3,191

Winston, OR Homes

Section Image
  • 2409 Ireland Rd, Winston, OR 97496
    2409 Ireland Rd, Winston, OR 97496
    2409 Ireland Rd, Winston, OR 97496
    /39

    $249,900

    Sold Jun 11, 2026

    2409 Ireland Rd, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1979

    Last Sold Summary

    • $174/SF
    • 13 Days On Market

    Last Listing Agent Jenny Forbes Pacific Properties

    2409 Ireland Rd, Winston, OR 97496
    • 530 SE Dawna Ct, Winston, OR 97496
      530 SE Dawna Ct, Winston, OR 97496
      530 SE Dawna Ct, Winston, OR 97496
      /32

      Est $313,867

      Not Listed For Sale

      530 SE Dawna Ct, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,166 Sq Ft
      • Built 1989
      530 SE Dawna Ct, Winston, OR 97496

      Last Sold Summary

      • 10 Days On Market

  • 314 NW Civil Bend Ave, Winston, OR 97496
    314 NW Civil Bend Ave, Winston, OR 97496
    314 NW Civil Bend Ave, Winston, OR 97496
    /22

    $255,000

    Sold Jun 27, 2025

    314 NW Civil Bend Ave, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 2000

    Last Sold Summary

    • 11% Above List Price
    • $197/SF
    • 4 Days On Market

    Current Estimated Value $261,697

    Last Listing Agent Karina DiStefano Lamonte Real Estate Professionals

    314 NW Civil Bend Ave, Winston, OR 97496
    • 562 SE Gregory Dr, Winston, OR 97496
      562 SE Gregory Dr, Winston, OR 97496
      562 SE Gregory Dr, Winston, OR 97496
      /26

      Est $207,356

      Not Listed For Sale

      562 SE Gregory Dr, Winston, OR 97496

      • 2 Beds
      • 1 Bath
      • 858 Sq Ft
      • Built 1955
      562 SE Gregory Dr, Winston, OR 97496

      Last Sold Summary

      • 48 Days On Market

  • 111 Sharway Ln, Winston, OR 97496
    111 Sharway Ln, Winston, OR 97496
    111 Sharway Ln, Winston, OR 97496
    /31

    $52,000

    Sold Sep 30, 2025

    111 Sharway Ln, Winston, OR 97496

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft
    • Built 1978

    Last Sold Summary

    • 12% Below List Price
    • $62/SF
    • 112 Days On Market

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

    111 Sharway Ln, Winston, OR 97496
    • 21 SE Edwards Ave, Winston, OR 97496
      21 SE Edwards Ave, Winston, OR 97496
      21 SE Edwards Ave, Winston, OR 97496
      /22

      Est $354,007

      Not Listed For Sale

      21 SE Edwards Ave, Winston, OR 97496

      • 2 Beds
      • 1,176 Sq Ft
      • Built 1951
      21 SE Edwards Ave, Winston, OR 97496

      Last Sold Summary

      • 87 Days On Market

  • 110 Anne Ave, Winston, OR 97496
    110 Anne Ave, Winston, OR 97496
    110 Anne Ave, Winston, OR 97496
    /22

    $159,900

    Sold Aug 15, 2025

    110 Anne Ave, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • Built 2018

    Last Sold Summary

    • 11% Below List Price
    • $106/SF
    • 48 Days On Market

    Last Listing Agent Kristin Fregoso RE/MAX Integrity

    110 Anne Ave, Winston, OR 97496
    • 81 SE Edwards Ave, Winston, OR 97496
      81 SE Edwards Ave, Winston, OR 97496
      81 SE Edwards Ave, Winston, OR 97496
      /38

      Est $295,858

      Not Listed For Sale

      81 SE Edwards Ave, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 2018
      81 SE Edwards Ave, Winston, OR 97496

      Last Sold Summary

      • 18 Days On Market

  • 465 SE Gregory Dr, Winston, OR 97496
    465 SE Gregory Dr, Winston, OR 97496
    465 SE Gregory Dr, Winston, OR 97496
    /47

