3,178

Winston, OR Homes

Section Image
    • /47

      Not Listed For Sale

      258 NW Bree Dr, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft
      • Built 1998
      258 NW Bree Dr, Winston, OR 97496

      Last Sold Summary

      • $68/SF
      • 64 Days On Market

      Last Sold Price $107,000

      Last Listing Agent Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  • /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
  • /22

    $165,000 Sold May 01, 2025

    326 Rice Creek Rd, Winston, OR 97496

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft
    • Built 1970

    Last Sold Summary

    • 34% Below List Price
    • $246/SF
    • 393 Days On Market

    Current Estimated Value $266,863

    Last Listing Agent Ashton Faas Different Better Real Estate

    326 Rice Creek Rd, Winston, OR 97496
    • /21

      Est $217,255 Not Listed For Sale

      387 4th St, Winston, OR 97496

      • 2 Beds
      • 1 Bath
      • 748 Sq Ft
      • Built 1940
      387 4th St, Winston, OR 97496

      Last Sold Summary

      • 3% Below List Price
      • $301/SF
      • 34 Days On Market

      Last Sold Price $225,000

      Last Listing Agent Jane Volkova Hearthstone Real Estate

  • /32

    $555,000 Open House 4/12

    • 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
  • /41

    $285,000 Sold Jun 09, 2025

    73 NE Ronald St, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1997

    Last Sold Summary

    • 5% Below List Price
    • $165/SF
    • 137 Days On Market

    Current Estimated Value $295,866

    Last Listing Agent Dawn Trapalis Harcourts Integrity Team Real Estate Services, LLC.

    73 NE Ronald St, Winston, OR 97496
    • /29

      Est $371,916 Not Listed For Sale

      177 NW Woodduck St, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,613 Sq Ft
      • Built 2005
      177 NW Woodduck St, Winston, OR 97496

      Last Sold Summary

      • 5% Above List Price
      • $220/SF
      • 1 Day On Market

      Last Sold Price $355,000

      Last Listing Agent D'Anna Caylor RE/MAX

  • /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
  • /48

    $425,000 Sold Sep 12, 2025

    7941 Upper Olalla Rd, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 2,167 Sq Ft
    • Built 2007

    Last Sold Summary

    • 32% Below List Price
    • $196/SF
    • 139 Days On Market

    Last Listing Agent Carol Williams The Neil Company Real Estate

    7941 Upper Olalla Rd, Winston, OR 97496
    • /41

      Est $426,079 Not Listed For Sale

      430 Serengeti Dr, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,730 Sq Ft
      • Built 2016
      430 Serengeti Dr, Winston, OR 97496

      Last Sold Summary

      • 1% Below List Price
      • $248/SF
      • 2 Days On Market

      Last Sold Price $429,000

      Last Listing Agent Linda Jacobson Harcourts Integrity Team Real Estate Services, LLC.

  • /30

    $399,999

    • 2 Beds
    • 1.5 Baths
    • 1,040 Sq Ft

    270 Sabrina Ln, Winston, OR 97496

    Tucked away in the peaceful countryside of Douglas County, this unique 8-acre property offers the perfect blend of self-sufficiency, privacy, and convenience—just a 15-minute drive from Winston, Oregon. The two-story home features approximately 1,050 square feet of comfortable living space, surrounded by nature and open skies that create a true sense of seclusion.The land is thoughtfully equipped

    Robinson Parker Oregon Life Homes

    270 Sabrina Ln, Winston, OR 97496
  • /28

    $376,000 Sold Nov 19, 2025

    140 Teresa Ln, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,592 Sq Ft
    • Built 2017

    Last Sold Summary

    • 6% Below List Price
    • $236/SF
    • 164 Days On Market

    Current Estimated Value $376,542

    Last Listing Agent Jason Mann J Mann Realty

    140 Teresa Ln, Winston, OR 97496
    • /21

      Est $376,003 Not Listed For Sale

      211 NW Plum Ln, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,704 Sq Ft
      • Built 2000
      211 NW Plum Ln, Winston, OR 97496

      Last Sold Summary

      • 4% Above List Price
      • $211/SF
      • 129 Days On Market

      Last Sold Price $360,000

      Last Listing Agent Timothy A Smith RE/MAX

  • /40

    $499,900 New Construction

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

    150 Wil Way, Winston, OR 97496

    OPEN HOUSE! Sunday 1-3pm 3/29 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
  • /43

