25

Winston, OR Homes for Sale with Garage

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  • /27

    $357,900

    • 3 Beds
    • 2 Baths
    • 1,433 Sq Ft

    380 SE Sunnyside Dr, Winston, OR 97496

    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

    Agent Photo

    Rockwell Group

    eXp Realty, LLC

    (458) 224-8911

    380 SE Sunnyside Dr, Winston, OR 97496
  • /45

    $679,900

    • 4 Beds
    • 3.5 Baths
    • 3,072 Sq Ft

    635 Wil Way, Winston, OR 97496

    One of a kind property that is a true gem. Panoramic views of the Abacela Vineyards, the Wildlife Safari, the beautiful city, and the stunning valleys. While being tucked away at the end of the road for extra privacy. Nestled on over 20 acres, this parcel adjoins the Wildlife Safari. Imagine watching exotic animals from your back yard! The home is a gorgeous 2019 build featuing many high quality

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 232-3589

    635 Wil Way, Winston, OR 97496
  • /47

    $499,900

    • 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
  • /45

    $66,000 Open Sat 3PM - 5PM

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    125 SE Estate Loop, Winston, OR 97496

    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 Gilbert Keller Williams Southern Oregon-Umpqua Valley

    125 SE Estate Loop, Winston, OR 97496
  • /36

    $409,000

    • 7 Beds
    • 4.5 Baths
    • 3,861 Sq Ft

    2414 Brockway Rd, Winston, OR 97496

    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 Gilbert Keller Williams Southern Oregon-Umpqua Valley

    2414 Brockway Rd, Winston, OR 97496
  • /48

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft

    210 NW Timothy Ave, Winston, OR 97496

    Welcome to this beautifully maintained triple-wide manufactured home offering 1,848 sq ft of spacious, comfortable living on a desirable corner lot. Situated on a .25-acre parcel, this 3-bedroom, 2-bath home combines functionality, style, and outdoor enjoyment. Step inside to an inviting layout featuring vaulted ceilings and abundant natural light throughout. The large kitchen is a true

    Jennifer Kramer RE/MAX Integrity

    210 NW Timothy Ave, Winston, OR 97496
  • /34

    $359,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 2 Baths
    • 1,710 Sq Ft

    380 NW Cary St, Winston, OR 97496

    Open house April 11th from 12 - 2pm.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
  • /39

    $160,000

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

    157 NW Bree Dr, Winston, OR 97496

    Pride of ownership shows in this 3 bedroom, 2 bath manufactured home in an all-ages park with low space rent. This one is truly move-in ready with a lot of the big stuff already done—newer roof, water heater, appliances, and even a shed for extra storage. The layout just makes sense with good living space, tons of natural light, and a separate office that works great for working from home or

    Anthony Beckham Different Better Real Estate

    157 NW Bree Dr, Winston, OR 97496
  • /48

    $1,200,000

    • 3 Beds
    • 2.5 Baths
    • 2,720 Sq Ft

    6700 Upper Olalla Rd, Winston, OR 97496

    Exquisite Lindal Custom Cedar home on 5 flat acres featuring a 2,400 sq ft shop with full bath, dual doors, and room for a 40’ motorhome, plus 3 RV hookups (2 across the driveway) with power, water, and RV dump by the shop. The gourmet kitchen is a chef’s dream with granite counters, dual sinks, pot filler, gas range with warming drawer, double ovens, hidden butcher block, and abundant storage,

    Dan Gandee Real Broker

    6700 Upper Olalla Rd, Winston, OR 97496
  • /11

    $199,900

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft

    1580 Winston Section Rd, Winston, OR 97496

    This 3-bedroom, 2-bathroom "fixer upper" sits on a peaceful 0.18-acre corner lot, offering a quiet atmosphere and beautiful mountain views right from your doorstep. While the home is ready for interior renovation, the floor plan features three bedrooms, two bathrooms, laundry room, large kitchen, creating a cozy feeling once restored. A standout is the 576 sqft detached garage/shop, where half

    Cynthia Beach The Neil Company Real Estate

    1580 Winston Section Rd, Winston, OR 97496
  • /27

    $357,900

    • 3 Beds
    • 2 Baths
    • 1,433 Sq Ft

    380 Sunnyside Dr, Winston, OR 97496

    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

    Chase Lee eXp Realty, LLC

    380 Sunnyside Dr, Winston, OR 97496
  • /21

    $195,000

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft

    751 SE Meadowood Dr, Winston, OR 97496

    1995 Double-wide manufactured home on a good sized lot in Winston. Not perfect but a lot of home for the money. Central heat and air conditioning, carport and lots of room for a garden. A great home for the money. Affordable living, close to park and community center. Roof has just been replaced.

