Winston, OR Homes

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  /45

  $699,500

  • 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
• 

  

  

  /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
• 

  

  

  /21

  $359,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,348 Sq Ft

  595 SE Parkway Dr, Winston, OR 97496

  Exquisitely clean and well-maintained single-level home in desired Winston neighborhood close to schools and parks. Very sharp, low-maintenance landscaping with small grassy area in the back and mature shrubs and perennials throughout the property. This home was built in 1996 but looks almost brand new. Offering 3 bedrooms, 2 full bathrooms, vaulted living room, vinyl windows, dark wood laminate

  Jacob Gilman The Neil Company Real Estate

  

  595 SE Parkway Dr, Winston, OR 97496
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  /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
• 

  

  

  /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
• 

  

  /45

  $275,000 Sold Sep 12, 2025

  • 1,005 Sq Ft
  • $274/SF
  • 67 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  400 NW Susan Ave, Winston, OR 97496

  Charming and remodeled, this cozy 3-bedroom, 2-bath home offers comfortable single-level living on a quiet corner lot. Enjoy updates throughout, including a composition roof, ductless heat pump, and updated flooring—all installed in 2020. The open and functional layout is complemented by an attached 1-car garage for convenience. Step outside to a fully fenced backyard featuring a storage shed,

  Shane Mast Oregon Life Homes

  

  400 NW Susan Ave, Winston, OR 97496
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  /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
• 

  

  /15

  $200,000

  • Land
  • 4.26 Acres
  • $46,948 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
• 

  

  /48

  $425,000 Sold Sep 12, 2025

  • 2,167 Sq Ft
  • $196/SF
  • 139 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2007

  7941 Upper Olalla Rd, Winston, OR 97496

  Beautiful 5.01 acre property with 2007 rebuilt home! Lots of flat ground for vegetable/flower garden. Fenced and cross fenced. 2 - 1200 gallon holding tanks. New water softener. Year-round creek. Large drive-thru shop with 3 - 12ft doors and 3 stall barn. Huge metal building for many uses. Plus, 2 sheds and 1 fort. Lots of room for animals and toys!

  Carol Williams The Neil Company Real Estate

  

  7941 Upper Olalla Rd, Winston, OR 97496
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  /32

  Est $357,655 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
• 

  

  /15

  $200,000

  • Land
  • 3.14 Acres
  • $63,694 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
• 

  

  /46

  $469,900 Sold Sep 08, 2025

  • 1,770 Sq Ft
  • $265/SF
  • 97 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  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
• 

  

  /34

  Not Listed For Sale

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

  224 NW Bree Dr, Winston, OR 97496

  

  224 NW Bree Dr, Winston, OR 97496
• 

  

  /28

  $375,000

  • Land
  • 7.4 Acres
  • $50,676 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
• 

  

  /35

  $457,000 Sold Aug 28, 2025

  • 1,994 Sq Ft
  • $229/SF
  • 407 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2020

  197 Wil Way, Winston, OR 97496

  Don't miss this beautifully maintained Custom one level home with 4 bedrooms and 2 bath in Safari Estates. Vaulted ceilings in living room and beautiful mountain east views. Floor plan is open with plenty of natural light. Gas fireplace for those cozy days in the living room. Laminate flooring through out living space with carpet in bedrooms for warmth. Tile flooring in bathrooms with tile shower

  Nancy Wood Oregon Life Homes

  

  197 Wil Way, Winston, OR 97496
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  /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
• 

  

  /39

  $429,900 Pending

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

  441 NW Galaxy Dr, Winston, OR 97496

  Finished heated shop • Finished heated/cooled garage • Stunning views • Primary bedroom on main floor. 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

  

  Nichole Sharman

  Works Real Estate

  (458) 854-7182

  

  441 NW Galaxy Dr, Winston, OR 97496
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  /43

  $299,000 Sold Aug 27, 2025

  • 1,316 Sq Ft
  • $227/SF
  • 36 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  200 SE Darrell Ave, Winston, OR 97496

  Welcome to your brand-new single level home! This beautifully designed residence features an open floor plan that seamlessly connects the spacious living, dining, and kitchen areas—perfect for both everyday living and entertaining. The kitchen features sleek quartz countertops, stainless steel appliances, and ample cabinetry. Luxury vinyl plank flooring flows throughout the main living spaces,

  Jennifer Kramer RE/MAX Integrity

  

  200 SE Darrell Ave, Winston, OR 97496
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  /28

  Est $412,909 Not Listed For Sale

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

  118 Watusi Ct, Winston, OR 97496

  

  118 Watusi Ct, Winston, OR 97496
• 

  

  /48

  $270,000

  • 3 Beds
  • 1.5 Baths
  • 1,412 Sq Ft

  54 NW Rose St, Winston, OR 97496

  First time on the market in over 40 years! Whether you are a first-time home buyer, an investor or someone with a home business that wants to take advantage of the commercial zoning, this property offers a fantastic opportunity at a great price point. Built in 1947, the home carries vintage charm and the potential for updates or personalization. There are three bedrooms, a small office and a

  

  Deleta Dickson

  eXp Realty, LLC

  (458) 302-2153

  

  54 NW Rose St, Winston, OR 97496
• 

  

  /29

  $279,400 Sold Aug 27, 2025

  • 1,005 Sq Ft
  • $278/SF
  • 143 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1989

  520 SE Dawna Ct, Winston, OR 97496

  Take advantage of a fantastic opportunity- sellers are offering a credit to the buyer, which can be used towards closing costs or even a rate buy-down! Conveniently located just a few blocks from Winston Middle School, this home offers 3 bedrooms, 1 bathroom and updates including laminate flooring throughout and a recent heating and air conditioning system. Outside offers an attached garage,