    $825,000 Sold May 22, 2025

    1800 E Willis Creek Rd, Winston, OR 97496

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft
    • Built 1991

    Last Sold Summary

    • 8% Below List Price
    • $764/SF
    • 231 Days On Market

    Current Estimated Value $695,436

    Last Listing Agent Rhonda Marshall KNIPE REALTY ERA POWERED

    1800 E Willis Creek Rd, Winston, OR 97496
    • /32

      Est $370,081 Not Listed For Sale

      400 Galaxy Dr, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,410 Sq Ft
      • Built 2024
      400 Galaxy Dr, Winston, OR 97496

      Last Sold Summary

      • $264/SF
      • 37 Days On Market

      Last Sold Price $371,900

      Last Listing Agent Shane Mast Oregon Life Homes

  • /29

    $412,500

    • 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
  • /15

    $180,000 Sold Apr 22, 2025

    315 Degnath Gateway Ln, Winston, OR 97496

    • 2 Beds
    • 2 Baths
    • 972 Sq Ft
    • Built 1982

    Last Sold Summary

    • 18% Below List Price
    • $185/SF
    • 142 Days On Market

    Current Estimated Value $193,958

    Last Listing Agent Amy Dean Amy Dean Real Estate, Inc.

    315 Degnath Gateway Ln, Winston, OR 97496
    • /5

      Est $72,000 Not Listed For Sale

      0 Hidden Hill Ln Unit 500, Winston, OR 97496

      0 Hidden Hill Ln Unit 500, Winston, OR 97496

      Last Sold Summary

      • 3% Below List Price
      • 28 Days On Market

      Last Sold Price $74,000

      Last Listing Agent Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  • /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
  • /46

    $386,500 Sold Feb 17, 2026

    890 SE Thompson Ave, Winston, OR 97496

    • 3 Beds
    • 2.5 Baths
    • 1,768 Sq Ft
    • Built 2016

    Last Sold Summary

    • 1% Below List Price
    • $219/SF
    • 73 Days On Market

    Current Estimated Value $385,363

    Last Listing Agent Anthony Beckham Different Better Real Estate

    890 SE Thompson Ave, Winston, OR 97496
    • /27

      Est $446,462 Not Listed For Sale

      124 Citation Ct, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,770 Sq Ft
      • Built 2024
      124 Citation Ct, Winston, OR 97496

      Last Sold Summary

      • 1% Below List Price
      • $254/SF
      • 46 Days On Market

      Last Sold Price $449,900

      Last Listing Agent Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  • /21

    $250,000

    • Land
    • 27.31 Acres
    • $9,154 per Acre

    0 E Willis Creek Rd, Winston, OR 97496

    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

    Art Dillahay Oregon Life Homes

    0 E Willis Creek Rd, Winston, OR 97496
  • /46

    $415,000 Sold Oct 15, 2025

    128 Watusi Ct, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,832 Sq Ft
    • Built 2008

    Last Sold Summary

    • 2% Below List Price
    • $227/SF
    • 20 Days On Market

    Current Estimated Value $420,463

    Last Listing Agent Thomas Gulan RE/MAX Integrity

    128 Watusi Ct, Winston, OR 97496
    • /16

      Est $306,251 Not Listed For Sale

      1420 Winston Section Rd, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,292 Sq Ft
      • Built 2024
      1420 Winston Section Rd, Winston, OR 97496

      Last Sold Summary

      • 3% Above List Price
      • $230/SF
      • 3 Days On Market

      Last Sold Price $297,000

      Last Listing Agent Sabrina Jorgensen Fathom Realty Oregon, LLC

  • /21

    $150,000

    • Land
    • 10.56 Acres
    • $14,205 per Acre

    3541 Willis Creek Rd, Winston, OR 97496

    10.56 Acres Bordering Public Land Nestled at 3541 Willis Creek Rd, this 10.56-acre property offers a rare chance to own a slice of Oregon's natural beauty. With a newly cut-in road leading to a potential home site, you'll enjoy a stunning view of the valley-a perfect backdrop for your future home. The essentials are already in place: Community water with a meter installed near the south end

    Cliff Farley Mossy Oak Properties Oregon Field and Stream Realty

    3541 Willis Creek Rd, Winston, OR 97496
  • /29

    $279,400 Sold Aug 27, 2025

    520 SE Dawna Ct, Winston, OR 97496

    • 3 Beds
    • 1 Bath
    • 1,005 Sq Ft
    • Built 1989

    Last Sold Summary

    • 7% Below List Price
    • $278/SF
    • 143 Days On Market

    Current Estimated Value $275,149

    Last Listing Agent Ashley Oberman Oregon Life Homes

    520 SE Dawna Ct, Winston, OR 97496
    • /40

      Est $425,172 Not Listed For Sale

      285 SE Logan St, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,792 Sq Ft
      • Built 2008
      285 SE Logan St, Winston, OR 97496

