Winston, OR Homes

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  /27

  $357,900

  • 3 Beds
  • 2 Baths
  • 1,433 Sq Ft

  380 SE Sunnyside Dr, Winston, OR 97496

  Welcome to 380 Sunnyside! This move-in-ready 3-bedroom, 2-bath home offers comfort, quality updates, and everyday convenience. Vaulted ceilings and peaceful territorial views create a bright, open feel from the moment you step inside. Recent upgrades include fresh interior paint, brand-new LVP flooring, and a newly built spacious deck, giving the home a modern look without the new construction

  

  Rockwell Group

  eXp Realty, LLC

  (458) 224-8911

  380 SE Sunnyside Dr, Winston, OR 97496
• Explore Winston

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  /9

  $1,300 per month

  • 2 Beds
  • 1 Bath
  • 1,600 Sq Ft
  • House for Rent

  160 Rose Ave, Winston, OR 97496

  Property Id: 6334192 BD 1 BTH vinyl wood plank flooring throughout, grassy fenced front yard. All new paint on the interior. All utilities except power included (trash, sewer, water, and wifi!) It is located in front of our storage facility and across from the Winston Police Department. Small pet considered, credit check, background check and references required. Please fill out

  160 Rose Ave, Winston, OR 97496
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  /9

  $185,000 Sold Oct 06, 2025

  50 NE Ronald St, Winston, OR 97496

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft
  • Built 1951

  Last Sold Summary

  • 1% Above List Price
  • $168/SF
  • 5 Days On Market

  Current Estimated Value $200,834

  Last Listing Agent Jody Tatone RE/MAX Integrity

  

  50 NE Ronald St, Winston, OR 97496
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  /22

  Not Listed For Sale

  338 NW Broc Dr, Winston, OR 97496

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1999

  

  338 NW Broc Dr, Winston, OR 97496

  Last Sold Summary

  • $86/SF
  • 32 Days On Market

  Last Sold Price $112,000

  Last Listing Agent Rachel Sturdevant eXp Realty, LLC
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  /28

  $350,000

  • Land
  • 7.4 Acres
  • $47,297 per Acre

  0 Wil Way Unit 24094727, Winston, OR 97496

  Rare investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Property has already been approved to be partitioned as either 2 larger parcels or a 28 lot subdivision! Currently no HOA or CC&Rs! Utilities conveniently are available nearby ready to be connected. The 2 parcels are also listed separately. Make an offer today before one or all

  

  Ashton Faas

  Different Better Real Estate

  (458) 310-3411

  

  0 Wil Way Unit 24094727, Winston, OR 97496
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  /7

  $876 per month

  • 1 Bed
  • 1 Bath
  • Apartment for Rent

  189 NW Glenhart Ave, Winston, OR 97496

  Rick Rivera Rental Housing Deals

  189 NW Glenhart Ave, Winston, OR 97496
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  /30

  $325,000 Sold Dec 31, 2025

  119 Lebleu Ln, Winston, OR 97496

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 2025

  Last Sold Summary

  • $322/SF
  • 59 Days On Market

  Current Estimated Value $323,103

  Last Listing Agent Benjamin Tatone Roseburg Realty

  

  119 Lebleu Ln, Winston, OR 97496
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  /27

  Est $262,820 Not Listed For Sale

  415 NW Apollo Ct, Winston, OR 97496

  • 3 Beds
  • 1 Bath
  • 1,088 Sq Ft
  • Built 1994

  

  415 NW Apollo Ct, Winston, OR 97496

  Last Sold Summary

  • 1% Above List Price
  • $239/SF
  • 6 Days On Market

  Last Sold Price $259,900

  Last Listing Agent Bob Lamonte Lamonte Real Estate Professionals
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  /15

  $185,000

  • Land
  • 3.14 Acres
  • $58,917 per Acre

  0 Wil Way Unit 24278136, Winston, OR 97496

  Great investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Currently no HOA or CC&Rs! Property has already been approved to be partitioned as a larger parcel or a over a dozen lot subdivision! Utilities conveniently are available nearby ready to be connected. The other parcel is also listed separately. Or both properties are available

  

  Ashton Faas

  Different Better Real Estate

  (458) 224-5797

  

  0 Wil Way Unit 24278136, Winston, OR 97496
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  /43

  $165,000 Sold Jun 25, 2025

  600 SE Edgewood St, Winston, OR 97496

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

  Last Sold Summary

  • 11% Below List Price
  • $206/SF
  • 52 Days On Market

  Current Estimated Value $135,500

  Last Listing Agent Elisa Doudna Pacific Properties

  

