Douglas, OR Homes

• 

  

  

  /28

  $430,000

  • Land
  • 7 Acres
  • $58,108 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
• 

  

  

  /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
• 

  

  

  /9

  $130,000 Sold Jul 31, 2025

  • 1,012 Sq Ft
  • $128/SF
  • 178 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1953

  250 SW Ford Ave, Winston, OR 97496

  Newer Roof nice sized lot in an established neighborhood in Winston, OR. This Home is looking for a craftsman to turn it into its better self. The house is very Livable but non-permitted work has been done. "NOT FINACEABLE" with traditional terms, maybe a hard money loan. Call today for an appointment to visit with your investor or contractor.

  Dawn Trapalis Harcourts Integrity Team Real Estate Services, LLC.

  

  250 SW Ford Ave, Winston, OR 97496
• 

  

  

  /32

  Not Listed For Sale

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

  125 SE Estate Loop, Winston, OR 97496

  

  125 SE Estate Loop, Winston, OR 97496
• 

  

  

  /41

  $650,000 Pending

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

  1260 Ireland Rd, Winston, OR 97496

  Country Retreat on 10.02 acres. The Perfect blend of luxury and privacy in southern Oregon. This custom built 2600 square ft. home offers 3 bedrooms and 2 bathrooms. Step inside to an inviting open floor plan featuring vaulted ceilings and elegant finishes. The gourmet kitchen is a chef's dream, complete with premium appliances, custom cabinets and s spacious island perfect for hosting. The

  

  Daniel Siler

  Engel & Volkers West Portland

  (458) 232-4863

  

  1260 Ireland Rd, Winston, OR 97496
• 

  

  /48

  $418,000 Sold Jul 25, 2025

  • 1,808 Sq Ft
  • $231/SF
  • 10 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1986

  235 NE Main St, Winston, OR 97496

  Welcome to your dream home! This stunning 4-bedroom, 2.5-bath house is nestled on a picturesque piece of property, with valley and mountain views! The home features spacious and airy living areas bathed in natural sunlight, a cozy new wood burning stove perfect for chilly evenings, and an open eat-in kitchen with granite countertops and ample storage. The expansive 21x19 4th bedroom with private

  Julie Bancroft The Neil Company Real Estate

  

  235 NE Main St, Winston, OR 97496
• 

  

  /44

  Not Listed For Sale

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

  127 Country Side Ln, Winston, OR 97496

  

  127 Country Side Ln, Winston, OR 97496
• 

  

  /7

  $299,000 Pending

  • Land
  • 33 Acres
  • $9,133 per Acre

  0 Ireland Rd, Winston, OR 97496

  Fantastic opportunity to create your own private oasis. This private property is situated up in the hills of Winston with great views of the valley. 2 potential building sites for you to choose from. Additionally, there is marketable timber as well. You don't want to miss out on this great opportunity!

  

  Daniel Siler

  Engel & Volkers West Portland

  (458) 218-8471

  

  0 Ireland Rd, Winston, OR 97496
• 

  

  /35

  $17,000 Sold Jul 23, 2025

  • Land
  • 0.14 Acre
  • $121,429 per Acre

  • 172 Days On Market

  111 SE Lebleu Ln, Winston, OR 97496

  Opportunity awaits at 111 Lebleu, a beautiful lot with breathtaking views! This property offers a unique setting for building your dream home with panoramic vistas. The gentle slope provides the perfect canvas for a custom-designed home that maximizes both the views and the natural landscape.US Bank is offering both lot and construction loans, making this an excellent option for those ready to

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  111 SE Lebleu Ln, Winston, OR 97496
• 

  

  /17

  Not Listed For Sale

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

  123 Twin Oaks Loop, Winston, OR 97496

  

  123 Twin Oaks Loop, Winston, OR 97496
• 

  

  /39

  $439,000

  • 3 Beds
  • 2 Baths
  • 1,310 Sq Ft

  441 NW Galaxy Dr, Winston, OR 97496

  Finished heated shop • Finished heated/cooled garage • Stunning views • Beautiful home overlooking the city w/panoramic views of surrounding mountains and valleys. Multiple decks and thoughtfully designated outdoor spaces for entertaining or relaxation. Fully finished and heated shop w/ vaulted ceilings, skylight and wood beams seamlessly attached to the fully finished heated/cooled garage

