Winston, OR Homes

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  /83

  $735,000

  $50K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,722 Sq Ft

  9114 Old Highway 99 S, Winston, OR 97496

  Escape to the peace and beauty of rural Oregon with this beautifully remodeled country retreat set on 5.4 usable acres of fenced pastureland. Offering the perfect blend of modern comfort and small-acreage functionality, this stunning single-level home features 2,722 sq. ft. with 3 bedrooms, 3 full baths, and a versatile flex space ideal for a home office or hobby room. Each bedroom includes its

  

  Kristina Scott

  Umpqua Legacy Realty LLC

  (458) 310-3863

  9114 Old Highway 99 S, Winston, OR 97496
• Explore Winston

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  /34

  $2,495 Per Month

  • 5 Beds
  • 2 Baths
  • 2,560 Sq Ft
  • 6+ Bdrm Home Built 1895. Close In. With Pastures.

  120 Winston Section Rd, Winston, OR 97496

  A house with a history. 1895 Home with 5+ bedrooms and lots of charm. This home has been in the family for 50+ years. 5+ Bdrm home. Built in 1895. On the River. Close In. Bedrooms/Bonus: 2 Small bedrooms are in attic, three are on 2nd floor. There are three "extra" rooms on first floor that have been used in the past as an office, music room, master bedroom, playroom,

  120 Winston Section Rd, 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 $205,703

  Last Listing Agent Jody Tatone RE/MAX Integrity

  

  50 NE Ronald St, Winston, OR 97496
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  /39

  Est $392,930

  Not Listed For Sale

  401 Serengeti Dr, Winston, OR 97496

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft
  • Built 2017

  

  401 Serengeti Dr, Winston, OR 97496

  Last Sold Summary

  • 15 Days On Market
• 

  

  

  /15

  $185,000

  $90K PRICE DROP

  • 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

  Faas Realty

  (458) 224-5797

  

  0 Wil Way Unit 24278136, Winston, OR 97496
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  /12

  $2,600 Per Month

  • 3 Beds
  • 2 Baths
  • 1,586 Sq Ft
  • Brand New House in Winston!

  105 Citation Ct, Winston, OR 97496

  Discover this brand new 3 bedroom, 2 bath home in Winston. Offering practical living and convenient amenities. The kitchen includes a range, refrigerator, dishwasher, garbage disposal and a cupboard pantry for organized storage. A ceiling fan helps circulate air throughout the living areas, while an included washer and dryer add laundry convenience. Step outside to a fenced yard and covered

  105 Citation Ct, Winston, OR 97496
• 

  

  /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 $329,378

  Last Listing Agent Benjamin Tatone Roseburg Realty

  

  119 Lebleu Ln, Winston, OR 97496
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  /33

  Est $441,157

  Not Listed For Sale

  901 Byron Creek Rd, Winston, OR 97496

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1998

  

  901 Byron Creek Rd, Winston, OR 97496

  Last Sold Summary

  • 22 Days On Market
• 

  

  /45

  $314,900

  • 3 Beds
  • 2 Baths
  • 1,156 Sq Ft

  301 NW Midway St, Winston, OR 97496

  Beautifully remodeled home on almost half an acre right in the heart of Winston! Fully fenced for kids and pets to roam freely. Backyard is ready for someone to make it their own. Work shed in the back with power and lighting for those special projects. Along with a good sized garage for plenty of parking. The home was remodeled top to bottom. As you enter, notice the excellent natural lighting

  

  Ashton Faas

  Faas Realty

  (458) 646-4901

  

  301 NW Midway St, Winston, OR 97496
• 

  

  /20

  $1,225 Per Month

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  550 SE Center St, Winston, OR 97496

  Tentatively available early July. This rental is a 3 bedroom duplex located off Thompson in Winston. There is a gas range, refrigerator, and dishwasher as well as a gas water heater and laundry hookups. Baseboard heat and there is a single car garage and a nice sized yard. Water, sewer, and garbage are paid, you may ask about pets and we do not allow smoking inside any of our

  550 SE Center St, 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 $141,077

  Last Listing Agent Elisa Doudna Pacific Properties

  

  600 SE Edgewood St, Winston, OR 97496
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  /41

  Est $296,492

  Not Listed For Sale

  73 NE Ronald St, Winston, OR 97496

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 1997

  

  73 NE Ronald St, Winston, OR 97496

  Last Sold Summary

  • 137 Days On Market
• 

  

  /15

  $185,000

  $90K PRICE DROP

  • 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

  Faas Realty

  (458) 217-1693

  

  0 Wil Way Unit 24292479, Winston, OR 97496
• 

  

  /17

  $2,600 Per Month

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft
  • Brand New House in Winston! 1 Year Lease Required

  109 Citation Ct, Winston, OR 97496

  Discover this new 3-bedroom, 2-bath home in Winston. The layout offers a functional kitchen equipped with a range, microwave, dishwasher and refrigerator, while a garage and off-street parking provide convenient vehicle space. Washer and dryer are included for easy laundry, and utilities for water and sewer are paid. The property includes a fenced yard with yard maintenance paid, creating a

