496

    Charming farmhouse on the South Umpqua River. Set on 6.9 acres with prime farmland, water rights and an established cherry orchard. The home features wood floors, good natural light, a cozy living room, open kitchen and dining area. Large primary bedroom with a full bathroom and walk in closet. 2nd bedroom is utilized as an office. Laundry room and detached garage. Back yard filled with flowers

    Mike Nichols MORE Realty, Inc.

    572 Dillard Gardens Rd, Winston, OR 97496
  • /22

    $299,000

    $16K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,348 Sq Ft

    101 SW Peach Ln, Winston, OR 97496

    This single-level home features 3 bedrooms and 1 bathroom, offering comfortable and convenient living. Step outside to a spacious, fully fenced backyard perfect for pets, play or entertaining. Garden enthusiasts will appreciate the dedicated garden area, while multiple tool sheds provide ample storage for tools, equipment and hobbies. A large covered real patio creates an ideal space for

    Joe Hajos Berkshire Hathaway HomeServices Real Estate Professionals

    101 SW Peach Ln, Winston, OR 97496
  • /23

    $60,000

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    124 Country Side Ln, Winston, OR 97496

    Welcome home to this charming home located in a beautifully maintained 55+ community! With 3 bedrooms, 2 baths, and 1,296 sq. ft. of inviting living space, this home features vaulted ceilings, a bright open layout, and a manicured corner lot. The walk-through kitchen includes a breakfast bar, built-in microwave, stove, refrigerator, and a brand-new dishwasher. The spacious primary suite offers

    Jason Mann J Mann Realty

    124 Country Side Ln, Winston, OR 97496
  • /48

    $487,000

    Open Sat 11AM - 2PM
    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    104 Kenya Ct, Winston, OR 97496

    This remarkable home showcases incredible attention to detail throughout, offering a spacious and unique floor plan designed for both comfort and functionality. The large kitchen features an eating bar, granite countertops, new appliances, abundant cabinet storage, overhead and can lighting, and walk-in pantry. The dining room offers beautiful built-in storage, adding both character and

    Shae Ellison Platinum Realty

    104 Kenya Ct, Winston, OR 97496
  • /43

    $99,000

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    180 Twin Oaks Loop, Winston, OR 97496

    WOW! Enjoy affordable living in the sought-after 55+ Twin Oaks community! This spacious 3-bedroom, 2-bath double-wide offers 1404 square feet of comfortable living space with a thoughtful split-bedroom floor plan and vaulted ceilings. The oversized living room flows into the dining area, where a built-in hutch adds both charm and extra storage. The kitchen features granite tile countertops,

    Anthony Beckham Different Better Real Estate

    180 Twin Oaks Loop, Winston, OR 97496
  • /17

    $335,000

    $4K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,257 Sq Ft

    185 SE Lebleu Ln, Winston, OR 97496

    Picture enjoying your morning coffee on the back deck looking out over a peach orchard! This very tidy and well-maintained 3 bedroom, 2 bath house is situated in a quiet neighborhood and borders Brosi Orchards. Step inside to the living room with vaulted ceilings and gas fireplace, perfect for relaxing after a long day. Smartly designed layout with private master suite on one end of the home.

    Sandra Hart The Neil Company Real Estate

    185 SE Lebleu Ln, Winston, OR 97496
  • /23

    $364,900

    $24K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft

    10 SW Peach Ln, Winston, OR 97496

    Welcome to 10 SW Peach Ln, where every day feels like a peaceful retreat and every corner invites you to slow down and savor the moment. This special property blends warmth, character, and an unforgettable backyard oasis designed to elevate your everyday living.Step outside and imagine hosting summer gatherings on the resort-style brick patio, unwinding beside the soothing sounds of your private

    Kimberly Krebs Stellar Realty Northwest

    10 SW Peach Ln, Winston, OR 97496
  • /48

    $1,100,000

    $100K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,720 Sq Ft

    6700 Upper Olalla Rd, Winston, OR 97496

    One of a kind custom cedar home on 5 level, usable acres—an incredible country property with space, privacy, and outstanding amenities! This Lindal style home includes a massive 2,400 sq ft shop with a full bathroom, dual garage doors, and room for a 40-foot motorhome. Three RV hookups provide power, water, and dump access—an exceptional setup for guests, RV parking, recreational vehicles, and

    Dan Gandee Real Broker

    6700 Upper Olalla Rd, Winston, OR 97496
  • /30

    $255,000

    $5K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,070 Sq Ft

    3707 Willis Creek Rd, Winston, OR 97496

    Rare rural opportunity priced at land and utility value — for the investor, builder, or country-living dreamer ready to create something truly their own in the hills of Douglas County, Oregon. Utilities are already in place — a significant head start on any rural build. The property is served by Pacific Power electric and Winston City Water (public water), with an on-site septic system. Septic

    Michelle Kohlhoff Sundance Realty LLC

    3707 Willis Creek Rd, Winston, OR 97496
  • /26

    $270,000

    $48K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    340 SE Darrell Ave, Winston, OR 97496

    ***JUST LOWEREDD PRICE BY $48,000!!!*** Solid 3-bedroom, single-level home with a functional layout, attached garage, and fully fenced yard with covered patio, and front porch.The home features a ductless heat pump for efficient heating and cooling, along with comfortable interior living spaces. Roof replaced within the last few years. Primary bedroom includes a walk-in closet and crown molding.