    $325,000

    Sold Nov 03, 2025

    465 SE Gregory Dr, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Built 2021

    Last Sold Summary

    • $201/SF
    • 21 Days On Market

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

    465 SE Gregory Dr, Winston, OR 97496
    • 261 SE Grape Ave, Winston, OR 97496
      261 SE Grape Ave, Winston, OR 97496
      261 SE Grape Ave, Winston, OR 97496
      /28

      Est $216,240

      Not Listed For Sale

      261 SE Grape Ave, Winston, OR 97496

      • 2 Beds
      • 1 Bath
      • 802 Sq Ft
      • Built 1958
      261 SE Grape Ave, Winston, OR 97496

      Last Sold Summary

      • 42 Days On Market

  • 157 NW Bree Dr, Winston, OR 97496
    157 NW Bree Dr, Winston, OR 97496
    157 NW Bree Dr, Winston, OR 97496
    /39

    $152,500

    Sold May 29, 2026

    157 NW Bree Dr, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1999

    Last Sold Summary

    • 5% Below List Price
    • $118/SF
    • 31 Days On Market

    Last Listing Agent Anthony Beckham Different Better Real Estate

    157 NW Bree Dr, Winston, OR 97496
    • 261 SW Ford Ave, Winston, OR 97496
      261 SW Ford Ave, Winston, OR 97496
      261 SW Ford Ave, Winston, OR 97496
      /33

      Est $315,724

      Not Listed For Sale

      261 SW Ford Ave, Winston, OR 97496

      • 4 Beds
      • 1.5 Baths
      • 1,628 Sq Ft
      • Built 1953
      261 SW Ford Ave, Winston, OR 97496

      Last Sold Summary

      • 9 Days On Market

  • 600 SE Carrol St, Winston, OR 97496
    600 SE Carrol St, Winston, OR 97496
    600 SE Carrol St, Winston, OR 97496
    /17

    $321,000

    Sold Mar 31, 2026

    600 SE Carrol St, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,692 Sq Ft
    • Built 2000

    Last Sold Summary

    • 6% Above List Price
    • $190/SF
    • 62 Days On Market

    Current Estimated Value $321,429

    Last Listing Agent Judith Zuver Winston Realty & Insurance

    600 SE Carrol St, Winston, OR 97496
    • 91 SW Tower St, Winston, OR 97496
      91 SW Tower St, Winston, OR 97496
      91 SW Tower St, Winston, OR 97496
      /45

      Est $295,443

      Not Listed For Sale

      91 SW Tower St, Winston, OR 97496

      • 3 Beds
      • 1 Bath
      • 1,920 Sq Ft
      • Built 1953
      91 SW Tower St, Winston, OR 97496

      Last Sold Summary

      • 33 Days On Market

  • 441 NW Galaxy Dr, Winston, OR 97496
    441 NW Galaxy Dr, Winston, OR 97496
    441 NW Galaxy Dr, Winston, OR 97496
    /39

    $410,000

    Sold Nov 14, 2025

    441 NW Galaxy Dr, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,310 Sq Ft
    • Built 2002

    Last Sold Summary

    • 14% Below List Price
    • $313/SF
    • 83 Days On Market

    Current Estimated Value $410,066

    Last Listing Agent Nichole Sharman Works Real Estate

    441 NW Galaxy Dr, Winston, OR 97496
    • 280 NW Division St, Winston, OR 97496
      280 NW Division St, Winston, OR 97496
      280 NW Division St, Winston, OR 97496
      /45

      Est $292,481

      Not Listed For Sale

      280 NW Division St, Winston, OR 97496

      • 3 Beds
      • 1.5 Baths
      • 1,247 Sq Ft
      • Built 1955
      280 NW Division St, Winston, OR 97496

