3,191

Winston, OR Homes

Section Image
  • /31

    $285,000

    Sold Mar 13, 2026

    271 NW Sherry St, Winston, OR 97496

    • 3 Beds
    • 1 Bath
    • 1,260 Sq Ft
    • Built 1966

    Last Sold Summary

    • $226/SF
    • 26 Days On Market

    Current Estimated Value $282,128

    Last Listing Agent Shae Ellison Platinum Realty

    271 NW Sherry St, 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

      • 102 Days On Market

  • /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
  • /20

    $50,000

    Sold Jun 01, 2026

    271 SE Robinson St, Winston, OR 97496

    • Land
    • 5,227 Sq Ft
    • $416,667 per Acre

    Last Sold Summary

    • 44% Below List Price
    • 201 Days On Market

    Current Estimated Value $78,800

    Last Listing Agent Kayla Wehe Lamonte Real Estate Professionals

    271 SE Robinson St, Winston, OR 97496
    • /38

      Est $423,890

      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

      • 15 Days On Market

  • /15

    $149,900

    Pending
    • 2 Beds
    • 2 Baths
    • 1,130 Sq Ft

    463 SE Gregory Dr, Winston, OR 97496

    Clean comfy 1993 manufactured home with factory built addition. Has 1130 sq ft with deck. On .21 acre lot. 3 br 2 baths. Includes range, refrig, microwave, dishwasher, trash compactor, washer/dryer. Assumable VA loan. Has playhouse and storage building. Financeable; conv, FHA, VA.

    Valynn Currie Currieco Real Estate

    463 SE Gregory Dr, Winston, OR 97496
  • /7

    $150,000

    Sold Aug 08, 2025

    0 Ireland Rd, Winston, OR 97496

    • Land
    • 32.74 Acres
    • $4,582 per Acre

    Last Sold Summary

    • 15% Above List Price
    • 89 Days On Market

    Last Listing Agent Daniel Siler Engel & Volkers West Portland

    0 Ireland Rd, Winston, OR 97496
    • /23

      Est $239,580

      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

      • 61 Days On Market

  • /41

    $830,000

    $40K PRICE DROP Under Contract
    • 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
  • /23

    $117,500

    Sold May 05, 2026

    221 NW Bree Dr, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,377 Sq Ft
    • Built 1998

    Last Sold Summary

    • 1% Below List Price
    • $85/SF
    • 3 Days On Market

    Last Listing Agent Brenda Smith Stellar Realty Northwest

    221 NW Bree Dr, 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

  • /2

    Call for Price

    Pending
    • Land
    • 160 Acres

    0 Diamond Rock Rd Unit 727456026, Winston, OR 97496

    160± acre Diamond Rock Road Recreation and Timber Tract is located within Umpqua National Forest, six miles south of South Umpqua River community of Tiller, and two miles from Drew at County Road 1. Diamond Rock Road (FS3201 Road) provides access to Drew, and continues through the Tract south, to both private and USFS lands. The entire Tract was impacted by 2015 Stouts Fire, and was replanted

    John Rosenthal Realty Marketing / Northwest

    0 Diamond Rock Rd Unit 727456026, Winston, OR 97496
  • /21

    $355,000

    Sold Sep 18, 2025

    595 SE Parkway Dr, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,348 Sq Ft
    • Built 1996

    Last Sold Summary

    • 1% Below List Price
    • $263/SF
    • 8 Days On Market

    Current Estimated Value $368,213

    Last Listing Agent Jacob Gilman The Neil Company Real Estate

    595 SE Parkway Dr, Winston, OR 97496
    • /48

      Est $924,746

      Not Listed For Sale

      6910 Upper Olalla Rd, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 3,564 Sq Ft
      • Built 2012
      6910 Upper Olalla Rd, Winston, OR 97496