  600 SE Edgewood St, Winston, OR 97496
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  /19

  Est $342,046 Not Listed For Sale

  148 NE Rose Ridge Dr, Winston, OR 97496

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • Built 2004

  

  148 NE Rose Ridge Dr, Winston, OR 97496

  Last Sold Summary

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

  Last Sold Price $336,000

  Last Listing Agent Brittney Freamon River Valley Realty LLC
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  /15

  $185,000

  • Land
  • 4.26 Acres
  • $43,427 per Acre

  0 Wil Way Unit 24292479, Winston, OR 97496

  Unique investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Currently no HOA or CC&Rs! Property has already been approved to be partitioned as a larger parcel or a over a dozen lot subdivision! Utilities conveniently are available nearby ready to be connected. The other parcel is also listed separately. Or both properties are available

  

  Ashton Faas

  Different Better Real Estate

  (458) 217-1693

  

  0 Wil Way Unit 24292479, Winston, OR 97496
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  /18

  $240,000 Sold Aug 15, 2025

  563 Medicine Wheel Way, Winston, OR 97496

  • 2 Beds
  • 1 Bath
  • 1,111 Sq Ft
  • Built 1978

  Last Sold Summary

  • 11% Below List Price
  • $216/SF
  • 10 Days On Market

  Current Estimated Value $236,673

  Last Listing Agent Shea Wheeler RE/MAX Integrity

  

  563 Medicine Wheel Way, Winston, OR 97496
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  /6

  Est $575,341 Not Listed For Sale

  13450 Lookingglass Rd, Winston, OR 97496

  • 4 Beds
  • 2 Baths
  • 2,280 Sq Ft
  • Built 1909

  

  13450 Lookingglass Rd, Winston, OR 97496

  Last Sold Summary

  • 5% Above List Price
  • $241/SF
  • 214 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Ryan Kelly Whitetail Properties Real Estate LLC
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  /45

  $679,900

  • 4 Beds
  • 3.5 Baths
  • 3,072 Sq Ft

  635 Wil Way, Winston, OR 97496

  One of a kind property that is a true gem. Panoramic views of the Abacela Vineyards, the Wildlife Safari, the beautiful city, and the stunning valleys. While being tucked away at the end of the road for extra privacy. Nestled on over 20 acres, this parcel adjoins the Wildlife Safari. Imagine watching exotic animals from your back yard! The home is a gorgeous 2019 build featuing many high quality

  

  Ashton Faas

  Different Better Real Estate

  (458) 232-3589

  

  635 Wil Way, Winston, OR 97496
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  /7

  $148,000 Sold Mar 19, 2026

  31 SE Darrell Ave, Winston, OR 97496

  • 1 Bed
  • 1 Bath
  • 978 Sq Ft
  • Built 1954

  Last Sold Summary

  • 3% Below List Price
  • $151/SF
  • 12 Days On Market

  Current Estimated Value $152,774

  Last Listing Agent Judith Zuver Winston Realty & Insurance

  

  31 SE Darrell Ave, Winston, OR 97496
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  /44

  Not Listed For Sale

  127 Country Side Ln, Winston, OR 97496

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 2008

  

  127 Country Side Ln, Winston, OR 97496

  Last Sold Summary

  • $63/SF
  • 2 Days On Market

  Last Sold Price $95,000

  Last Listing Agent Tracy Grubbs eXp Realty, LLC
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  /23

  $55,000

  • 1 Bed
  • 1 Bath
  • 384 Sq Ft

  119 Oak Leaf Ln, Winston, OR 97496

  Affordable living in a quiet 55+ community! This cozy 1-bedroom, 1-bath manufactured home offers a functional layout and easy, low-maintenance living. The kitchen comes equipped with a free-standing range and refrigerator, both included in the sale. Located in a peaceful, well-kept neighborhood with a friendly community atmosphere. Conveniently situated near local amenities while maintaining a

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  119 Oak Leaf Ln, Winston, OR 97496
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  /30

  $99,900 Sold Jul 14, 2025

  311 Bremner Ln, Winston, OR 97496

  • 2 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2005

  Last Sold Summary

  • $84/SF
  • 34 Days On Market

  Last Listing Agent Cindi Mills RE/MAX Integrity

  

  311 Bremner Ln, Winston, OR 97496
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  /17

  Not Listed For Sale

  123 Twin Oaks Loop, Winston, OR 97496

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 1995

  

  123 Twin Oaks Loop, Winston, OR 97496

  Last Sold Summary

  • $95/SF
  • 20 Days On Market

  Last Sold Price $103,000

  Last Listing Agent Jeff Boyter The Neil Company Real Estate
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  /45

  $66,000

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  125 SE Estate Loop, Winston, OR 97496

  Take in breathtaking views of Umpqua Valley and the surrounding mountains from this spacious manufactured home located in a welcoming 55+ community. Unwind on the large covered front porch. Featuring a metal roof, double-pane vinyl windows, and a sturdy concrete block foundation, this home offers lasting durability. Stay comfortable year-round with the newer heat pump installed in 2022.

