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Winston, OR Homes for Sale — Page 2 | Realty.com
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3 beds
38 listings
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New construction
With a pool

Homes for Sale in Winston, OR

Homes for Sale in Winston, OR

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14 of 38 Listings
Map

Homes for Sale in Winston, OR

14 of 38 Listings

Your local brokerage

JJ

Jeffrey J Jonas

L. Custen Realty dba Realty.com

Lic. #200709170

Call Jeffrey
  1. 186 Woodduck St — photoPrice Reduced48Active

    $366,000

    3 bd · 2 ba · 1,613 sqft

    186 Woodduck St, Winston, OR

    Mary Gilbert · Keller Williams Southern Oregon-Umpqua Valley

  2. 101 SW Peach Ln — photoPrice Reduced22Active

    $299,000

    3 bd · 1 ba · 1,348 sqft

    101 SW Peach Ln, Winston, OR

    Joseph Hajos · Berkshire Hathaway HomeServices Real Estate Professionals

  3. 311 SE Grape Ave — photo36Active

    $459,000

    3 bd · 1 ba · 1,250 sqft

    311 SE Grape Ave, Winston, OR

    Mary Gilbert · Keller Williams Southern Oregon-Umpqua Valley

  4. 340 SE Darrell Ave — photoPrice Reduced26Active

    $270,000

    3 bd · 1 ba · 1,000 sqft

    340 SE Darrell Ave, Winston, OR

    Aaron Stansbury · Keller Williams Realty Eugene and Springfield

  5. 1349 Willis Creek Rd — photoPrice Reduced48Active

    $1,099,900

    3 bd · 3 ba · 2,856 sqft

    1349 Willis Creek Rd, Winston, OR

    Jordan Anderson · The Anderson Agency

  6. 380 NW Cary St — photoPrice Reduced34Active

    $350,000

    4 bd · 2 ba · 1,710 sqft

    380 NW Cary St, Winston, OR

    Willow Pearson · Oregon Life Homes

  7. 6700 Upper Olalla Rd — photoPrice Reduced48Active

    $1,050,000

    3 bd · 3 ba · 2,720 sqft

    6700 Upper Olalla Rd, Winston, OR

    Daniel Gandee · Real Broker

  8. 411 Woodland Dr — photoPrice Reduced44Active

    $680,000

    4 bd · 2 ba · 2,240 sqft

    411 Woodland Dr, Winston, OR

    Nataly Mattox · RE/MAX Integrity

  9. 90 SE Darrell Ave — photoPrice Reduced15Active

    $205,000

    2 bd · 2 ba · 924 sqft

    90 SE Darrell Ave, Winston, OR

    Rebekah Sexauer · eXp Realty, LLC

  10. 160 Wil Way — photoPrice Reduced41Active

    $499,900

    3 bd · 3 ba · 2,089 sqft

    160 Wil Way, Winston, OR

    Tyler Head · Turning Point Realty Group

  11. 150 Wil Way — photoPrice Reduced40Active

    $499,900

    3 bd · 3 ba · 1,999 sqft

    150 Wil Way, Winston, OR

    Tyler Head · Turning Point Realty Group

  12. 124 Country Side Ln — photoPrice Reduced23Active

    $60,000

    3 bd · 2 ba · 1,296 sqft

    124 Country Side Ln, Winston, OR

    Jason Mann · J Mann Realty

  13. 1941 Byron Creek Rd — photoPrice Reduced48Active

    $469,900

    2 bd · 2 ba · 1,764 sqft

    1941 Byron Creek Rd, Winston, OR

    Andrew Stoner · Roseburg Realty

  14. 80 NW Lost Ln — photo4Active

    $2,000,000

    4 bd · 2 ba · 1,992 sqft

    80 NW Lost Ln, Winston, OR

    Dawn Trapalis · Harcourts Integrity Team Real Estate Services, LLC.

12

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Regional Multiple Listing Service (RMLS)
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Listing information ©2026 RMLS™ of Portland, Oregon.Inc®. All Rights Reserved. Last Updated: 2026-09-12 07:13:41 UTC
    • New construction
    • With a pool

    Your local brokerage

    JJ

    Jeffrey J Jonas

    L. Custen Realty dba Realty.com

    Lic. #200709170

    Call Jeffrey

    Nearby areas

    ZIP codes

    • 97471 (176)
    • 97470 (97)
    • 97457 (57)
    • 97479 (50)
    • 97496 (38)
    • 97443 (20)
    • 97410 (19)
    • 97469 (17)

    Cities

    • Roseburg (273)
    • MyrtleCreek (57)
    • Sutherlin (50)
    • Glide (20)
    • Azalea (19)
    • Riddle (17)
    • Oakland (15)
    • Canyonville (11)

    Winston, OR community profile

    Population
    5,764
    Median income
    $54,278
    Housing units
    2,546
    People per sq. mi.
    42.7
    Area
    135.1 sq. mi.

    Source: HJN community data

    Winston housing market

    August 2026

    Winston 12-month median sale price trend

    Selling at 99.0% of asking price

    Buyers here are paying below asking. MLS · 11 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 26, 2026

    Median sale price
    $318,000$244,765–$400,250 typical range
    Price per sq. ft.
    $218
    Sales
    14
    Paid in cash
    57.1%

    Homes on the market · MLS, as of Aug 31, 2026

    Median list price
    $420,000
    Homes for sale
    39
    Median days on market
    42 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    -14.6%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    1,429 sq. ft.