      Last Sold Summary

      • 151 Days On Market

  • /15

    $165,000

    $15K 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
  • /27

    $273,000

    Sold May 13, 2026

    151 NE Plum Ridge Dr, Winston, OR 97496

    • 4 Beds
    • 2.5 Baths
    • 1,512 Sq Ft
    • Built 2005

    Last Sold Summary

    • 5% Below List Price
    • $181/SF
    • 44 Days On Market

    Current Estimated Value $297,268

    Last Listing Agent Tiffanie Frasier Keller Williams Southern Oregon-Umpqua Valley

    151 NE Plum Ridge Dr, Winston, OR 97496
    • /45

      Est $417,410

      Not Listed For Sale

      291 SE Kara St, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,577 Sq Ft
      • Built 2022
      291 SE Kara St, Winston, OR 97496

      Last Sold Summary

      • 0 Days On Market

  • /30

    $205,000

    • 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
  • /10

    $255,000

    Sold Nov 12, 2025

    829 Raleigh Dr, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 2003

    Last Sold Summary

    • 4% Below List Price
    • $197/SF
    • 1 Day On Market

    Current Estimated Value $251,031

    Last Listing Agent Kayla Wehe Lamonte Real Estate Professionals

    829 Raleigh Dr, Winston, OR 97496
    • /11

      Not Listed For Sale

      0 Wil Way Unit 24000784, Winston, OR 97496

      0 Wil Way Unit 24000784, Winston, OR 97496

      Last Sold Summary

      • 15 Days On Market

  • /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
  • /27

    $315,000

    Sold Feb 27, 2026

    120 SE Edwards Ave, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,421 Sq Ft
    • Built 2005

    Last Sold Summary

    • 10% Below List Price
    • $222/SF
    • 194 Days On Market

    Current Estimated Value $325,999

    Last Listing Agent Jerry Norman Oregon Life Homes

    120 SE Edwards Ave, Winston, OR 97496
    • /22

      Est $323,070

      Not Listed For Sale

      109 NW Woodland Dr, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,386 Sq Ft
      • Built 2023
      109 NW Woodland Dr, Winston, OR 97496

      Last Sold Summary

      • 85 Days On Market

  • /34

    $355,000

    $4K 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
  • /21

    $190,000

    Sold Jun 11, 2026

    751 SE Meadowood Dr, Winston, OR 97496

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1995

    Last Sold Summary

    • 21% Below List Price
    • $170/SF
    • 100 Days On Market

    Current Estimated Value $183,408

    Last Listing Agent Timothy A Smith RE/MAX Integrity

    751 SE Meadowood Dr, Winston, OR 97496
    • /18

      Est $300,182

      Not Listed For Sale

      220 NW Timothy Ave, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,188 Sq Ft
      • Built 2000
      220 NW Timothy Ave, Winston, OR 97496

      Last Sold Summary

      • 13 Days On Market

  • /47

    $380,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,352 Sq Ft

    421 NW Cary St, Winston, OR 97496

    Immaculate Charmer. Tucked away on an expansive fully fenced 1/2 acre corner lot, this stellar turn-key property blends timeless comfort with stylish modern updates in a setting designed to truly feel like home. Every detail has been thoughtfully curated to create warmth, functionality, and charm.Step inside to discover spacious living areas filled with natural light, including both a living room

    Tammi Ellison eXp Realty, LLC

    421 NW Cary St, Winston, OR 97496
  • /23

    $110,000

    Sold Oct 16, 2025

    260 NE Darrell Ave, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,381 Sq Ft
    • Built 1989

    Last Sold Summary

    • 19% Below List Price
    • $80/SF
    • 24 Days On Market

    Current Estimated Value $95,500

    Last Listing Agent Lacey Williams Trueblood Real Estate

    260 NE Darrell Ave, Winston, OR 97496
    • /16

      Est $329,544

      Not Listed For Sale

      692 SE Lenore St, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,295 Sq Ft
      • Built 2006
      692 SE Lenore St, Winston, OR 97496

      Last Sold Summary

      • 101 Days On Market

  • /17

    $550,000

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft

    572 Dillard Gardens Rd, Winston, OR 97496

    Charming property on the South Umpqua River features a 1,440 sf home set on 6.9 acres. The 2-bed 2-bath interior includes wood floors, an open living room with a fireplace insert, an open kitchen, large primary bedroom with an ensuite bath, laundry room and covered deck. Back patio and yard area is peaceful and quiet with flowers and shade trees. New septic system was installed in 2021. Detached

    Mike Nichols MORE Realty, Inc.