      Last Sold Summary

      • 9 Days On Market

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

    $85,000

    Sold Feb 06, 2026

    241 Twin Oaks Loop, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1998

    Last Sold Summary

    • 11% Below List Price
    • $66/SF
    • 97 Days On Market

    Last Listing Agent Roger Snyder Berkshire Hathaway HomeServices Real Estate Professionals

    241 Twin Oaks Loop, Winston, OR 97496
    • 520 NW Tumlin Ave, Winston, OR 97496
      520 NW Tumlin Ave, Winston, OR 97496
      520 NW Tumlin Ave, Winston, OR 97496
      /19

      Est $286,606

      Not Listed For Sale

      520 NW Tumlin Ave, Winston, OR 97496

      • 3 Beds
      • 1 Bath
      • 1,234 Sq Ft
      • Built 1967
      520 NW Tumlin Ave, Winston, OR 97496

      Last Sold Summary

      • 63 Days On Market

  • 700 SE Tokay St, Winston, OR 97496
    700 SE Tokay St, Winston, OR 97496
    700 SE Tokay St, Winston, OR 97496
    /42

    $370,000

    Sold Mar 20, 2026

    700 SE Tokay St, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 2016

    Last Sold Summary

    • 4% Below List Price
    • $264/SF
    • 170 Days On Market

    Current Estimated Value $369,165

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

    700 SE Tokay St, Winston, OR 97496
    • 30 SE Darrell Ave, Winston, OR 97496
      30 SE Darrell Ave, Winston, OR 97496
      30 SE Darrell Ave, Winston, OR 97496
      /28

      Est $268,067

      Not Listed For Sale

      30 SE Darrell Ave, Winston, OR 97496

      • 3 Beds
      • 1 Bath
      • 1,180 Sq Ft
      • Built 1953
      30 SE Darrell Ave, Winston, OR 97496

      Last Sold Summary

      • 5 Days On Market

  • 765 SE Lanola St, Winston, OR 97496
    765 SE Lanola St, Winston, OR 97496
    765 SE Lanola St, Winston, OR 97496
    /28

    $389,000

    Sold Jul 03, 2025

    765 SE Lanola St, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,468 Sq Ft
    • Built 2016

    Last Sold Summary

    • $265/SF
    • 15 Days On Market

    Current Estimated Value $398,808

    Last Listing Agent Jacob Gilman The Neil Company Real Estate

    765 SE Lanola St, Winston, OR 97496
    • 160 SE Darrell Ave, Winston, OR 97496
      160 SE Darrell Ave, Winston, OR 97496
      160 SE Darrell Ave, Winston, OR 97496
      /16

      Est $189,183

      Not Listed For Sale

      160 SE Darrell Ave, Winston, OR 97496

      • 3 Beds
      • 1 Bath
      • 1,310 Sq Ft
      • Built 1951
      160 SE Darrell Ave, Winston, OR 97496

      Last Sold Summary

      • 179 Days On Market

  • 771 SE Hall St, Winston, OR 97496
    771 SE Hall St, Winston, OR 97496
    771 SE Hall St, Winston, OR 97496
    /48

    $255,000

    Sold May 15, 2026

    771 SE Hall St, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • Built 1997

    Last Sold Summary

    • 4% Below List Price
    • $155/SF
    • 21 Days On Market

    Current Estimated Value $253,656

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

    771 SE Hall St, Winston, OR 97496
    • 170 SE Darrell Ave, Winston, OR 97496
      170 SE Darrell Ave, Winston, OR 97496
      170 SE Darrell Ave, Winston, OR 97496
      /12

      Est $197,101

      Not Listed For Sale

      170 SE Darrell Ave, Winston, OR 97496

      • 2 Beds
      • 1 Bath
      • 1,158 Sq Ft
      • Built 1957
      170 SE Darrell Ave, Winston, OR 97496

      Last Sold Summary

      • 1 Day On Market

  • 310 NW Lost Ln, Winston, OR 97496
    310 NW Lost Ln, Winston, OR 97496
    310 NW Lost Ln, Winston, OR 97496
    /45

