3,178

Winston, OR Homes

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  • /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
  • /45

    $255,000 Sold Mar 20, 2026

    308 NW Civil Bend Ave, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1996

    Last Sold Summary

    • 4% Below List Price
    • $197/SF
    • 102 Days On Market

    Current Estimated Value $254,961

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

    308 NW Civil Bend Ave, Winston, OR 97496
    • /48

      Est $694,532 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

      • 37% Below List Price
      • $311/SF
      • 151 Days On Market

      Last Sold Price $1,109,000

      Last Listing Agent Rachel Bryant Keller Williams Southern Oregon-Umpqua Valley

  • /20

    $80,000

    • Land
    • 0.12 Acre
    • $666,667 per Acre

    271 SE Robinson St, Winston, OR 97496

    Build Your Dream Home on This Prime Lot!Nice Lot – Prime Location – All Utilities – Investment Opportunity!Discover the perfect canvas for your future home. This spacious lot comes with full utilities—water, electricity, and sewer—ready for you to build. Nestled in a good location, it’s ideal for families, investors, or anyone looking to live in town. Don’t miss out on this incredible

    Kayla Wehe Lamonte Real Estate Professionals

    271 SE Robinson St, Winston, OR 97496
  • /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 $282,459

    Last Listing Agent Shae Ellison Platinum Realty

    271 NW Sherry St, Winston, OR 97496
    • /45

      Est $416,649 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

      • 2% Above List Price
      • $258/SF
      • 0 Days On Market

      Last Sold Price $407,500

      Last Listing Agent Codi Lookabaugh Redfin

  • /11

    $312,000

    • Land
    • 13.5 Acres
    • $23,111 per Acre

    0 NW Brockway Rd, Winston, OR 97496

    Premier 13.5 Mixed-Use Development Opportunity! A trifecta of buildability and prestige. Position your next project in the path of progress with this exceptional parcel. Located strategically within the Urban Growth Area and zoned as mixed use (CHIS), this site offers density potential combined with the unparalleled natural beauty of the region which include mountain and vineyard views. The

    Cynthia Beach The Neil Company Real Estate

    0 NW Brockway Rd, 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
    • /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

      Last Sold Price $200,000

      Last Listing Agent Marilyn Kittelman Cutting Edge Real Estate

  • /15

    $149,900

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

    463 SE Gregory Dr, Winston, OR 97496

    1993 manufactured home with 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.

    Valynn Currie Currieco Real Estate

    463 SE Gregory Dr, 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 $355,910

    Last Listing Agent Jacob Gilman The Neil Company Real Estate

    595 SE Parkway Dr, Winston, OR 97496
    • /22

      Est $332,926 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

      • 8% Above List Price
      • $223/SF
      • 85 Days On Market

      Last Sold Price $309,000

      Last Listing Agent Julie Lauritzen Oregon Life Homes

  • /23

    $119,000

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

    221 NW Bree Dr, Winston, OR 97496

    Meticulously maintained 3-bedroom, 2-bath manufactured home located in a quiet and private all-ages co-op community with a low $449 monthly space rent, including water and sewer. Built in 1998, this home offers a functional and inviting layout with a split-bedroom design and a separate family/media room just off the main living area, providing flexibility for everyday living or entertaining. The

    Brenda Smith Stellar Realty Northwest

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

    $469,900 Sold Apr 16, 2025

    117 Citation Ct, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,679 Sq Ft
    • Built 2024

    Last Sold Summary

    • 2% Above List Price
    • $280/SF
    • 16 Days On Market

    Current Estimated Value $474,945

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

    117 Citation Ct, Winston, OR 97496
    • /18

      Est $308,885 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

      • 7% Above List Price
      • $243/SF
      • 13 Days On Market

      Last Sold Price $289,000

      Last Listing Agent Eloise Donovan Currieco Real Estate

  • /41

    $830,000 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
  • /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 $261,986

    Last Listing Agent Kayla Wehe Lamonte Real Estate Professionals

    829 Raleigh Dr, Winston, OR 97496
    • /16

      Est $319,825 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

      • 2% Above List Price
      • $243/SF
      • 101 Days On Market

      Last Sold Price $315,000

      Last Listing Agent Scott Welch More Realty

  • /15

    $180,000

    • 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

    $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 $321,750

    Last Listing Agent Jerry Norman Oregon Life Homes

    120 SE Edwards Ave, 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

      • $56/SF
      • 211 Days On Market

      Last Sold Price $67,500

      Last Listing Agent Jeff Boyter The Neil Company Real Estate

  • /27

    $273,000 Pending

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

    151 NE Plum Ridge Dr, Winston, OR 97496

    Spacious 4 bedroom, 2.5 bath home located in the Plum Ridge neighborhood of Winston. 1512 sq ft with a functional floor plan, open living and dining area, and generous bedroom sizes. Detached 2-car garage and fenced yard provide added utility and storage. Bring your tools and get ready to build equity with this light-fix opportunity. Home is in need of repairs and updating and is being sold in