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  125 SE Estate Loop, Winston, OR 97496
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  /46

  $290,000 Sold Jul 18, 2025

  400 SE Darrell Ave, Winston, OR 97496

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1940

  Last Sold Summary

  • 1% Above List Price
  • $242/SF
  • 36 Days On Market

  Current Estimated Value $280,633

  Last Listing Agent Sabrina Jorgensen Fathom Realty Oregon, LLC

  

  400 SE Darrell Ave, Winston, OR 97496
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  /32

  Est $347,718 Not Listed For Sale

  220 NE Rose Ridge Dr, Winston, OR 97496

  • 3 Beds
  • 2.5 Baths
  • 1,586 Sq Ft
  • Built 2004

  

  220 NE Rose Ridge Dr, Winston, OR 97496

  Last Sold Summary

  • 11% Above List Price
  • $198/SF
  • 67 Days On Market

  Last Sold Price $314,000

  Last Listing Agent Julie Bancroft The Neil Company Real Estate
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  /48

  $265,000 Open Fri 2PM - 4PM

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

  771 SE Hall St, Winston, OR 97496

  Welcome to 771 SE Hall St in Winston where comfort meets convenience in this spacious 3 bedroom 2 bath home featuring 1650 square feet of well designed living space on a 0.16 acre lot. Curb appeal abounds with a freshly painted covered front porch and an expansive driveway providing tons of parking for vehicles or recreational toys. Peace of mind comes included with a newer roof and a newer hot

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  771 SE Hall St, Winston, OR 97496
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  /27

  $407,000 Sold Dec 19, 2025

  631 SE Rose Ridge Dr, Winston, OR 97496

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 2020

  Last Sold Summary

  • 5% Below List Price
  • $269/SF
  • 74 Days On Market

  Current Estimated Value $398,513

  Last Listing Agent Jacob Gilman The Neil Company Real Estate

  

  631 SE Rose Ridge Dr, Winston, OR 97496
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  /34

  Not Listed For Sale

  224 NW Bree Dr, Winston, OR 97496

  • 4 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 1998

  

  224 NW Bree Dr, Winston, OR 97496

  Last Sold Summary

  • $71/SF
  • 3 Days On Market

  Last Sold Price $115,000

  Last Listing Agent Deleta Dickson eXp Realty, LLC
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  /36

  $409,000

  • 7 Beds
  • 4.5 Baths
  • 3,861 Sq Ft

  2414 Brockway Rd, Winston, OR 97496

  Opportunity awaits! Whether you’re a savvy investor seeking passive income, a large family looking for a multi-generational setup, or a single household wanting a home with the luxury of renting out additional units, this three-home property offers countless possibilities.Located on historic Brockway Road, the property spans .58 acres and is lined with mature trees and lush landscaping, creating

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  2414 Brockway Rd, Winston, OR 97496
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  /48

  $749,900 Sold Jun 30, 2025

  263 NE Brosi Orchard Rd, Winston, OR 97496

  • 4 Beds
  • 2.5 Baths
  • 2,358 Sq Ft
  • Built 2010

  Last Sold Summary

  • $318/SF
  • 7 Days On Market

  Current Estimated Value $746,132

  Last Listing Agent Chelsie Siemens Fathom Realty Oregon, LLC

  

  263 NE Brosi Orchard Rd, Winston, OR 97496
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  /28

  Not Listed For Sale

  164 Country Side Ln, Winston, OR 97496

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1975

  

  164 Country Side Ln, Winston, OR 97496

  Last Sold Summary

  • $33/SF
  • 15 Days On Market

  Last Sold Price $50,000

  Last Listing Agent Tracy Grubbs eXp Realty, LLC
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  /48

  $469,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft

  109 Citation Ct, Winston, OR 97496

  Welcome to 109 Citation Ct, a brand-new single-level home nestled in the highly sought-after Lookingglass Creek Estates subdivision in Winston, Oregon. This contemporary ranch-style residence offers 3 bedrooms, 2 bathrooms, and 1,770 sq. ft. of beautifully designed living space on a .20-acre lot with RV parking behind a private gate. Step inside to find luxury vinyl plank flooring, vaulted