  

  Nichole Sharman

  Works Real Estate

  (458) 854-7182

  

  441 NW Galaxy Dr, Winston, OR 97496
• 

  

  /46

  $290,000 Sold Jul 18, 2025

  • 1,200 Sq Ft
  • $242/SF
  • 36 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  400 SE Darrell Ave, Winston, OR 97496

  Charming 3-Bedroom Home with Open Floor Plan & Private Outdoor Oasis!Welcome to this delightful 3-bedroom, 1-bath home offering 1,200 sq ft of comfortable, single-level living with an open floor plan that feels bright, spacious, and welcoming. The layout is accessible for most needs, making daily living simple and convenient.The third bedroom is currently open without a door—ideal for a home

  Sabrina Calleen Fathom Realty Oregon, LLC

  

  400 SE Darrell Ave, Winston, OR 97496
• 

  

  /32

  Est $379,642 Not Listed For Sale

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

  220 NE Rose Ridge Dr, Winston, OR 97496

  

  220 NE Rose Ridge Dr, Winston, OR 97496
• 

  

  /45

  $799,500

  • 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
• 

  

  /35

  $465,000 Sold Jul 15, 2025

  • 1,754 Sq Ft
  • $265/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  271 Woodland Dr, Winston, OR 97496

  Check out this quiet & peaceful 3 bedroom, 2 bath, 1754 square foot home. The kitchen has Corian countertops, backsplash and island. Newer stainless steel appliances. Cabinets have pull-outs for easy access. Pantry in kitchen. The kitchen flows into the dining area. Living room has fireplace and slider to deck. Lots of double-pane vinyl windows to enjoy the outdoors. Potential for two primary

  Patrice Glasscock Walt Gayner Real Estate

  

  271 Woodland Dr, Winston, OR 97496
• 

  

  /28

  Not Listed For Sale

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

  164 Country Side Ln, Winston, OR 97496

  

  164 Country Side Ln, Winston, OR 97496
• 

  

  /46

  $479,900

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

  13224 Lookingglass Rd, Winston, OR 97496

  Experience the unique allure of this beautifully updated, original homestead farmhouse nestled in Safari Estates. Thoughtful remodel and tasteful updates have modernized this 1900-built farmhouse, preserving its character while enhancing comfort. With 2,516 sq ft of living space, four bedrooms, and two full baths, this home blends historic charm with modern comfort. The kitchen has been remodeled

  

  Deleta Dickson

  eXp Realty, LLC

  (458) 237-8628

  

  13224 Lookingglass Rd, Winston, OR 97496
• 

  

  /30

  $99,900 Sold Jul 14, 2025

  • 1,188 Sq Ft
  • $84/SF
  • 34 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2005

  311 Bremner Ln, Winston, OR 97496

  Welcome to this well-maintained 2005 double-wide manufactured home, offering 2 bedrooms, 2 bathrooms, and 1,188 square feet of comfortable living space. The open-concept kitchen features generous cabinetry, a spacious pantry, and direct access to a convenient laundry room with another pantry. Situated in the Bremner Hills Co-op Community, the association must approve prospective buyers. Enjoy the

  Cindi Mills RE/MAX Integrity

  

  311 Bremner Ln, Winston, OR 97496
• 

  

  /28

  Est $422,569 Not Listed For Sale

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

  118 Watusi Ct, Winston, OR 97496

  

  118 Watusi Ct, Winston, OR 97496
• 

  

  /15

  $230,000

  • Land
  • 4.26 Acres
  • $53,991 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
• 

  

  /47

  $358,400 Sold Jul 11, 2025

  • 1,250 Sq Ft
  • $287/SF
  • 224 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2020

  149 Teresa Ln, Winston, OR 97496

  Adorable newer home situated on a quiet street in Winston with mountain views. This home features laminate flooring flowing throughout the main living area, energy efficient mini splits, and an open floor plan. The kitchen includes stainless steel appliances, granite counter tops, and a large island. The primary suite has plush carpet, full bathroom with walk-in shower and granite counter tops.