      Last Sold Summary

      • $237/SF
      • 2 Days On Market

      Last Sold Price $424,000

      Last Listing Agent Darryl Bodle Keller Williams Realty Portland Premiere

  • /39

    $225,000 Pending

    • 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
  • /47

    $358,400 Sold Jul 11, 2025

    149 Teresa Ln, Winston, OR 97496

    • 3 Beds
    • 2.5 Baths
    • 1,250 Sq Ft
    • Built 2020

    Last Sold Summary

    • $287/SF
    • 224 Days On Market

    Current Estimated Value $352,499

    Last Listing Agent Jennifer Kramer RE/MAX Integrity

    149 Teresa Ln, Winston, OR 97496
    • /13

      Not Listed For Sale

      212 NW Bree Dr, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,428 Sq Ft
      • Built 1999
      212 NW Bree Dr, Winston, OR 97496

      Last Sold Summary

      • $46/SF
      • 102 Days On Market

      Last Sold Price $66,000

      Last Listing Agent Amber Rau eXp Realty, LLC

  • /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
  • /48

    $240,000 Sold Jun 05, 2025

    66 NW Cary St, Winston, OR 97496

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft
    • Built 1955

    Last Sold Summary

    • 4% Above List Price
    • $288/SF
    • 4 Days On Market

    Current Estimated Value $235,922

    Last Listing Agent Elena Mackey eXp Realty, LLC

    66 NW Cary St, Winston, OR 97496
    • /38

      Est $418,440 Not Listed For Sale

      50 SW Civil Bend Ave, Winston, OR 97496

      • 3 Beds
      • 3 Baths
      • 2,412 Sq Ft
      • Built 1969
      50 SW Civil Bend Ave, Winston, OR 97496

      Last Sold Summary

      • 5% Above List Price
      • $166/SF
      • 15 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Patti Archambault All-Pro Realty Advisors, LLC

  • /36

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,416 Sq Ft

    669 NW T St, Winston, OR 97496

    Welcome to this beautiful 2022 built home in Winston, Oregon, offering comfort, privacy, and stunning open views. Conveniently located close to local amenities with easy access to the Oregon Coast and the world-famous Wildlife Safari. Situated on a private and spacious flag lot, the property backs to a school field, creating an open feel with peaceful mountain views and added privacy.Inside,

    Shae Ellison Platinum Realty

    669 NW T St, Winston, OR 97496
  • /35

    $169,900 Sold Jan 20, 2026

    222 NW Broc Dr, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • Built 2024

    Last Sold Summary

    • $112/SF
    • 26 Days On Market

    Last Listing Agent Anthony Beckham Different Better Real Estate

    222 NW Broc Dr, Winston, OR 97496
    • /23

      Est $223,226 Not Listed For Sale

      1047 Oregon 42, Winston, OR 97496

      • 2 Beds
      • 1.5 Baths
      • 1,746 Sq Ft
      • Built 1959
      1047 Oregon 42, Winston, OR 97496

      Last Sold Summary

      • 54% Above List Price
      • $83/SF
      • 61 Days On Market

      Last Sold Price $144,900

      Last Listing Agent Rick Richtik The Neil Company Real Estate

  • /20

    $230,000

    • 2 Beds
    • 1 Bath
    • 1,323 Sq Ft

    381 SE Gregory Dr, Winston, OR 97496

    Seize this opportunity with this charming single-story 1948 ranch style home boasting 2 bedrooms, 1 bath, and about 1,323 sq ft of living space on a generous 0.61-acre lot. Surrounded by mature trees and offering a peaceful, rural-suburban feel in the heart of Douglas County. This mid-century gem features timeless details like a prominent brick chimney, large picture windows for natural light,

    Nile Stark RE/MAX Integrity

    381 SE Gregory Dr, Winston, OR 97496
  • /35

    $399,900 Sold Feb 20, 2026

    364 NW Teal St, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,684 Sq Ft
    • Built 2007

    Last Sold Summary

    • 7% Below List Price
    • $237/SF
    • 112 Days On Market

    Current Estimated Value $401,426

    Last Listing Agent Joe Hajos Berkshire Hathaway HomeServices Real Estate Professionals

    364 NW Teal St, Winston, OR 97496
    • /3

      Not Listed For Sale

      0 NW Civil Bend Ave Unit 24521552, Winston, OR 97496

      0 NW Civil Bend Ave Unit 24521552, Winston, OR 97496

      Last Sold Summary

      • 1 Day On Market

      Last Sold Price $85,000

      Last Listing Agent Emily Volk Karen Volk Realty

Showing Results 41 - 80, Page 2 of 18

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