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  109 Citation Ct, Winston, OR 97496
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  /48

  $465,000 Sold Mar 06, 2026

  13224 Lookingglass Rd, Winston, OR 97496

  • 4 Beds
  • 2 Baths
  • 2,534 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $184/SF
  • 202 Days On Market

  Current Estimated Value $463,350

  Last Listing Agent Deleta Dickson eXp Realty, LLC

  

  13224 Lookingglass Rd, Winston, OR 97496
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  /28

  Est $414,609 Not Listed For Sale

  118 Watusi Ct, Winston, OR 97496

  • 3 Beds
  • 2 Baths
  • 1,688 Sq Ft
  • Built 2017

  

  118 Watusi Ct, Winston, OR 97496

  Last Sold Summary

  • 12% Above List Price
  • $219/SF
  • 82 Days On Market

  Last Sold Price $370,000

  Last Listing Agent Linda Jacobson Harcourts Integrity Team Real Estate Services, LLC.
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  /47

  $499,900

  • 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
• 

  

  /9

  $130,000 Sold Jul 31, 2025

  250 SW Ford Ave, Winston, OR 97496

  • 2 Beds
  • 1 Bath
  • 1,012 Sq Ft
  • Built 1953

  Last Sold Summary

  • 43% Below List Price
  • $128/SF
  • 178 Days On Market

  Current Estimated Value $162,206

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

  

  250 SW Ford Ave, Winston, OR 97496
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  /21

  Not Listed For Sale

  124 SE Estate Loop, Winston, OR 97496

  • 3 Beds
  • 1 Bath
  • 924 Sq Ft
  • Built 1975

  

  124 SE Estate Loop, Winston, OR 97496

  Last Sold Summary

  • $22/SF
  • 48 Days On Market

  Last Sold Price $20,000

  Last Listing Agent Julie Bancroft The Neil Company Real Estate
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  /7

  $734,000

  • 4 Beds
  • 2.5 Baths
  • 2,362 Sq Ft

  1068 Rice Creek Rd, Winston, OR 97496

  This gated, 8.52-acre property is fenced and cross-fenced, offering plenty of country living space. This beautiful ranch-style home features updates, a newer roof, and recent interior and exterior paint. The gourmet kitchen includes double ovens and a walk-in pantry. The large living room features a fireplace. The huge primary bedroom includes a walk-in closet and a two-headed shower. One of the

  Greg Johnson G Stiles Realty

  1068 Rice Creek Rd, Winston, OR 97496
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  /41

  $98,000 Sold Aug 20, 2025

  110 NW Broc Dr, Winston, OR 97496

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

  Last Sold Summary

  • $76/SF
  • 25 Days On Market

  Last Listing Agent Anthony Beckham Different Better Real Estate

  

  110 NW Broc Dr, Winston, OR 97496
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  /39

  Est $340,724 Not Listed For Sale

  213 NE Plum Ridge Dr, Winston, OR 97496

  • 3 Beds
  • 2 Baths
  • 1,466 Sq Ft
  • Built 2004

  

  213 NE Plum Ridge Dr, Winston, OR 97496

  Last Sold Summary

  • 4% Above List Price
  • $223/SF
  • 162 Days On Market

  Last Sold Price $326,900

  Last Listing Agent Julie Bancroft The Neil Company Real Estate
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  /41

  $499,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,089 Sq Ft

  160 Wil Way, Winston, OR 97496

  OPEN HOUSE! Sunday 3/29 1-3pm New Home by JW Construction Inc.This beautiful one-level home offers just over 2,000 square feet with three bedrooms and two and a half bathrooms. The open great room features vaulted ceilings, luxury vinyl plank flooring, recessed lighting, and a gas fireplace. A large sliding door opens to an expansive deck, perfect for entertaining or relaxing. The kitchen is

  Tyler Head Turning Point Realty Group

  

  160 Wil Way, Winston, OR 97496
• 

  

  /20

  $184,400 Sold May 23, 2025

  338 NW Civil Bend Ave, Winston, OR 97496

  • 1 Bed
  • 1 Bath
  • 728 Sq Ft
  • Built 1952

  Last Sold Summary

  • 3% Above List Price
  • $253/SF
  • 40 Days On Market

  Current Estimated Value $185,592

  Last Listing Agent Aaron Daniel Lamonte Real Estate Professionals

  

  338 NW Civil Bend Ave, Winston, OR 97496

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