  Jennifer Kramer RE/MAX Integrity

  

  149 Teresa Ln, Winston, OR 97496
• 

  

  /32

  Est $821,000 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,052 Sq Ft

  350 Woodland Dr, Winston, OR 97496

  

  350 Woodland Dr, Winston, OR 97496
• 

  

  /15

  $230,000

  • Land
  • 3.14 Acres
  • $73,248 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
• 

  

  /31

  $79,000 Sold Jul 10, 2025

  • 1,300 Sq Ft
  • $61/SF
  • 28 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1999

  155 NW Broc Dr, Winston, OR 97496

  Affordable Living in an All-Age Community – Low Space Rent!Welcome home to this charming 3-bedroom, 2-bath manufactured home located in a welcoming all-age community with an incredibly low space rent of just $449/month!Step inside to find a comfortable layout, and enjoy peace of mind knowing the roof is only about a year old. Outside, you'll love the spacious yard featuring pear and plum trees.

  Rachel Sturdevant eXp Realty, LLC

  

  155 NW Broc Dr, Winston, OR 97496
• 

  

  /21

  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 924 Sq Ft

  124 SE Estate Loop, Winston, OR 97496

  

  124 SE Estate Loop, Winston, OR 97496
• 

  

  /47

  $325,000

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

  465 SE Gregory Dr, Winston, OR 97496

  Welcome to this inviting single-level home in Winston, Oregon! Built in 2021, this 3-bedroom, 2-bathroom residence offers 1,620 square feet of bright, open living space. The spacious living room seamlessly connects to a dining area and well-equipped kitchen with a center island, pantry, and all major appliances—perfect for entertaining or everyday comfort. Step through double doors to enjoy a

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  465 SE Gregory Dr, Winston, OR 97496
• 

  

  /28

  $389,000 Sold Jul 03, 2025

  • 1,468 Sq Ft
  • $265/SF
  • 15 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2016

  765 SE Lanola St, Winston, OR 97496

  Beautifully maintained single-level home sits on a prime corner lot with sweeping views of the valley and surrounding mountains. Just a mile down the road, you'll find Brosi Sugartree Farms - a local favorite for fresh produce, seasonal events, and a true taste of the area's charm. Inside, you're welcomed by an open airy layout with plenty of natural light. The mix of laminate and tile flooring

  Jacob Gilman The Neil Company Real Estate

  

  765 SE Lanola St, Winston, OR 97496
• 

  

  /39

  Est $353,447 Not Listed For Sale

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

  213 NE Plum Ridge Dr, Winston, OR 97496

  

  213 NE Plum Ridge Dr, Winston, OR 97496
• 

  

  /47

  $399,900

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

  621 SE Rose Ridge Dr, Winston, OR 97496

  Welcome to 621 SE Rose Ridge Dr in Winston’s desirable Orchard View neighborhood—a beautifully maintained single-level home built in 2020. This 3-bedroom, 2-bath home offers approximately 1,620 sq ft of thoughtfully designed living space on a landscaped 6,534 sq ft lot. The open-concept great room features vaulted ceilings, while the gourmet kitchen includes solid surface countertops, a stainless

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  621 SE Rose Ridge Dr, Winston, OR 97496
• 

  

  /40

  $320,000 Sold Jul 03, 2025

  • 1,374 Sq Ft
  • $233/SF
  • 113 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2004

  401 Sunnyside Dr, Winston, OR 97496

  MOTIVATED SELLER! Bring all offers! Step into this charming 3-bedroom, 2-bathroom home, built in 2004, and perfectly situated on a quiet dead-end street on the outskirts of Winston—just moments from fresh fruits and vegetables at Brosi Sugartree Farms! This well-maintained, move-in-ready home boasts vaulted ceilings, warm laminate floors, and large windows that fill the living and dining areas

  Anthony Beckham Different Better Real Estate

  

  401 Sunnyside Dr, Winston, OR 97496
• 

  

  /47

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  258 NW Bree Dr, Winston, OR 97496

  