    Tiffanie Frasier Keller Williams Southern Oregon-Umpqua Valley

    151 NE Plum Ridge Dr, 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 $124,396

    Last Listing Agent Lacey Williams Trueblood Real Estate

    260 NE Darrell Ave, Winston, OR 97496
    • /37

      Est $423,726 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

      • 3% Above List Price
      • $262/SF
      • 78 Days On Market

      Last Sold Price $409,900

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

  • /47

    $268,000 Pending

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

    430 SE Carrol St, Winston, OR 97496

    Beautifully updated 3-bedroom, 2-bath Craftsman-style home situated on a corner lot in a charming small town. The home features a great open floor plan with a dedicated dining area, highlighted by a beautiful custom maple eating bar that adds unique character and warmth. The spacious living room showcases brand-new laminate flooring and a cozy pellet stove, providing comfort and relaxation during

    Elena Mackey eXp Realty, LLC

    430 SE Carrol St, 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 $708,000

    Last Listing Agent Daniel Siler Engel & Volkers West Portland

    1260 Ireland Rd, 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

      • $115/SF
      • 162 Days On Market

      Last Sold Price $135,000

      Last Listing Agent Katy Bernal Bernal Realtor LLC

  • /22

    $375,000 Open House 4/11

    • 3 Beds
    • 2 Baths
    • 1,452 Sq Ft

    182 Woodduck St, Winston, OR 97496

    Quality contemporary 3 bedroom, 2 bath 1452 sq ft home built in 2005 in Hunters Crossing. Has Double garage, vaulted ceilings, appliances included. Newly painted. Laminate floors throughout, covered patio in private fenced yard low maintenance. Will finance all ways. Turn key ready. RV Parking/boat parking.

    Valynn Currie Currieco Real Estate

    182 Woodduck St, 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 $460,219

    Last Listing Agent Patrice Glasscock Walt Gayner Real Estate

    271 Woodland Dr, Winston, OR 97496
    • /31

      Est $427,062 Not Listed For Sale

      120 Citation Ct, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,679 Sq Ft
      • Built 2023
      120 Citation Ct, Winston, OR 97496

      Last Sold Summary

      • $255/SF
      • 2 Days On Market

      Last Sold Price $427,500

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

  • /34

    $359,000 Open House 4/11

    • 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
  • /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
    • /43

      Est $303,898 Not Listed For Sale

      189 SE Darrell Ave, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,323 Sq Ft
      • Built 2023
      189 SE Darrell Ave, Winston, OR 97496

      Last Sold Summary

      • 10% Above List Price
      • $209/SF
      • 79 Days On Market

      Last Sold Price $276,000

      Last Listing Agent Mark Townsend Keller Williams Southern Oregon-Umpqua Valley

  • /37

    $353,400 Pending

    • 3 Beds
    • 2 Baths
    • 1,290 Sq Ft

    110 Teresa Ln, Winston, OR 97496

    Welcome home to this beautifully maintained single-level residence in the sought-after Creekside Meadows neighborhood of Winston. Built in 2018, this light-filled 3-bedroom, 2-bath home offers 1,290 square feet of thoughtfully designed living space with an open, easy-flow floor plan ideal for both everyday living and entertaining. Vinyl flooring runs throughout the home, complementing the modern

    TAYLOR CAMPBELL Urban Pacific Real Estate

    110 Teresa Ln, Winston, OR 97496
  • /37

    $407,000 Sold Jan 26, 2026

    5979 Willis Creek Rd, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Built 1977

    Last Sold Summary

    • 3% Above List Price
    • $251/SF
    • 13 Days On Market

    Current Estimated Value $369,842

    Last Listing Agent Jody Tatone RE/MAX Integrity

    5979 Willis Creek Rd, Winston, OR 97496
    • /26

      Est $381,316 Not Listed For Sale

      205 Lebleu Ln, Winston, OR 97496

      • 4 Beds
      • 3 Baths
      • 1,740 Sq Ft
      • Built 2005
      205 Lebleu Ln, Winston, OR 97496

      Last Sold Summary

      • 5% Above List Price
      • $209/SF
      • 98 Days On Market

      Last Sold Price $364,000

      Last Listing Agent Deleta Dickson eXp Realty, LLC

  • /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
  • /43

    $299,000 Sold Aug 27, 2025

    200 SE Darrell Ave, Winston, OR 97496

    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft
    • Built 2025

    Last Sold Summary

    • 4% Below List Price
    • $227/SF
    • 36 Days On Market

    Current Estimated Value $294,518

    Last Listing Agent Jennifer Kramer RE/MAX Integrity

    200 SE Darrell Ave, Winston, OR 97496
    • /32

      Not Listed For Sale

      1939 Byron Creek Rd, Winston, OR 97496

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 2011
      1939 Byron Creek Rd, Winston, OR 97496

      Last Sold Summary

      • $252/SF
      • 30 Days On Market

      Last Sold Price $327,000

      Last Listing Agent Julie Bancroft The Neil Company Real Estate

  • /23

    $90,000

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

    124 Country Side Ln, Winston, OR 97496

    Welcome home to this charming home located in a beautifully maintained 55+ community! With 3 bedrooms, 2 baths, and 1,296 sq. ft. of inviting living space, this home features vaulted ceilings, a bright open layout, and a manicured corner lot. The walk-through kitchen includes a breakfast bar, built-in microwave, stove, refrigerator, and a brand-new dishwasher. The spacious primary suite offers

    Jason Mann J Mann Realty

    124 Country Side Ln, Winston, OR 97496

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