    572 Dillard Gardens Rd, Winston, OR 97496
  • /41

    $650,000

    Sold Aug 08, 2025

    1260 Ireland Rd, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 2,600 Sq Ft
    • Built 2016

    Last Sold Summary

    • 35% Below List Price
    • $250/SF
    • 89 Days On Market

    Current Estimated Value $622,000

    Last Listing Agent Daniel Siler Engel & Volkers West Portland

    1260 Ireland Rd, Winston, OR 97496
    • /13

      Not Listed For Sale

      280 NW Bree Dr, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1998
      280 NW Bree Dr, Winston, OR 97496

      Last Sold Summary

      • 211 Days On Market

  • /32

    $530,000

    Open Sat 11AM - 1PM $79K PRICE DROP
    • 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 hard wood floors, 2 gas fireplaces, central vac, top quality custom elegant crown molding. Formal dining, gourmet kitchen, spacious gazebo/pergola, colored stamped concrete, sprinkler system, fenced manicured private backyard with raised beds. Has new astro turf for low maintenance front yard, covered patio. The gourmet kitchen has

    Valynn Currie Currieco Real Estate

    102 Sarah Bear Ln, Winston, OR 97496
  • /35

    $465,000

    Sold Jul 15, 2025

    271 Woodland Dr, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,754 Sq Ft
    • Built 1965

    Last Sold Summary

    • $265/SF
    • 22 Days On Market

    Current Estimated Value $464,419

    Last Listing Agent Patrice Glasscock Walt Gayner Real Estate

    271 Woodland Dr, Winston, OR 97496
    • /37

      Est $440,706

      Not Listed For Sale

      122 Citation Ct, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,564 Sq Ft
      • Built 2023
      122 Citation Ct, Winston, OR 97496

      Last Sold Summary

      • 78 Days On Market

  • /39

    $290,000

    Pending
    • 4 Beds
    • 2 Baths
    • 1,782 Sq Ft

    70 SE Darrell Ave, Winston, OR 97496

    Stunning newly remodeled manufactured home tucked away in a private neighborhood in Winston! This spacious 4 bed, 2 bath home features a desirable split floor plan with vaulted ceilings and bright natural light throughout.Completely updated from top to bottom with new flooring, fresh interior and exterior paint, new windows, doors, carpet, and a brand-new roof. The main bathroom has been

    Shae Ellison Platinum Realty

    70 SE Darrell Ave, Winston, OR 97496
  • /47

    $270,000

    Sold Apr 20, 2026

    430 SE Carrol St, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,249 Sq Ft
    • Built 1957

    Last Sold Summary

    • 1% Above List Price
    • $216/SF
    • 53 Days On Market

    Current Estimated Value $267,893

    Last Listing Agent Elena Mackey eXp Realty, LLC

    430 SE Carrol St, Winston, OR 97496
    • /13

      Not Listed For Sale

      434 NW Broc Dr, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,173 Sq Ft
      • Built 2024
      434 NW Broc Dr, Winston, OR 97496

      Last Sold Summary

      • 162 Days On Market

  • /11

    $179,000

    $40K PRICE DROP
    • 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
  • /20

    $1,230,000

    Sold Oct 16, 2025

    Unlisted Address

    • Land
    • 609.6 Acres
    • $2,018 per Acre

    Last Sold Summary

    • 25% Below List Price
    • 786 Days On Market

    Last Listing Agent Tim Snyder Berkshire Hathaway HomeServices Real Estate Professionals

    Unlisted Address

Showing Results 81 - 120, Page 3 of 18

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