    Aaron Stansbury Keller Williams Realty Eugene and Springfield

    340 SE Darrell Ave, Winston, OR 97496
  • /32

    $259,000

    $21K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    509 NW Elwood Dr, Winston, OR 97496

    This adorable 3-bedroom, 1-bathroom home is the perfect starter home or an excellent addition to your investment portfolio. The kitchen was remodeled earlier this year. Conveniently located close to an elementary school, shopping, and everyday amenities, this home combines comfort with convenience. Whether you’re a first-time homebuyer, looking to downsize, or searching for a rental property,

    Jada Whited Oregon Life Homes

    509 NW Elwood Dr, Winston, OR 97496
  • /19

    $18,499

    $11K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,022 Sq Ft

    228 Estate Loop, Winston, OR 97496

    2 bed, 1 bath home in a desirable 55+ park featuring spacious living areas and a well-appointed kitchen with breakfast bar. Attached dining area includes built-ins for added storage and charm. Separate laundry room, plus a bathroom with walk-in shower for convenience. Outside features include covered porch, carport with attached storage area. Located close to shopping, dining, and other amenities.

    Jason Mann J Mann Realty

    228 Estate Loop, Winston, OR 97496
  • /4

    $2,000,000

    • 4 Beds
    • 2 Baths
    • 1,992 Sq Ft

    80 NW Lost Ln, Winston, OR 97496

    Great Property for future Developing. 2007 Manufactured Home on .68 of a Ac. City Water and Sewer.

    Dawn Trapalis Harcourts Integrity Team Real Estate Services, LLC.

    80 NW Lost Ln, Winston, OR 97496
  • /48

    $1,099,900

    $100K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,856 Sq Ft

    1349 Willis Creek Rd, Winston, OR 97496

    Quiet country living on private acreage! Offered for the first time ever, this exceptional estate presents a rare opportunity to own a truly special piece of the Pacific Northwest. Featuring two separate residences, this property is perfectly suited for multi-generational living, guest accommodations, or potential rental income. The primary home offers over 2,800 square feet of inviting living

    Jordan Anderson The Anderson Agency

    1349 Willis Creek Rd, Winston, OR 97496
  • /23

    $469,900

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

    161 Collins Rd, Winston, OR 97496

    Brand-new construction in the desirable Lookingglass Creek Estates subdivision! This functionally designed home features an open floor plan with high-end finishes throughout. Offering 3 bedrooms, 2 bathrooms, & 1770 sqft. The kitchen offers beautiful custom soft-close cabinets, quartz countertops, pantry, and waterproof luxury vinyl plank flooring. The spacious primary suite offers a walk-in

    Jacob Gilman The Neil Company Real Estate

    161 Collins Rd, Winston, OR 97496
  • /30

    $399,000

    $11K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,498 Sq Ft

    675 SE Brush Ct, Winston, OR 97496

    This beautifully maintained home is tucked away in a cul-de-sac in the heart of Winston, offering both privacy and convenience. With three comfortable bedrooms and two well-appointed bathrooms, the open-concept layout creates a welcoming atmosphere that’s ideal for hosting gatherings. The kitchen features a spacious island, perfect for preparing meals and entertaining guests. Vaulted ceilings in

    Christina Esterbrook J Mann Realty

    675 SE Brush Ct, Winston, OR 97496
  • /48

    $439,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft

    535 SE Parkway Dr, Winston, OR 97496

    Must see to believe!! Get inside this beautiful home! Enjoy your own Fourth of July fireworks show from the comfort of your rear deck with front-row views of the surrounding area! Meticulously maintained single-level home located in the highly desirable Parkway Subdivision. Offering 1,442 square feet of comfortable living space, this home features 3 bedrooms and 2 bathrooms and is situated on a

    Lisa Ollivant RE/MAX Integrity

    535 SE Parkway Dr, Winston, OR 97496
  • /28

    $309,900

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    351 SE Darrell Ave, Winston, OR 97496

    JUST REDUCED!! This 3 Bedroom/1 Bath, family home on over 1/3-acre has been completely updated for your enjoyment. There are many new items, including roof, mini split system, LVP flooring throughout, interior and exterior paint, plumbing and outside waterline. The bathroom/laundry room has been completely renovated. The yards are fully fenced, and there is a nice large deck on the back

    Debra Moore Currieco Real Estate

    351 SE Darrell Ave, Winston, OR 97496
  • /10

    $439,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,564 Sq Ft

    158 Collins Ct, Winston, OR 97496

    Nestled in the highly desired Lookingglass Creek Estates Subdivision in Winston. This brand-new home provides exceptional design and craftsmanship, with a popular floor plan that ensures comfort and style. The heart of this home, the kitchen, is adorned with quartz countertops & custom cabinets that extend to the bathrooms, adding elegance and durability. The property comes with the added

    Jacob Gilman The Neil Company Real Estate

    158 Collins Ct, Winston, OR 97496
  • /16

    $285,000

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft

    261 SE Darrell Ave, Winston, OR 97496

    Wonderful little cottage for the first time home buyer or the investor needing one more rental in there portfolio. This home is located on a double lot. Per city of Winston, lot is dividable. Build an additional house on its own lot, or leave it as-is and build an ADU or shop in your backyard. Come check this out and make your appointment today.

    Angel Smith Trueblood Real Estate

    261 SE Darrell Ave, Winston, OR 97496

Home Price Trends

Median Sale Price
$325,000
Median Single Family Sale Price
$354,200
Median 2 Bedroom Sale Price
$221,500
Median 1 Bedroom Sale Price
$148,000
Average Price Per Sq Ft
$232
Number of Homes for Sale
28
Last 12 months Home Sales
67
Months of Supply
5.00
Median List Price
$373,500
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-4%
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