    Timothy A Smith RE/MAX Integrity

    751 SE Meadowood Dr, Winston, OR 97496
  • /29

    $399,900

    • 3 Beds
    • 2.5 Baths
    • 1,874 Sq Ft

    241 SE Johnson St, Winston, OR 97496

    Almost-new two-story home offering 3 bedrooms, 2.1 baths, and 1,874 sq. ft. of comfortable living space, gently occupied for just two years. Enjoy both front and back porches—ideal for relaxing or entertaining. The kitchen features soft-close cabinets and a gas range, while the extra-large laundry/utility room adds everyday convenience. Additional features include ductless heating and A/C, a gas

    Mandy Parker Oregon Life Homes

    241 SE Johnson St, Winston, OR 97496
  • /42

    $599,000

    • 3 Beds
    • 2 Baths
    • 2,431 Sq Ft

    605 Deerwood Ct, Winston, OR 97496

    This custom-built Passive Solar home, constructed in 1979, offers a rare blend of timeless beauty, retro charm, and thoughtful modern updates. This Passive Solar home is thoughtfully designed to work with the sun and climate, providing comfort, efficiency, and sustainability without relying heavily on mechanical systems. Ideally located near local river recreation and just a short drive to the

    Lisa Ollivant RE/MAX Integrity

    605 Deerwood Ct, Winston, OR 97496
  • /40

    $675,000

    • 2 Beds
    • 2.5 Baths
    • 2,304 Sq Ft

    9740 Upper Olalla Rd, Winston, OR 97496

    Country setting 29.80 acres, Chalet-style home, 2304 sqft , 2 BR ( could be 3 BR) 2.5 BA. LR has a fireplace with woodstove insert and massive natural stone chimney. Good size kitchen, laundry room with extra sink. Merchantable timber, access to Seneca timber and BLM land for horseback riding, mushroom hunting, ATV's and hiking. Beautiful mountain views, year-round Olalla Creek with water right

    Thuy Chrestenson KNIPE REALTY ERA POWERED

    9740 Upper Olalla Rd, Winston, OR 97496
  • /15

    $229,000

    • 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
  • /35

    $475,000

    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    800 Byron Creek Rd, Winston, OR 97496

    Welcome to this charming country home set on over 5 acres of flat, usable land with Firewise Certification for peace of mind. The well maintained 3 bedroom with 1.5 bathrooms. Home is move-in ready, some of the furniture can be included with the right offer. House has a heat pump, pellet stove, generator, flooring- all done in last 4 years. The propane 22k generator automatically powers the home

    Rebekah Sexauer eXp Realty, LLC

    800 Byron Creek Rd, Winston, OR 97496
  • /20

    $475,000

    • 3 Beds
    • 1.5 Baths
    • 2,026 Sq Ft

    308 Helweg Rd, Winston, OR 97496

    Prime 12.91-acre agricultural property zoned (FC) Exclusive Farm Use-Cropland with 10 acres of primary pond and supplemental river irrigation rights (priority date 1983). This land is perfectly positioned for a profitable homestead, organic farm, or u-pick business. Previously used for hay production and livestock, the soil and water offer a solid foundation for success. The existing home and

    Aaron Cherry Oregon Life Homes

    308 Helweg Rd, Winston, OR 97496
  • /48

    $454,000

    • 2 Beds
    • 1 Bath
    • 2,056 Sq Ft

    0 Rice Creek Rd, Winston, OR 97496

    100% off-grid living on your own 20-acre slice of paradise! Located within "The Ranch" - a close-knit homesteading community of like-minded landowners who each steward their own property while embracing a shared off-grid lifestyle. Just 25 minutes southwest of Winston, Oregon, this property is accessed via a gated 4-mile gravel road through BLM and private timberlands. The resilient home features

    Aaron Cherry Oregon Life Homes

    0 Rice Creek Rd, Winston, OR 97496
  • /47

    $342,500

    • 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
  • /32

    $555,000 Open Sun 1PM - 3PM

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

    102 Sarah Bear Ln, Winston, OR 97496

    Meticulous quality 4 br 3 bath 2660 sq ft home, with 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

    Valynn Currie Currieco Real Estate

    102 Sarah Bear Ln, Winston, OR 97496
  • /48

    $469,900

    • 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
  • /41

    $499,900 Open Sun 1PM - 4PM

    • 3 Beds
    • 2.5 Baths
    • 2,089 Sq Ft

    160 Wil Way, Winston, OR 97496

    OPEN HOUSE! Sunday 4/12 1-4pm 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

    Tyler Head Turning Point Realty Group

    160 Wil Way, Winston, OR 97496
  • /40

    $499,900 Open Sun 1PM - 4PM

    • 3 Beds
    • 2.5 Baths
    • 1,999 Sq Ft

    150 Wil Way, Winston, OR 97496

    OPEN HOUSE! Sunday 1-4 pm 4/12 New Home by JW Construction Inc.This beautifully crafted 2,143 sq ft home offers 3 bedrooms and 2 1/2 bathrooms with a thoughtful layout and excellent separation of space. Set on a low-maintenance lot with views of trees and the surrounding mountains, 140 Wil Way combines modern design with comfort and convenience.The open-concept main level features high ceilings,

    Tyler Head Turning Point Realty Group

    150 Wil Way, Winston, OR 97496
  • /44

    $699,500

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

    411 Woodland Dr, Roseburg, OR 97471

    Discover a lifestyle rooted in fresh air, room to roam, and time spent outside. This two-story ranch sits above sweeping views of Abacela Vineyard and offers Lookingglass Creek frontage with irrigation rights, K-line system, and pump already in place. Enjoy your own private swimming hole, raised-bed fenced garden, and greenhouse—perfect for growing, tinkering, and staying active year-round.The

    Nataly Mattox RE/MAX Integrity

    411 Woodland Dr, Roseburg, OR 97471

Home Trends in Winston, OR

Housing Trends

Median Sale Price
$325,000
Median Single Family Sale Price
$342,500
Average Price Per Sq Ft
$227
Number of Homes for Sale
14
Last 12 months Home Sales
65
Months of Supply
2.60
Median List Price
$359,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-6%
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