    $299,900

    Sold Jan 26, 2026

    310 NW Lost Ln, Winston, OR 97496

    • 4 Beds
    • 2 Baths
    • 1,769 Sq Ft
    • Built 1978

    Last Sold Summary

    • 9% Below List Price
    • $170/SF
    • 74 Days On Market

    Current Estimated Value $317,763

    Last Listing Agent Tammi Ellison eXp Realty, LLC

    310 NW Lost Ln, Winston, OR 97496
    • 71 SE Darrell Ave, Winston, OR 97496
      71 SE Darrell Ave, Winston, OR 97496
      71 SE Darrell Ave, Winston, OR 97496
      /21

      Est $276,040

      Not Listed For Sale

      71 SE Darrell Ave, Winston, OR 97496

      • 3 Beds
      • 1 Bath
      • 1,475 Sq Ft
      • Built 1952
      71 SE Darrell Ave, Winston, OR 97496

      Last Sold Summary

      • 99 Days On Market

  • 181 Lost Ln, Winston, OR 97496
    181 Lost Ln, Winston, OR 97496
    181 Lost Ln, Winston, OR 97496
    /26

    $379,000

    Sold Oct 03, 2025

    181 Lost Ln, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,279 Sq Ft
    • Built 2017

    Last Sold Summary

    • 10% Below List Price
    • $296/SF
    • 216 Days On Market

    Last Listing Agent Rachel Ball Triple Oaks Realty LLC

    181 Lost Ln, Winston, OR 97496
    • 53 SE Darrell Ave, Winston, OR 97496
      53 SE Darrell Ave, Winston, OR 97496
      53 SE Darrell Ave, Winston, OR 97496
      /5

      Est $293,939

      Not Listed For Sale

      53 SE Darrell Ave, Winston, OR 97496

      • 2 Beds
      • 1,608 Sq Ft
      • Built 1978
      53 SE Darrell Ave, Winston, OR 97496

      Last Sold Summary

      • 150 Days On Market

  • 431 NE Darlene St, Winston, OR 97496
    431 NE Darlene St, Winston, OR 97496
    431 NE Darlene St, Winston, OR 97496
    /46

    $190,000

    Sold Sep 26, 2025

    431 NE Darlene St, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Built 1989

    Last Sold Summary

    • 16% Below List Price
    • $117/SF
    • 23 Days On Market

    Current Estimated Value $237,078

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

    431 NE Darlene St, Winston, OR 97496
    • 10 NE Gregory Dr, Winston, OR 97496
      10 NE Gregory Dr, Winston, OR 97496
      10 NE Gregory Dr, Winston, OR 97496
      /20

      Est $297,976

      Not Listed For Sale

      10 NE Gregory Dr, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,556 Sq Ft
      • Built 1948
      10 NE Gregory Dr, Winston, OR 97496

      Last Sold Summary

      • 49 Days On Market

  • 235 NE Main St, Winston, OR 97496
    235 NE Main St, Winston, OR 97496
    235 NE Main St, Winston, OR 97496
    /48

    $418,000

    Sold Jul 25, 2025

    235 NE Main St, Winston, OR 97496

    • 4 Beds
    • 2.5 Baths
    • 1,808 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Above List Price
    • $231/SF
    • 10 Days On Market

    Current Estimated Value $430,432

    Last Listing Agent Julie Bancroft The Neil Company Real Estate

    235 NE Main St, Winston, OR 97496
    • 11 NE Hillside Ave, Winston, OR 97496
      11 NE Hillside Ave, Winston, OR 97496
      11 NE Hillside Ave, Winston, OR 97496
      /21

      Est $207,670

      Not Listed For Sale

      11 NE Hillside Ave, Winston, OR 97496

      • 2 Beds
      • 1 Bath
      • 866 Sq Ft
      • Built 1948
      11 NE Hillside Ave, Winston, OR 97496

      Last Sold Summary

      • 35 Days On Market

  • 645 SE Garden Way Dr, Winston, OR 97496
    645 SE Garden Way Dr, Winston, OR 97496
    645 SE Garden Way Dr, Winston, OR 97496
    /46

