9

Winston, OR 2-Story Homes for Sale

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  • 635 Wil Way, Winston, OR 97496
    635 Wil Way, Winston, OR 97496
    635 Wil Way, Winston, OR 97496
    /45

    $715,000

    • 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
  • 800 Byron Creek Rd, Winston, OR 97496
    800 Byron Creek Rd, Winston, OR 97496
    800 Byron Creek Rd, Winston, OR 97496
    /35

    $495,000

    • 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
  • 617 Poison Oak Dr, Winston, OR 97496
    617 Poison Oak Dr, Winston, OR 97496
    617 Poison Oak Dr, Winston, OR 97496
    /39

    $300,000

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

    617 Poison Oak Dr, Winston, OR 97496

    Escape to the country with this rustic home nestled on nearly 14 beautiful acres. Perfect for those dreaming of a mini-farm or simply wanting space for animals, and rural lifestyle. This property offers usable acreage mixed with stands of timber, seasonal creeks and endless potential. Surround yourself with sweeping mountain views and the serenity of nature, all while enjoying the freedom that

    Bob Lamonte Lamonte Real Estate Professionals

    617 Poison Oak Dr, Winston, OR 97496
  • 13224 Lookingglass Rd, Winston, OR 97496
    13224 Lookingglass Rd, Winston, OR 97496
    13224 Lookingglass Rd, Winston, OR 97496
    /46

    $479,900

    • 4 Beds
    • 2 Baths
    • 2,534 Sq Ft

    13224 Lookingglass Rd, Winston, OR 97496

    Experience the unique allure of this beautifully updated, original homestead farmhouse nestled in Safari Estates. Thoughtful remodel and tasteful updates have modernized this 1900-built farmhouse, preserving its character while enhancing comfort. With 2,516 sq ft of living space, four bedrooms, and two full baths, this home blends historic charm with modern comfort. The kitchen has been remodeled

    Deleta Dickson eXp Realty, LLC

    13224 Lookingglass Rd, Winston, OR 97496
  • 0 Rice Creek Rd, Winston, OR 97496
    0 Rice Creek Rd, Winston, OR 97496
    0 Rice Creek 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
  • 1090 E Willis Creek Rd, Winston, OR 97496
    1090 E Willis Creek Rd, Winston, OR 97496
    1090 E Willis Creek Rd, Winston, OR 97496
    /25

    $695,000

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

    1090 E Willis Creek Rd, Winston, OR 97496

    Secluded private 2167 sq ft 3 br 2 bath contemporary home on 9.81 acres. Has open beam ceilings, wood stove, barn, wood shop, 2 gar garage. Garden area, city water, creek. Mostly level property. Charming kitchen with large pantry and skylight, ample dining room overlooking the garden and yard. Living room has bay window and room to entertain. Covered parking for boat or RV.

    Valynn Currie Currieco Real Estate

    1090 E Willis Creek Rd, Winston, OR 97496
  • 375 Porter Creek Rd, Winston, OR 97496
    375 Porter Creek Rd, Winston, OR 97496
    375 Porter Creek Rd, Winston, OR 97496
    /41

    $830,000

    • 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
  • 102 Sarah Bear Ln, Winston, OR 97496
    102 Sarah Bear Ln, Winston, OR 97496
    102 Sarah Bear Ln, Winston, OR 97496
    /32

    $585,000

    • 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
  • 1470 E Willis Creek Rd, Winston, OR 97496
    1470 E Willis Creek Rd, Winston, OR 97496
    1470 E Willis Creek Rd, Winston, OR 97496
    /48

    $749,000

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

    1470 E Willis Creek Rd, Winston, OR 97496

    Build a second home? 3 tax lots. 80+5+5 acres each & one of the 5-acre lots is buildable! Connected to city water with a 2500 reserve tank. 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,

    Rhonda Marshall Knipe Realty ERA Powered

    1470 E Willis Creek Rd, Winston, OR 97496
Oregon Douglas County Winston

2-Story Homes for Sale in Winston, OR

Home Trends in Winston, OR

On average, homes in Winston, OR sell after 67 days on the market compared to the national average of 52 days. The median sale price for homes in Winston, OR over the last 12 months is $338,000, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$338,000
Median Single Family Sale Price
$339,500
Average Price Per Sq Ft
$234
Number of Homes for Sale
21
Last 12 months Home Sales
63
Months of Supply
4.00
Median List Price
$357,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
-3%
How to Buy a Home How to Finance a Home How to Sell a Home

In Winston, there are currently 9 two-story homes for sale, offering abundant choices for those who prioritize both convenience and functionality in their living space. Whether you're in the market for a traditional two-story house or considering the versatility of a two-story townhome, these properties provide a wealth of options to explore. Ranging from compact yet cozy condos to expansive family residences, the two-story homes for sale in Winston, OR come in various sizes and floorplans, ensuring there's something to accommodate every lifestyle and preference.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

The content relating to real estate for sale on this web site comes in part from the IDX program of the RMLS™ of Portland, Oregon. Real estate listings held by brokerage firms other than Ten-X are marked with the RMLS™ logo, and detailed information about these properties includes the names of the listing brokers. Listing content is copyright © 2025 RMLS™, Portland, Oregon. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available. All information provided is deemed reliable but is not guaranteed and should be independently verified.

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