  258 NW Bree Dr, Winston, OR 97496
• 

  

  /37

  $400,000

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  360 NE Rose Ridge Dr, Winston, OR 97496

  Beautiful 3BD/2BTH home in Winston’s sought-after Rolling Meadows neighborhood! Built by Avery Homes in 2021, this one-level residence feels "like new" and is completely move-in ready. Enjoy an open-concept layout with durable LVP flooring, quartz countertops, and a bright, spacious living area perfect for everyday activities and entertaining. Energy-efficient solar panels installed in July 2024

  Aaron Cherry Oregon Life Homes

  

  360 NE Rose Ridge Dr, Winston, OR 97496
• 

  

  /48

  $749,900 Sold Jun 30, 2025

  • 2,358 Sq Ft
  • $318/SF
  • 7 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2010

  263 NE Brosi Orchard Rd, Winston, OR 97496

  Park-Like Retreat with Panoramic Views & Dream Shop on 1.82 Acres.Welcome to your single-level sanctuary offering comfort, elegance, and functionality in a serene, park-Like setting. This thoughtfully designed 4-bedroom, 2 bathroom home showcases a spacious open floor plan, durable LVP flooring throughout, and a beautifully appointed kitchen featuring custom cabinetry, quartz countertops, and a

  Chelsie Siemens Keller Williams Southern Oregon-Umpqua Valley

  

  263 NE Brosi Orchard Rd, Winston, OR 97496
• 

  

  /27

  Est $373,471 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  139 Teresa Ln, Winston, OR 97496

  

  139 Teresa Ln, Winston, OR 97496
• 

  

  /31

  $59,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  111 Sharway Ln, Winston, OR 97496

  This charming 2-bedroom, 1-bath manufactured home is fully furnished and move-in ready, located in a well-kept 55+ community with low space rent, offering an ideal mix of comfort and convenience. The property includes a recently built carport, two storage sheds, and a beautifully landscaped yard that enhances its curb appeal. With a roof that’s just 5 years old and a brand-new HVAC system

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  111 Sharway Ln, Winston, OR 97496
• 

  

  /22

  $255,000 Sold Jun 27, 2025

  • 1,296 Sq Ft
  • $197/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2000

  314 NW Civil Bend Ave, Winston, OR 97496

  This 3-bed, 2-bath home, built in 2000, features vaulted ceilings and an open concept, perfect for modern living. It needs TLC but offers great potential to build sweat equity. Enjoy a spacious layout with a large kitchen, soaking tub, fenced yard, and RV parking. A perfect opportunity to customize and create your dream home!

  Karina DiStefano Lamonte Real Estate Professionals

  

  314 NW Civil Bend Ave, Winston, OR 97496
• 

  

  /32

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,512 Sq Ft

  Unlisted Address

  

  Unlisted Address
• 

  

  /46

  $469,900 Pending

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

  113 Citation Ct, Winston, OR 97496

  Welcome to 113 Citation Ct, Winston, OR 97496! This brand-new home in the desirable Lookingglass Creek Estates offers modern style and quality craftsmanship throughout. Enjoy a bright, open layout with vaulted ceilings and upscale finishes, including soft-close cabinetry, sleek quartz countertops, a spacious pantry, and durable luxury vinyl plank flooring. The private primary suite features a

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  113 Citation Ct, Winston, OR 97496
• 

  

  /43

  $165,000 Sold Jun 25, 2025

  • 800 Sq Ft
  • $206/SF
  • 52 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1970

  600 SE Edgewood St, Winston, OR 97496

  This 1970 manufactured home sits on a spacious 0.43-acre lot, offering plenty of room to enjoy the outdoors. Featuring a durable metal roof, covered porches, and a carport with an attached tool shed, this property is well-equipped for both convenience and functionality. Additional highlights include a parking pad, multiple outbuildings, and fruit trees, all within a fully fenced yard for added

  Elisa Doudna Pacific Properties

  

  600 SE Edgewood St, Winston, OR 97496
• 

  

  /41

  Est $446,859 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,730 Sq Ft

  430 Serengeti Dr, Winston, OR 97496

  

  430 Serengeti Dr, Winston, OR 97496

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