    $380,000

    Sold Mar 05, 2026

    645 SE Garden Way Dr, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,447 Sq Ft
    • Built 2019

    Last Sold Summary

    • 5% Below List Price
    • $263/SF
    • 17 Days On Market

    Current Estimated Value $378,762

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

    645 SE Garden Way Dr, Winston, OR 97496
    • 90 NE Ronald St, Winston, OR 97496
      90 NE Ronald St, Winston, OR 97496
      90 NE Ronald St, Winston, OR 97496
      /37

      Est $266,044

      Not Listed For Sale

      90 NE Ronald St, Winston, OR 97496

      • 3 Beds
      • 1 Bath
      • 1,116 Sq Ft
      • Built 1981
      90 NE Ronald St, Winston, OR 97496

      Last Sold Summary

      • 9 Days On Market

  • 110 SE Darrell Ave, Winston, OR 97496
    110 SE Darrell Ave, Winston, OR 97496
    110 SE Darrell Ave, Winston, OR 97496
    /22

    $183,300

    Sold Apr 08, 2026

    110 SE Darrell Ave, Winston, OR 97496

    • 2 Beds
    • 1 Bath
    • 735 Sq Ft
    • Built 1953

    Last Sold Summary

    • 12% Below List Price
    • $249/SF
    • 415 Days On Market

    Current Estimated Value $179,295

    Last Listing Agent Lacey Williams Trueblood Real Estate

    110 SE Darrell Ave, Winston, OR 97496
    • 450 Woodland Dr, Winston, OR 97496
      450 Woodland Dr, Winston, OR 97496
      450 Woodland Dr, Winston, OR 97496
      /48

      Est $618,333

      Not Listed For Sale

      450 Woodland Dr, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 2,651 Sq Ft
      • Built 1972
      450 Woodland Dr, Winston, OR 97496

      Last Sold Summary

      • 130 Days On Market

    • 1680 Byron Creek Rd, Winston, OR 97496
      1680 Byron Creek Rd, Winston, OR 97496
      1680 Byron Creek Rd, Winston, OR 97496
      /10

      Est $419,914

      Not Listed For Sale

      1680 Byron Creek Rd, Winston, OR 97496

      • 2 Beds
      • 1 Bath
      • 1,333 Sq Ft
      • Built 1985
      1680 Byron Creek Rd, Winston, OR 97496

      Last Sold Summary

      • 12 Days On Market

    • 1207 Willis Creek Rd, Winston, OR 97496
      1207 Willis Creek Rd, Winston, OR 97496
      1207 Willis Creek Rd, Winston, OR 97496
      /47

      Est $401,000

      Not Listed For Sale

      1207 Willis Creek Rd, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,782 Sq Ft
      • Built 1989
      1207 Willis Creek Rd, Winston, OR 97496

      Last Sold Summary

      • 195 Days On Market

    • 1069 Willis Creek Rd, Winston, OR 97496
      1069 Willis Creek Rd, Winston, OR 97496
      1069 Willis Creek Rd, Winston, OR 97496
      /34

      Est $417,000

      Not Listed For Sale

      1069 Willis Creek Rd, Winston, OR 97496

      • 5 Beds
      • 2 Baths
      • 2,374 Sq Ft
      • Built 1977
      1069 Willis Creek Rd, Winston, OR 97496

      Last Sold Summary

      • 49 Days On Market

    • 125 A Ave, Winston, OR 97496
      125 A Ave, Winston, OR 97496
      125 A Ave, Winston, OR 97496
      /27

      Est $227,425

      Not Listed For Sale

      125 A Ave, Winston, OR 97496

      • 3 Beds
      • 1 Bath
      • 1,118 Sq Ft
      • Built 1955
      125 A Ave, Winston, OR 97496

      Last Sold Summary

      • 1 Day On Market

Showing Results 241 - 280, Page 7 of 18

Oregon Douglas County Winston

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

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 © 2026 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.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group