  Ashley Oberman Oregon Life Homes

  

  520 SE Dawna Ct, 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
• 

  

  /37

  $390,000

  • 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
• 

  

  /31

  $399,900 Sold Aug 25, 2025

  • 1,630 Sq Ft
  • $245/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 1996

  660 Mimosa Ct, Winston, OR 97496

  Situated on a quiet cul-de-sac, this move-in-ready features a beautiful kitchen with granite counters, spacious living room and primary bedroom, tile counters and floor in the bathrooms,and an amazing new patio in the large, private backyard. The back yard is ready to be turned into your oasis, and there is a separate area with raised beds for a garden. There is room next to the garage to park an

  Rich Raynor Heritage Real Estate

  

  660 Mimosa Ct, Winston, OR 97496
• 

  

  /39

  Est $345,560 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
• 

  

  /31

  $57,000 Pending

  • 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
• 

  

  /33

  $340,000 Sold Aug 25, 2025

  • 1,798 Sq Ft
  • $189/SF
  • 215 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1956

  40 NW Cary St, Winston, OR 97496

  Completely updated Ranch style home entirely fenced corner lot in City limits of Winston. Property is landscaped and set up for automatic sprinklers and drip systems. Apple trees, grapes (arbor) and planter boxes . Dining/kitchen area has direct access to back patio with BBQ area and small shop. Certified Insert and 2010 Carrier HVAC. Oversize garage, Small shop, 50' RV parking with hookups, Dog

  Beverly Heyer Safari Village Real Estate

  

  40 NW Cary St, 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
• 

  

  /46

  $225,000 Pending

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

  431 NE Darlene St, Winston, OR 97496

  This 3-bedroom, 2-bathroom manufactured home on real property offers 1,620 sq. ft. of comfortable living space with a flexible layout full of potential. The home does need some TLC, but it provides a solid foundation for updates and customization.Inside, you’ll find spacious living areas with sliding doors to the exterior, a kitchen with an island, dishwasher, and refrigerator, plus a dedicated

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  431 NE Darlene St, Winston, OR 97496
• 

  

  /7

  $96,000 Sold Aug 22, 2025

  • 1,296 Sq Ft
  • $74/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1999

  409 NW Broc Dr, Winston, OR 97496

  Sizeable three bedroom two bath manufactured home with newer luxury vinyl Plank flooring, newer kitchen appliances and a great floor plan. Located in the well-maintained Rosewood Mobile Home Park.Desirable location, close to schools and a river park.

  David Moore Oregon Life Homes

  

  409 NW Broc Dr, Winston, OR 97496
• 

  

  /27

  Est $369,103 Not Listed For Sale

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

  139 Teresa Ln, Winston, OR 97496

  

  139 Teresa Ln, Winston, OR 97496
• 

  

  /35

  $220,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft

  141 5th St, Winston, OR 97496

  Charming and cozy 3-bedroom, 1-bath home with a clean interior and a well-designed layout. The inviting living spaces offer warmth and comfort. The kitchen and dining combo are a perfect area to gather at. Step outside to a back deck, great for entertaining. Includes tool and storage shed for added convenience.

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  141 5th St, Winston, OR 97496
• 

  

  /33

  $309,000 Sold Aug 22, 2025

  • 1,126 Sq Ft
  • $274/SF
  • 80 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1979

  420 NW Elizabeth Ave, Winston, OR 97496

  **Back on market due to buyer financing failing, no fault of home. Clean inspection on file. Turn-key & Move-in ready!** Winston charmer with 3 bedrooms, 2 full baths, and a spacious open-concept layout perfect for modern living. The large great room features a cozy fireplace and flows into a generous kitchen with an eat bar, hickory cabinets, and ample workspace—ideal for both daily life and

  Tammi Ellison eXp Realty, LLC

  

  420 NW Elizabeth Ave, Winston, OR 97496
• 

  

  /39

  Est $370,821 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,682 Sq Ft

  209 NE Rose Ridge Dr, Winston, OR 97496

  

  209 NE Rose Ridge Dr, Winston, OR 97496
• 

  

  /47

  $325,000 Pending

  • 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
• 

  

  /16

  $143,000 Sold Aug 21, 2025

  • 864 Sq Ft
  • $166/SF
  • 3 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1955

  Unlisted Address

  Fix this up or live in as is! 3 bedroom, 1 bath home with a single car attached carport with storage. Also, includes a detached 2 car garage/shop as well as another small storage building. Sits on a large flat city lot with ample room to park your RV's or other vehicles. Come See!

  Judith Zuver Winston Realty & Insurance

  

  Unlisted Address
• 

  

  /32

  Not Listed For Sale

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

  Unlisted Address

  

  Unlisted Address
• 

  

  /47

  $399,900 Pending

  • 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
• 

  

  /45

  $305,000 Sold Aug 21, 2025

  • 1,318 Sq Ft
  • $231/SF
  • 32 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  180 SE Darrell Ave, Winston, OR 97496

  Brand New Construction in Winston! Welcome to 180 SE Darrell Ave., a new 3-bedroom, 2-bathroom home offering modern finishes throughout. This move-in ready home features an open floor plan with seamless flow between the kitchen, dining, and living areas—perfect for both entertaining and everyday living. Enjoy cooking in the stylish kitchen with stainless steel appliances, quartz countertops, and

  Jennifer Kramer RE/MAX Integrity

  

  180 SE Darrell Ave, Winston, OR 97496
• 

  

  /41

  Est $437,985 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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