  109 Citation Ct, 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 $230,197

  Last Listing Agent Shea Wheeler RE/MAX Integrity

  

  563 Medicine Wheel Way, 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

  • 32 Days On Market
• 

  

  /27

  $350,000

  $22K PRICE DROP Pending

  • 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
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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 $160,658

  Last Listing Agent Judith Zuver Winston Realty & Insurance

  

  31 SE Darrell Ave, Winston, OR 97496
• 

  

  /19

  Est $353,445

  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

  • 13 Days On Market
• 

  

  /28

  $350,000

  $150K PRICE DROP

  • 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

  Faas Realty

  (458) 310-3411

  

  0 Wil Way Unit 24094727, Winston, OR 97496
• 

  

  /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 Real Broker

  

  311 Bremner Ln, Winston, OR 97496
• 

  

  /6

  Est $557,450

  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

  • 214 Days On Market
• 

  

  /40

  $499,900

  New Construction $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,999 Sq Ft

  150 Wil Way, Winston, OR 97496

  Open House 5/30 2-5 pm New Home by JW Construction Inc. This beautifully crafted 2,143 sq ft home offers 3 bedrooms and 2 1/2 bathrooms with a thoughtful layout and excellent separation of space. Set on a low-maintenance lot with views of trees and the surrounding mountains, 140 Wil Way combines modern design with comfort and convenience. The open-concept main level features high ceilings,

  

  Tyler Head

  Turning Point Realty Group

  (458) 309-4957

  

  150 Wil Way, Winston, OR 97496
• 

  

  /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 $290,915

  Last Listing Agent Sabrina Jorgensen The Neil Company Real Estate

  

  400 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

  • 2 Days On Market
• 

  

  /44

  $499,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,576 Sq Ft

  2581 NW Brockway Rd, Winston, OR 97496

  Open House 5/30 2-5pm New listing! This beautifully crafted new construction home offers 2,576 square feet with 3 bedrooms and 2.5 bathrooms, thoughtfully designed with quality finishes and modern comfort throughout.The open-concept floor plan features vaulted ceilings, abundant natural light, and recessed lighting, creating a bright and inviting living space. The kitchen is designed for both

  

  Tyler Head

  Turning Point Realty Group

  (458) 291-0968

  

  2581 NW Brockway Rd, Winston, OR 97496
• 

  

  /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 $408,377

  Last Listing Agent Jacob Gilman The Neil Company Real Estate

  

  631 SE Rose Ridge Dr, Winston, OR 97496
• 

  

  /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

  • 20 Days On Market
• 

  

  /41

  $499,900

  New Construction $25K PRICE DROP

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

  160 Wil Way, Winston, OR 97496

  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 designed for both style and

  

  Tyler Head

  Turning Point Realty Group

  (458) 299-7413

  

  160 Wil Way, Winston, OR 97496
• 

  

  /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 $756,848

  Last Listing Agent Chelsie Siemens RE/MAX Integrity

  

  263 NE Brosi Orchard Rd, Winston, OR 97496
• 

  

  /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

  • 3 Days On Market
• 

  

  /48

  $375,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,613 Sq Ft

  186 Woodduck St, Winston, OR 97496

  Well-maintained home in a quiet neighborhood in the heart of Winston. Move-in ready with brand new floors recently installed. Minimal outdoor maintenance. Garden shed and room to park a 5th wheel. Don’t miss your opportunity to own a solid, easy-living home in a great location.

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  186 Woodduck St, Winston, OR 97496
• 

  

  /39

  $230,000

  Sold May 20, 2026

  617 Poison Oak Dr, Winston, OR 97496

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1972

  Last Sold Summary

  • 23% Below List Price
  • $218/SF
  • 160 Days On Market

  Current Estimated Value $224,812

  Last Listing Agent Bob Lamonte Lamonte Real Estate Professionals

  

  617 Poison Oak Dr, Winston, OR 97496
• 

  

  /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

  • 15 Days On Market
• 

  

  /48

  $439,900

  New Construction Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,629 Sq Ft

  260 SE Logan St, Winston, OR 97496

  *** BUILDER INCENTIVE *** Lower Payments Available on this House! Seller offering flexible buyer incentives with acceptable offer, including potential rate buy down, closing cost assistance, or improvement credits. Attractive opportunity for both financed and cash buyers.*** There’s something special about stepping into a home that’s never been lived in—where everything is fresh, thoughtfully

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  260 SE Logan St, Winston, OR 97496
• 

  

  /25

  $95,000

  Sold May 14, 2026

  130 Stephanie Ct, Winston, OR 97496

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2000

  Last Sold Summary

  • $71/SF
  • 5 Days On Market

  Last Listing Agent Jason Mann J Mann Realty

  

  130 Stephanie Ct, Winston, OR 97496
• 

  

  /28

  Est $417,410

  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

  • 82 Days On Market
• 

  

  /36

  $409,000

  $30K PRICE DROP Pending

  • 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
• 

  

  /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 $458,395

  Last Listing Agent Deleta Dickson eXp Realty, LLC

  

  13224 Lookingglass Rd, Winston, OR 97496
• 

  

  /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

  • 48 Days On Market

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